Some of the previous conversations got me thinking about investigating some old Mob hits, and so I also found one old list which I made awhile ago and later placed some additional infos and in no time created this list of the Outfit’s so-called greatest and most fascinating contract killings. By “greatest” or “most fascinating” I’m thinking about the types of professional contract killings, which were executed in a way that no kind of normal person could ever perform. There are all types of various reasons for this kind of murders but the main thing is that the so-called contract killing provides the hiring party with the advantage of not having to commit the actual killing, and above all it’s more difficult for law enforcement to connect them with the murder. It’s not an easy job for someone to execute a contract killing for some dangerous individual over another dangerous individual with the possibility to strike back. For example, one of the first steps for one professional contract killer is to take a series of steps in planning the murder and to prepare himself for either the arranging of transportation for the dead target or to prepare himself for fast action such as “hit and run”. The next step should be the killer’s weapon of choice and his skills in using all kinds of guns, since some Mob killings involve the use of small caliber handguns fired at close range and some obviously involve machineguns or rifles fired from far distances. The next step is locating and following the victim, thus learning the every day routines and during the process, the killer should pick the main killing location and around what time the target will be at that same location. And the final step is obviously carrying out of the actual murder contract.


Now, the Chicago Outfit was known for its own brutal way of handling problems, like for example snatching people right off the streets and the way of previously torturing their victims for several days and later they would usually turn up in some car trunk, while being all tied up in ropes and wires. Or maybe even the old infamous drive-bys which mainly occurred during the days of Prohibition, when the blasts of Tommy guns were heard on daily basis. But during that same old period, and even today, there were some murders which were pulled off by different crime syndicates and were almost unbelievable for the ordinary citizen, like for example the infamous hit on the Jewish Mob boss Bugsy Siegel, which occurred from quite a long distance while blasting one of his eyes few meters from his head, or maybe even the contract killing on Dutch Shultz where one or two guys went in some joint while blasting their guns and killing three or four armed guys. So my point is that I somehow managed to pick some of the most professional hits which these so-called street people, mainly from the Chicago Mob, managed to pull off by showing some type of military or any kind of special skills in the details and the logistics of the contract killings, all mainly backed up by some type of corruption, betrayal or “simple” business tactics. Here’s my personal Top Ten:



10. Giuseppe Esposito a.k.a. Diamond Joe was just one of the so-called creators of the infamous Chicago Outfit, who after Jim Colosimo that was killed in 1920, became the most powerful mobster in the Windy City, especially the West Side. Even though Colosimo’s empire was inherited by a different gang, still during Prohibition, Esposito was the most lucrative bootlegger who somehow controlled or was closely connected to most of the local clans, no matter the ethnicity. But by the mid 1920’s or somewhere around 1926, many up and coming bootleggers from the old Colosimo clan began mixing with up and coming members from the Esposito group on daily basis and they sort of began creating their own criminal “world”. Like for example, two Esposito members Tony Volpe and Paul Ricca became quite close with Al Capone, the guy who at the time inherited Colosimo’s old territory. So my personal opinion is that these fellas possibly saw a larger picture rather than the old timers such as Esposito and allegedly created a plan to eliminate the boss, who in turn wasn’t an easy target. On top of that, I believe that Esposito was connected to many underworld clans or crime families from around the country and maybe even further, so my point is that whoever planned his murder, he or she first had to wait for someone’s approval, possibly fro Mafia bosses or high level gangsters. As I already stated that Diamond Joe Esposito was no easy target for two simple reasons including one being his position as top boss and the second was obviously his experience with some of the former bosses, who in turn were his business partners but ended up six feet under the ground. On top of that, many of Esposito’s so-called soldiers and loyalist were being killed all over town, so story goes that the old boss was changing his routines on daily basis and he always had beside him his two loyal bodyguards the Varchetti brothers who were always armed to the teeth. Now I’m about to show you the main reason for which I believe that people from Esposito’s own crew were involved in the assassination. If we look at the situation clearly, there was no other way for killing the old boss except for spraying hundreds of bullets from a drive-by car, with the possibility of hurting innocent pedestrians, since Esposito was known for constantly having people or children from the neighbourhood around him. Who knows, maybe it was simply one of his own ways of protecting himself from any possible assassination. The year of 1928 was an election year and story goes that Esposito was told to back off, which he obviously refused and knowingly ordered his own death sentence in the eyes of his criminal cohorts from his crew and around the country. So the only possible way of getting to Esposito was the so-called corruption of the main individuals who protected him every day, such as the Varchetti brothers. Story goes that “someone” realised or heard that the Varchettis were allegedly tired of Esposito or even maybe they were scared for their own lives, but above all the two brothers knew that Esposito was going to leave them high and dry after the elections since he was obviously going to lost them. So that same “someone” approached the brothers and asked them about Esposito’s plans in the next few days and also advised them about the plot.


On March 21, 1928, Esposito was escorted out of his house at 800 South Oakley Boulevard by the Varchetti bros and while walking down the street, in his own style, the old boss met an old lady from the neighbourhood and started having a long conversation. When the old lady passed, the trio continued to walk down the street in formation of left and right bodyguard with Esposito in the middle. Suddenly, according to the bodyguards and their wives who lived right across the street, a car with three armed guys showed up and slowly approached behind them. The two bodyguards noticed the car and without any warning, both of them dropped on the ground while leaving old man Esposito alone in front of the killers. The poor guy was riddled with bullets while hopelessly screaming in despair. His screams and the shootings were heard all around the neighbourhood. So as I previously stated that this information comes from the Varchettis and their wives who lived nearby the shooting, which is quite weird that it occurred right in front of their homes and on top of that they were the main witnesses. The next strange thing was that both bodyguards didn’t receive a scratch which was a detail that became very suspicious in the eyes of some of the Chicago detectives. Plus on that same day, both of them forgot their guns, something which never previously occurred and on top of that, they knew about the life threats which Esposito previously received since they were made public. But the most interesting detail of the murder was when later the coroner reported that Esposito had 58 pellets of shotgun shells and various types of pistol bullets, but the main thing was that there was one bullet hole in his right arm, and Esposito was riddled on his left side by the assassins as he was in position of walking down the street. Plus he also had powder burns on his body which indicates that he was shot from close range, which for me personally raises the question on whether the Varchetti brothers were two of the shooters in the Esposito killing. I personally believe that the Varchettis had a job for making sure that Esposito was dead and also to make sure that there were no innocent pedestrians nearby when the shooting occurred. And as the old saying goes, if you want to find the boss’ killer, look for the one who replace him and those two guys were Tony Volpe and Paul Ricca, who in fact were Esposito’s former “right-hand men”.



9. After the murder of Joe Esposito, the so-called Capone Mob was officially formed and also recognized by the other national crime families. A lot of changes occurred such as high level members being brought into the Mafia and the importation of some New York or mainly Brooklyn mobsters still continued. For example, that same year one infamous Brooklyn gangster known as Louis Campagna was brought to Chicago and was absorbed as new member of the newly formed organization, since he was allegedly involved in this next highly professional contract killing of a high level mobster. I’m talking about one of Capone’s alleged former mentors and also a close friend from Brooklyn, New York; known as Francesco Ioele a.k.a. Frankie Yale. You see, Yale was very similar to the late Esposito since he was also one of the most powerful gangsters at the time who was involved in numerous rackets, such as labor racketeering, gambling, dockside extortion and above all bootlegging booze. So story goes that the relationship between Yale and Capone came to decline during the mid 1920’s, when allegedly some of Capone’s people began turning up dead in New York and also many of Capone’s booze trucks began having problems with hijackings. But my personal opinion is that the main problem was for the control over the Unione Sicilani organization in Chicago, which in fact was a battle between Capone and Joe Aiello from the North Side area. The main thing was that Aiello was problem for Capone but he was also problem for the newly formed West Side faction or the former Esposito group, since Aiello also had operations in that same area, especially Taylor St. after exterminating the previous Sicilian clan from that same territory. So all of those ex-Brooklyners, including Capone, expected to be backed up by their old friend Frankie Yale but that didn’t happened. Story goes that during a 1927 meeting in Chicago, Yale told both warring factions to make peace and split the profits, and in the same style as the late Esposito, instantly signed his own death warrant.


Most importantly was that the year of 1928 was also the year when Al Capone literally controlled hundreds of professional shooters and killers from all around the country and had the power to kill anyone around the world, including mayors and presidents, but still Yale was different since he was one of their own and was also a killer in his own right, who controlled his own small army and generated a fortune. In plane words, Capone possibly needed again an approval or assistance from other higher ups within the New York Mafia so he can execute the contract on Yale’s life and again he also needed and inside info regarding Yale’s activities. As any other high profile mobster, Yale always had a couple of armed bodyguards beside him and often stayed at his headquarters which was the Sunrise Club, located at 14th Avenue and 65th Street, New York. So this particular contract killing was a little different from the previous one, since it supposed to occur in a different city instead of their “hometown”. Even though Capone and the West Side faction had close connections in New York, still they controlled a different territory and obviously weren’t aware of Yale’s everyday routines and my personal belief is that the main person who provided the Capone Mob with the needed information was Louis Campagna. As I previously stated that during those days, Capone controlled many hit teams but his main guys regarding the “murder racket” were Tony Capezio, Vincenzo Gibaldi a.k.a. Jack McGurn, John Moore a.k.a. Claude Maddox and William Heeney. You see, Capezio and Gibaldi were both fearless and murderous gangsters and as for Heeney and Maddox, well these two fellas had connections to many professional killers from around the Midwest, who in turn were labelled by the media and press as the “American Boys”. Obviously since Yale was no easy target, the boys decided to use out of town killers and called one of their most skilful associates such as former St. Louis gangster Fred Burke, who in turn supplied the guns and became a member of the hit team, which by now allegedly also included Maddox, Heeney and Campagna. No one knew Burke, Maddox or Heeney around the New York which made them the perfect executioners for the job.


In June that same year, the hit team arrived in the Big Apple and they took an apartment somewhere in Brooklyn and stalked Yale for almost a month, just to learn his everyday routines and to possibly confirm Campagna’s inside info. The main info was that Yale had a new young wife by the name of Lucy and together they had 1 year old daughter. They allegedly knew that Yale was very sensitive and carrying towards Lucy so the hit team decided to take an advantage of his weakness. One Sunday afternoon, on July 1, 1928, Yale was playing cards at his Sunrise Club, located at 14th Avenue and 65th Street, when suddenly he received a cryptic phone call. The caller said something was wrong with Lucy and his daughter and that he should come home fast. In a panic moment, Yale took off with his brown colored Lincoln coupe without his bodyguards. Yale drove up to New Utrecht Avenue, where the hit men in their Buick sedan drove next to him. Yale noticed the hit squad and took off west onto 44th Street, with the Buick close behind him. The chase continued but Yale's car was soon overtaken by the Buick, whose occupants riddled Yale with bullets. Yale lost control of his car and crashed into a stoop of a brownstone at No. 923. He opened the door of his car and fell to ground. One of the hit men got out of their car and pumped few more bullets into Yale’s body. The job was done and the assassins left the scene and drove nearly three blocks away where they abandoned their car and left on foot. Later the cops found the abandoned Buick and inside they found a .38 caliber revolver, a .45 automatic, a sawed-off pump shotgun, and a Thompson submachine gun. Also the cops managed to trace the submachine gun to a Chicago sporting goods dealer named Peter von Frantzius, who in turn was Chicago’s most famous legal guns supplier at the time so it was very hard to tell who bought the gun from him. Later the cops repeatedly questioned Capone and some of his gang associates about the Yale murder, but nothing came of the inquiries.


8. As you can see, the previous examples mostly relayed on good logistics and professional shooters, but above all, the plots mostly relayed on betrayal, which is the main reason on why I placed them on the last two positions. I mean in both contract killings, the victims were betrayed by someone who knew their everyday routes but still they were professionally sprayed with bullets in the right time, and at the right location. So now I want to show you another example in which we can see that the Outfit’s murder tactics took a step further and received some sort of military details by killing their victims from a distant range with the help of some kind of submachine gun, which in reality is quite hard situation to hit your target without killing any innocent people. Well that kind of situation occurred during the early 1930’s, when the days of Prohibition were coming to an end and every possible crime syndicate or Mafia clan was fighting for its spot in the underworld, since their main money supply was about to be finished forever. So my point is that during Prohibition, Al Capone’s main racket was always bootlegging booze and that’s how in fact he went up the ranks in the world of the Mafia. The thing was that many of his non-Italian allies were already being involved in other rackets such as gambling, vending machines or union racketeering, so when the booze racket was coming to an end, Capone wanted in and to tell you the truth in most cases he was obviously welcomed with open arms. So the main problem was that some of those racketeers or mobsters simply wanted to stay as the main overseers of their own rackets, but we all know that’s a “no, no” in the world of the Mafia and that is why many gangsters had to go. One of those fellas was the infamous union racketeer and long-time Capone ally known as George “Red”: Barker, who was deeply involved in the union racketeering business and on top of that, he was a ruthless killer and kidnapper and quite feared member of Chicago’s underworld. Barker was also very close to the rising top administration, such as Paul Ricca but the thing was that Barker had a problem with another rising Capone faction, which was also mostly formed by non-Italians but had way more closer relationship to the Capone administration. In plane words, Barker had problem with Murray Humphreys, the Outfit’s future mastermind and main adviser and also one of Capone’s favourite soldiers at the time. The problem was that they kidnapped some union guy for ransom cash, and after finishing their job, Barker allegedly refused to give his cut to the higher ups within the Capone Mob, which obviously was his ticket to the graveyard. But above all, Barker’s real problem with the Caponites was his close association with one of their enemies in the union and vending machine rackets, known as Roger Touhy.


On June 6, 1932, the boys sent one couple to act as newly married lovers on a second floor apartment at 1502 North Crawford Av., which in fact was an area often visited by Barker since there were many gambling joints and also athletic clubs nearby who paid their street taxes to him. Since the married couple was only a front for the owners, I believe that some of the boys also stayed in that same apartment from time to time and watched Barker’s everyday movements and waited for the right moment. On June 17, Barker was walking along that same street with a couple of friends after watching a boxing match in one the nearby athletic clubs, when suddenly from across the street hundreds of bullets bursted into Barker’s body while miraculously leaving the rest of his friends untouched. I mean it was an unbelievable situation in which from 10 or 20 meters across the street, from a second floor apartment, someone managed to riddle Barker’s body with bullets, while the people, two men and one woman, who stood only centimetres from him, remained unharmed. While Barker’s friends lay on the ground, a car with three men pulled over and one of those guys came out of the auto and pulled out a huge stack of cash from one Barker’s pockets, returned into the car and the trio sped off in unknown direction. After that, Barker’s friends dragged him into their car and took him to the nearest hospital but obviously it was too late. Later the cops obviously checked the apartment from across and managed to only one Thompson machinegun, which after the ballistic tests showed that it was the same weapon used in the killing. Later some of the investigators also found a makeshift target range close to a drainage canal near the Stickney area and according to many witnesses, a couple of men were seen there shooting a Thompson at a 12 inch post the very same day before Barker was killed. The gun was later traced to the Haber Screw machine company who purchased the gun at Von Lengerke & Antoine sporting goods, located at 33 South Wabash. They also checked the names of the alleged married couple and they were not surprised and they found out that they were false. In reality, Barker was a very smart racketeer but he was also very reckless in the eyes of the Capone Mob and so there was little mystery behind his execution, since even the rats in the sewers speculated that the Capone Mob was behind it. In no time, the newspapers declared that, according to “underground rumours”, for some months before his murder, Barker often hung around with William ”Three Fingers Jack” White and Murray Humphreys, and allegedly formed a triumvirate with the intention of taking over extensive liquor and gambling territories held by the Touhy gang, or in other words they tried to blame Barker as if he betrayed his own clan. It was all lies since years later Humphreys unknowingly talked about the Barker situation in front of a hidden wiretap and confirmed that the Capone Mob was involved in the hit, since the guys who were in the car and took Barker’s money were in fact Claude Maddox, William White and Sam Alex.



7. The seventh place goes for the “clean and neat” type of contract killing in which the victim’s attention is turned by some kind of diversion, while someone places a gun behind the head of that same victim and pulls the trigger. For example, this kind of style is often used when the victim or the target is also quite skilful or quite dangerous and if something goes wrong, he or she can easily retaliate in a matter of seconds. You see, sometimes there are type of targets who can easily duck and simply escape a hale of bullets since they already have been in the same kind of situations and lived by the minute and are always ready. According to some stories, the previously mentioned Jack McGurn was one those skilful fellas who allegedly never achieved the real sense for making the big buck but instead he was a pure strong-arm guy and professional killer and logistician. The problem was that McGurn was completely destroyed by the media and press after the infamous St. Valentines Day Massacre since every possible newspaper man around the country connected McGurn’s name to the whole situation but that’s not the point of this story. The main point is that McGurn had the investigators all over him all day long, since at the time they mainly relayed on information from the newspapers. In plane words, this completely destroyed McGurn’s ambitious criminal career and placed him in a position, similar to a soldier for some of the non-Italian big shots such as Willie Heeney and Claude Maddox, who by now were part from the Cicero crew under Ralph Capone. According to some reports, Heeney placed McGurn as one of his operators around the South Side to mingle with the African-American population regarding the numbers and narcotics rackets. Obviously Heeney had some “soft spot” for McGurn since he really gave him two of the most future lucrative operations, but story goes that McGurn was a degenerate gambler and lost a lot of cash and owed money and top of that, he allegedly consumed drugs which was a huge “no, no” regarding the Outfit’s membership, no matter if that same individual was shelved or ousted from the Mob, since in reality a member always stays a member. As I already stated that some reports say that McGurn was completely ousted from the Mob and was left on his own but no matter what was the truth, in 1936, the boys decided to end the problem once and for all.


So as I previously stated that even though McGurn looked like a bum, still he had the skills for murder or retaliation. One time he even admitted to the reporters that if he was really involved in some current kidnapping which occurred during that same time, he would’ve collected the cash in a matter of few hours. This time the hit team had less chances in killing McGurn from a long distance or from a drive-by shooting, since he always packed a couple of revolvers and was known fast shooter. So the boys devised a plan by previously relaxing McGurn and then to suddenly confuse him with a diversion so he would loose his guard and the killers could finish their job. On February 15, 1936, McGurn made a deal with Claude Maddox and William White to go bowling, have a few drinks and spend some good time. “Coincidentally” it was the evening right before St. Valentine’s Day, or in other words the massacre’s seventh anniversary, which possibly was the main reason for their gathering. The boys went bowling at the second floor of the Avenue Recreation Rooms on 805 North Milwaukee Av, which was owned by one Outfit member or possibly associate at the time known as Willie “Smokes” Aloisio. The three men entered the bowling alley and began having good time, and McGurn became relaxed like never before. According to witnesses, 15 or 20 minutes later three men with bandanas on their faces walked in and yelled “Stick ’em up!” like it was a robbery. One of the three men fired a warning shot in ceiling and everyone in the establishment has hit the floor. During the whole confusion, one of McGurn’s bowling buddies approached him and whispered “This is for you, you son of a bitch!” and than shot McGurn behind his right ear. McGurn fell to the ground and the assassin fired few more shots. The three stick up men fled the scene while White and Maddox, before leaving, one of them turned around and walked back to the table where McGurn had been sitting and took the tally sheet which had their names on it, shoved it in his pocket and walked away. Years later an FBI wiretap confirmed Maddox’s and White’s involvement in the hit.



6. As it was already mentioned in one of the previous examples that some of the non-Italian gangsters understood the real nature of the Mafia and few of those guys even managed to bring themselves into actual membership into the Capone Mob, not Cosa Nostra, but instead they were like barons who controlled parts of the city of Chicago for the Mob. We already heard regarding faces such as Humphreys, Maddox or Heeney but there were also some other quite violent and powerful racketeers such as the infamous Danny Stanton. This guy was a real hot head and started to muscle in on every possible union in the Chicago area for the Mob and became a real lucrative connection. He was one of those fellas who mingled with allies or members from the Capone gang since the days of Prohibition and according to some reports Stanton enjoyed many years of wealth from his close connections to the Outfit and entered the 1940’s as one of the prime racketeers in the union business. Story goes that Stanton’s prime “fuel” for his racketeering skills were his ruthless tactics but above all, his endless greed which made him even more ruthless in the eyes of the victims. It was ok until he kept his violent tactics only for his victims who did not belong to the Mob, but it became a huge problem when Stanton started using those same tactics on some of his peers in the Chicago Outfit. You see, general knowledge is that in 1943, the Outfit’s top leadership was imprisoned because of the infamous Hollywood extortion scandal and so it was “natural” for some of the powerful and above all, most greedy racketeers to try and take over some of the rackets. So blinded by his own greed, Stanton started making problems for the Outfit in general, like for example quarrelling with Claude Maddox over the Restaurant and Bartenders union scheme because he wanted a bigger share and he also started to muscle in on another prominent racket and that’s was the numbers scheme which by now was controlled by Sam “Golf Bag” Hunt. So obviously Stanton figured out that with the big shots already going away for good, his chance to climb to the top was now or never. But like most “rebels” from that decade, Stanton also became a marked man by some of the Outfit’s deadliest hit teams.


In this next example, or at number six, we are going to see a victim who represents an armed and extremely dangerous individual, who’s active on the streets and spills other people’s blood on daily basis and is always prepared for action. Since he was quite aware of his numerous enemies, Stanton was known for always keeping two revolvers on him, while being in the constant company of one his associates known as Louis Dorman, who in turn was also armed. On top of that, in a true gangster style, when Stanton visited some of the local joints for a drink, he usually sat with his back against the wall and his face and hands towards the door. That same situation occurred on May 5, 1943, just before midnight, when Stanton and Dorman were having drinks in a bar at 6500 May Street, while being seated with their faces towards the entering door. So that same night, the hit team which included one Outfit killer known as William Block and another unknown individual, probably Lenny Patrick or Dave Yaras, circled on foot around the bar so they can see the exact location of their target and to devise a plan right there on the spot. It was a quite difficult situation since as I already stated that both targets were armed with their faces towards the entering door but the assassins noticed one “small” detail. The thing was that there was no empty wall behind Stanton’s back, but instead there was some kind of small backdoor which also led into the bar. Suddenly the two assassins kicked the whole backdoor, including small parts from the side walls, and immediately blasted three shots with their shotguns. Dorman got one in the back and Stanton also got one but in the back of his head. After the shooting the killers ran back out and made their way to the front door and fired three more shots from a revolver through the glass panels of the front door before making their getaway. Stanton and Dorman both lay dead on the floor which obviously represented their end. The “venture” continued when one young beautiful blonde by the name of Cecelia Ashley became one of the witnesses who was sitting next to the dead gangsters and saw the killers’ faces. Her friends allegedly advised her about going to the police but still she decided to go for it, and so on May 8, that same year, Miss Ashley was walking down to the Englewood Police Station but never managed to reach the place because she disappeared from the face of the earth. Later from various sources the cops were seeking for Claude Maddox and Sam Hunt in connection with the double murder and the missing woman. They were both arrested and questioned about the killings but as usual everything ended with no results. For me personally this was one of the most professional contract killings, since the victim somehow “barricaded” himself in a small bar together with his bodyguard, both armed to the teeth, while being faced at the only entering door, or at least that’s what they thought. It was a dangerous situation in which the assassins had to find another way to get in and finish their job. I mean it wasn’t in open space or from a second floor apartment while overlooking a whole street, but instead it was a face to face situation in which the assassins came out to be more focused and killed their targets from the back and in the end fired few shots in empty space as a warning so no one would follow them.


5. Under number five we’re going to see one less professional contract murder, but the main reason for that was the power and strength which some of the hit squads felt at the time. During the mid 1940’s, the Chicago Outfit was still unstable because of the imprisoned top leadership but this was all regarding their hierarchy, meaning the rackets were still there and murders continued with even faster flow. Besides murdering their associates and members, the Outfit was also known for killing even more sophisticated targets such as cops and politicians. So if a guy kills some high profile politician and got away clean, I believe that same fella had no problem in killing a boss for example, and during the process, to make a whole circle around the block and to return to see if he has finished the job. Yes, that kind of hit occurred in 1944, when another Outfit big shot decided that he deserved more power rather than the limit which was already given to him. The individual for which I’m talking about was known as Lawrence “Dago” Mangano, an old time Mafioso, one time Public Enemy #1, and also known around the city of Chicago as the “King of the West Side”, since he literally controlled a large territory because most of the imprisoned top leaders also came from that same area. It was the same time period, when the Outfit’s acting top leadership, which did not include Mangano, was having problems with one faction from the North Side and Northwest areas. And so story goes that in the same style of the late Danny Stanton, old man Mangano allegedly decided to force and also show his superior authority over some of the younger and up and coming members such Tony Accardo. You see, at the same time Accardo was allegedly groomed for the chief executive position by the acting top leadership which included Charles Fischetti, Tony Capezio, Murray Humphreys and Jake Guzik. So if Mangano had a problem with Accardos position, he had to take it to the previously mentioned fellas and maybe really he did, but obviously he was rejected since one day he decided to hijack some of Accardo’s illegal operations, which in fact became his instant death sentence.


As I previously stated that during this period Mangano might’ve been one of the most powerful and at the same time, dangerous members of the Chicago Outfit, which in fact was the main reason for which he freely moved around Chicago with only one bodyguard who in turn wasn’t a real ruthless killer at all. There’s often one point in the life time of one high level mobster, when he feels invincible and untouchable out of obvious reasons, but that’s also the same moment when they make their fatal mistake. One night on August 3, 1944, Mangano together with his friend and bodyguard Michael “Big Mike” Pontillo and a young girl named Rita Reyes, visited a bar in Cicero named the Paddock Lounge for relaxation and a couple of drinks. After more than a few drinks, at 4:00 am they left the club, climbed into Mangano's shiny maroon 1941 Mercury and headed home. Now this is one proof that Mangano felt completely comfortable in Chicago’s underworld since he the one who was behind the wheel driving along Blue Island Avenue on the West Side, while his companions were having a drunken conversation. Now this is the only moment where we can witness a pure professionalism by the murder squad, since they could’ve not picked a more perfect time and situation rather than this one for executing their main target. Suddenly old man Mangano spotted a black sedan following them, and at first he thought that these were cops and so he stopped the car and got out to talk to them, which is the second proof that Mangano looked himself as the top guy in Chicago’s underworld and no one dared to touch him. But as the black sedan rolled towards him, it suddenly stopped and one gunman pulled a shotgun and blasted at Mangano while fatally hitting him in the chest. Mangano fell in the street as the sedan raced away, screeched around a corner and was gone. Pontillo and Reyes got out of the car and managed to drag Mangano to the sidewalk. Mangano was somehow barely alive and now this is the right moment in which we can see the real ruthlessness by the assassins, which is a pure sign for the Outfit’s power on the streets at the time. The killers made one quite arrogant move by making one huge circle around the whole block and went for a second attack. This time Pontillo saw them and pushed Reyes down to safety, while hundreds of shotgun pellets went through his flesh and fell right beside Mangano, who was behind their car. Now if you look at the situation more clearly, the assassins gave their target a mortal shotgun wound from a very close range and that should’ve been enough for the day. On top of that, with the help of his bodyguard, the target was dragged behind their car out of the assassins’ reach, and while all of the police sirens were closing down on the scene, the hit squad decided to make one whole circle around the block and finish off the bodyguard and girl. Luckily the girl remained unharmed. So with over 200 shotgun pellets in his body, Mangano managed to remain alive for at least an hour and when the cops asked the old timer on who shot him, he replied “If I knew I’d tell you”, and so he was quickly rushed to the hospital where he screamed in pain and begged the doctors to put him to sleep. He died at 5:48 a.m. and Pontillo followed him in death five hours later. Questioned about the Mangano murder were Dominic Nuccio, Dominick DiBella and Dominic Brancato, the main suspects who were known as the main hit squad for the Outfit at the time. There were only family relatives at Mangano’s funeral who embraced each other tearfully, since none of his Mob associates and alleged friends showed up which shows it was a pure sign of disrespect and that he was ousted from their organization.

4. Next example on this so-called “top ten hit list” is another high profile Chicago mobster whose situation was somehow connected to the previous two examples. I mean it occurred during the same decade which was the 1940’s, when, as I already stated, many members and enemies felt that the organization was quite vulnerable and was exposed to the possibility of being taken over by more powerful factions. But obviously they all thought wrong since many of the evidences point out that the boys held their ground strong with killing many people during the process. During that same troubled decade, the old North Side Mafia was already in alliance with the Capone Mob and they all formed the Chicago Outfit. But during my long time research, I managed to notice that even though they were considered a part of the Outfit, still the so-called Northsiders were always overseen by former high profile Capone members, as if they watched for any possible rebellion. And to tell you the truth they were right. You see, the main boss or captain of the huge North Side area for the Outfit was one James DeGeorge, but two parts of his territory went to the former Capone big shots the Fischetti brothers and Frank Nitto. So according to numerous reports, DeGeorge was very loyal to the Outfit’s top administration but the main problem was his own crew wasn’t at all. Some of his crew members decided to use the same situation, or in other words, to make the same mistake as the late Lawrence Mangano or Danny Stanton. In fact, this was the crew which got the “best” of it, meaning many of their members ended up dead on the city’s streets but one contract murder stood out of them all. You see, one Vincent Benevento was the second in command under DeGeorge, with operations all around the North Side but mainly on West Grand Av., near Elmwood Park, which in fact was Accardo’s territory. Since the days of Prohibition, many former North Side Mafiosi tried to expand their rackets to the Northwest and further to the Near West Side, which always represented the main problem and conflict between them and the criminal clans who were already settled in those areas. After Prohibition or when the Outfit became complete, which included Capone’s old territories and also the whole North Side, still through the decades there was allegedly some hidden dissatisfaction from some of the old North Side Mafiosi towards the Outfit’s top administration which was mainly controlled by long-time Capone members and allies.


So the so-called cleanup of the North Side crew began in 1943 and by 1945, most of the members were running for their lives, except for Benevento who had similar way of stubborn thinking like the late Mangano, and decided to stay armed and refused to run. Since he was an easy target, meaning he had no bodyguards or any kind of armed company around him, the boys decided to pull off a simple job by shooting him and to manipulate the situation so it can look like a robbery. So on December 28, 1945, Benevento was working in one of his cheese stores at 1057 Grand Avenue, when suddenly three gunmen with bandanas on their faces entered the store and ordered Benevento to raise his hands. The stubborn old timer obviously refused and one of the gunmen simply fired four times from an automatic pistol at the victim. When the smoke cleared, Benevento was hit twice in the stomach, once in the neck, and once in his left armpit but miraculously he somehow managed to survive the attack. When the cops searched his apartment they found a huge arsenal of weapons, including a Thompson submachine gun, eight shotguns, six rifles, eight revolvers, two pistols and a basket full of ammunition. All of the weapons were loaded and well oiled, which means that he was prepared to defend himself from the wrath of the Outfit. This obviously a botched hit which was possibly executed by less skilful assassins or maybe Benevento was too lucky. No matter what was the real reason behind his survival, still the job had to be finished or some else was going to get hurt, meaning individuals from the hit squads. Now the main thing which managed somehow to fascinate me was the constant search for their target for almsot seven months, since on March 1, 1946, Benevento was out of custody and hospital care and so he informed his wife that he’s heading south and fled Chicago and travelled around the country constantly. So I don’t know if they somehow tapped his family’s phone or maybe he was betrayed by his own wife, since on September 20, 1946, Benevento called his wife Jane and told her to meet him at the Johnson Cabins, about three miles south of Lake Zurich, under a different name. In the early hours of September 21, Benevento and his wife were sleeping in their cabin when suddenly out of nowhere two cars filled with assassins came near the place. Only three hit men came out of the cars and came nearby, when they quickly burst open the cabin door and fired almost a dozen shotgun blasts and dozens of .45 caliber pistol bullets at Benevento, whose body was riddled by the blasts and so were the mattress beneath him and the even the wall behind the bed was penetrated since some of trees behind the cabin were also damaged. The main miracle was that Benevento’s wife was lying right next to her husband but somehow remained untouched by the hale of bullets which occurred in a tiny wooden and bullet-riddled cabin. As I already stated that I have no idea on how did they found out about his true location, but I know for sure that the assassins had one main job which was to make sure this time that Benevento was dead for sure, in which they obviously succeeded above all with the help of betrayal.


3. Besides killing each other all over town and around the country, and no matter if there was war on the streets, still the old timers continued to expand their rackets and got involved in various new ventures which brought additional millions of dollars into their “cash register”. But sometimes they were “forced” to wash their hands in blood if some of the victims refused to include them in those same ventures. The thing was that many powerful businessmen at the time were becoming quite aware of the Mob and their extortion methods, and so they decided to protect themselves and to say “No” to the racketeers. Obviously for someone to make such a move, he or she had to be foolishly brave and to have some previous violent experience so the individual can mentally handle the dangerous situation which is about to consume his whole life. During this period one of those types of tough individuals was James Ragen, a very well known Chicago-born Irishman, who with the help of his short temper and business skills managed to “fight” his way up to the top of the racing wire service which connected all of the cities around the Midwest. Now that was Ragen’s “golden goose” which in fact was named the Continental Press, and serviced thousands of bookies between Chicago and Los Angeles and made millions of dollars, since this type of wire service was very important for the bookmakers at the time to manage their business because each bookie had to have fast, up to the minute information on the horse races running all across the country. You see, back in the 1930’s, Regan joined one gambling magnate known as Moe Annenberg and began working on a nationwide racing wire service from Chicago to St. Louis. So I don’t know if Ragen forgot or simply played dumb, but the roots of this operation were created by the old time Irish crime syndicates, which means that organized crime was present at any time. So at the beginning of 1946, Ragen was allegedly personally approached several times by Tony Accardo, Murray Humphreys and Jake Guzik., who in turn later also sent death threats to his house and work office. The Mob bosses even managed to set up a rival service called the Trans-American Wire Service, and so each Mob boss from around the Midwest had to take their services so they can take Ragen out of the business. Ragen was a very stubborn person and he didn’t back off and the problem was that in reality he was scared and made a fatal mistake by trying to make a deal through U.S. Attorney Tom Clark to provide information to the FBI on the bookmaking industry in return for protection, but the shady director of the FBI at the time J. Edgar Hoover turned down the offer and Ragen quickly became a marked man.


From April, 1946, James Ragen began carrying a revolver on daily basis and hired two highly professional and armed bodyguards to follow him during his daily routines. Ragen was usually riding in his car alone with his pistol on the side and was closely followed by his two armed bodyguards in a separate automobile, which in fact is a known tactic for protection, meaning if somebody attacked Ragen’s car, the bodyguards would simply hit the car or individual and start shooting and make it impossible for the attackers to finish their job, since by that time Ragen will be away from the scene. But as I previously explained that the main problem was that during this particular decade, the so-called murder tactics of the Outfit became more sophisticated, since obviously the 1940’s was one of the most murderous decades in the Outfit’s history and many of the assassins had the opportunity to improve their murdering skills. For example, some of the hit squads were known for using so-called hit-mobiles which often were same types of a dark coloured sedan designed for committing murders. For example, the car had three hidden switches under the dashboard and two of the switches disabled the taillights so it will make the car harder for tracking at night and the third switch opened hidden compartments that often held a scary collection of weapons and torture tools. One of the first infamous hit squads of that type at the time was the deadly duo which included Sam “Teets” Battaglia and Marshal Caifano. One day the cops searched their car and found a whole arsenal of hidden weapons such as sawed off shotgun, a rifle, a hand grenade and five pistols. Later another infamous duo used the same tactic such as the deadly relationship between Phil Alderisio and Charles Nicoletti. But according to some reports, in Ragen’s case the Outfit decided to use another type of deadlier tactic which was about too finish the job 100%. You see,


This time Tony Accardo called for one Jewish hit squad which recently became the Outfit’s ally, since they received a part from the late Mangano’s territory and possibly were involved in his betrayal. The group was headed by three Jewish gangsters including the already mentioned William Block who was involved the Stanton murder and his everyday cohorts Lenny Patrick and Dave Yaras. These guys were different than the Italian hit squads since they previously fully prepared for the job in their own way. For example, since the so-called Ragen group was moving in two separate cars and they were all armed, the boys decided to use a delivery truck and they covered the whole thing with quarter inch steel plates, just to make it bullet-proof since they expected a quick retaliation from Ragen’s bodyguards and maybe even Ragen himself if they somehow miss their target. On one of the sides the truck had tarpaulin which can be easily lifted before the shooting occurred, and after finishing the job, the boys had to close down the door with one huge bullet-proof steel plate. So the stage was set and on June 24, 1946 the trio got into the truck and began following Ragen from his home down along State Street. At the corner of 39th and State Street Ragen stopped and waited for the green light, while closely being followed by his two bodyguards. Lenny Patrick was driving the truck and pulled to the right side of Ragen’s auto and as the target waited for the light to change, the tarpaulin on the left side of the delivery truck was pulled up and William Block and Dave Yaras pulled off their shotguns and aimed at Ragen’s vehicle. Two blasts were fired and one of them almost completely tore off Ragen’s right arm from his shoulder. The two bodyguards quickly jumped from their automobile and returned fire but the truck already sped away in a matter of seconds. Ragen was barely alive and was rushed to the nearest hospital. He was in critical condition but the tough Irishman remained alive until August 14, meaning over a month, when he died under mysterious conditions. It was later reported that Ragen’s autopsy showed traces of mercury in his blood and abdomen indicating that someone had entered his room and poisoned him. Two weeks later, two unknown figures with diamond rings and gold teeth, tried to snatch Ragen’s body from the cemetery vault. They told the lady who worked there that they are seeking the key from the vault and also offered her money. She refused and told them to come back later so her husband can give them the key from the vault. The two unknown persons disappeared and the lady became suspicious and notified the police. The apparent attempt to steal Ragen’s body was made to thwart the poison investigation because the chemists began tests to determine whether there was enough mercury in Ragen’s vital organs to cause death. Either way the Outfit won the war and again showed their ability in eliminating anyone at anytime and at anyplace.


2. To tell you the truth, there’s really nothing special regarding this particular contract killing except excellent marksmanship during fast speed or during a drive-by shooting and the fact that this type of murder will be often seen during the next decades especially during the 1960’s, 70’s and onward. The main reason for that is the fact that is quite faster, cleaner and did not require many special skills, except for knowing how to shoot while being in movement. Also the types of weapons which were used during these types of hits also changed, meaning some of the hit men began using more sophisticated weapons rather than Tommy guns which can easily hurt some innocent pedestrians. You see, 1950’s was the golden era for the Chicago Outfit and the syndicate largely expanded their operations but above all their membership and the reason for this was simple, meaning the younger and hungrier generations were taking over and the number of skilled individuals in the sphere of murder was getting bigger and bigger. On top of that, during this same period Chicago’s faction of America’s Cosa Nostra was slowly becoming one of the most powerful national Mafia clans and so they did not battle only on their own territory, but instead they killed people all around the country. They also stopped killing their bosses and completely changed their ways and tactics when a murder was ordered. I mean they still kidnapped people off the streets and tortured them in basements for several days and later threw their dead bodies in sewers and garbage dumps. The cops still found garrotted victims or simply shot to death and placed in car trunks, which two decades later or during the 1970’s became the main murder fashion among the Outfit’s ranks and was also known as “trunk music”. Even though the new and up and coming bosses wanted their problems to go away on a more quiet style, such as the previous ones, still when somebody was needed to be made an example, bombs and drive-bys were the main answer to some of their problems.


For example, during the mid 1950’s more than few hits occurred on some of the Outfit’s high profile members but none of them were sensational, like the 1954 murder of Charlie Gioe, who after dinner at some restaurant, the target and his companion entered their car at the parking lot, when a black car approached them and two hit men opened fire from two pistols, while hitting Gioe in the head and instantly killing him. Also the 1955 murder of Alex Louis Greenberg almost went wrong since while the old man was leaving some restaurant in the company of his family, out of nowhere he was shot possibly by the same two hit men who were previously involved in the Gioe hit, but surprisingly Greenberg turned out to be a tough guy and so while being shot, still he somehow staggered after the men as they fled on foot and almost hit them. Greenberg collapsed about 12 feet of the curb and the killers were never caught. Maybe the so-called loudest murder which occurred during that decade was the contract on one former Outfit associate and extortionist later turned informer named Willie Bioff who changed his surname into Nelson, which was his wife's maiden name, and relocated to Tucson, Arizona; out of obvious reasons. So on November 4, 1955, many people were stressed to the bone when Bioff got blown to pieces in his automobile, which sent shock waves around the whole area, personal “regards” from Paul Ricca and the boys. But for me personally there was one murder contract which occurred a year earlier from the Bioff hit, which I personally noticed some real professionalism which again strangely managed to fascinate me and made me place it on the number two position. You see, as I already stated that during this decade the Outfit was at the top of the criminal food chain in the U.S. and beneath all of those numerous rackets and schemes, under all of that huge pile of lucrative operations, the highly “sensitive” narcotics business was deeply buried and silently filled the bosses’ pockets with additional cash. The racket wasn’t their prime money source but still it was under strong control by the top hierarchy and the main rule was “deal but don’t get caught, because if caught, you’re going get whacked”. So Tony Accardo’s and Sam Giancana’s hit teams were quite busy during this period and somewhere among those dozens of killings, one hit squad managed to pull off an “amazing” job for their bosses. During the early 1950’s, both Accardo and Giancana controlled the Outfit with Ricca at the top or in the shadows and as I already stated they controlled various rackets, including dope peddling. So one of those so-called Outfit “junk crews” was headed by one Mob associate known as Anthony Pape, who in turn was an individual with blood relations to some criminal old timers from the Chicago area such as former members of the old 42 gang and above all, he possessed extraordinary skills regarding the counterfeit business.


Tony Pape was also involved in other schemes such as the lucrative auto-theft racket which additionally tripled his underworld connections and made him the right guy for the likes of the Outfit’s top hierarchy. He was also the right guy for the dope racket since the operation required a large number of people so the product can be quickly and easily spread around Chicago’s city streets, and Pape knew a lot of street level or low level criminals. This is not the point in this example, but I only wanted to capture the picture for you regarding Pape’s lucrative status in the eyes of the Outfit’s top brass since he really managed to screw things up when on March 16 and 17, 1954, FBN agents arrested eleven members on narcotics charges, including Pape and quickly took them into custody. Now, the main problem was that three of the defendants had direct contacts, not only with some members of the Outfit, but also with some of the top level guys such as Accardo and Giancana, and the main guy from those three defendants was Tony Pape. That’s when the bosses quickly disconnected themselves from the operation by giving the thumbs down. Immediately, “somebody” posted the $25,000 bonds for all defendants and they were released and the trial was set for April 22, 1954. On the day of their release, April 10, 1954, Tony Pape together with his brother James got into their car and drove home. While driving down Flournoy Street, suddenly another car with two masked men tried to block their path and James Pape, who drove the car, quickly made a wild effort to elude the hit squad by turning his car around. The car chase lasted for more than a mile, since the Pape brothers were also known for fast driving and getaway operations but the hit squad somehow managed to get near their targets. Now this is one the most “fascinating” moments and that’s when one of the assassins, in a matter of seconds, managed to fire only two shotgun blasts, thus fatally hitting James in the head and also fatally wounding his brother Tony also in the head. Suddenly their car went out of control, struck the corner of a building and crashed on the sidewalk. James’ body was found sprawled face down in mud with his brain missing and with his legs still under the steering wheel, while Tony was quickly taken to the Garfield Park hospital in a critical condition and possibly in coma and died two days later. My obvious point is that the skilful assassin somehow managed to pull off two almost impossible headshots with a shotgun, in a couple of seconds, during a high speed chase on broad daylight. I really don’t have a clue on who actually executed the Pape job but whoever it was he surely did one helluva murderous job. I mean the assassins were not stuck in one place so they can take their time and hit their targets from a close range, nor they used some kind of machinegun like AK-47 or Kalashnikov from far range or in this example, during a car chase which is the most “preferable” weapon in a situation such as that one, by simply spraying hundreds of bullets in few seconds, thus eliminating everything that moves.


1. So finally we came to the last example or my personal pick regarding the number one spot for the Outfit’s so-called greatest hit list, and possibly even the Mob’s list in general, which goes to the fella or fellas who orchestrated and executed the 1975 “Machiavellian” contract killing of Sam Giancana, one time and also most infamous boss of the Chicago Outfit. For me personally this was the most original and cunning murder contract which ever occurred during the Outfit’s history, out of various reasons. For example, as Mob history taught us that one of those reasons was for Giancana becoming the chief executive for the so-called Chicago Mafia at the most possible wrong time mainly because during the late 1950’s, the feds already started their secret surveillance program and the Outfit was their prime target. But even with that, somehow Giancana managed to stay at the top for 8 whole years until 1966 when he went out of the country to further spread the syndicate’s international operations. Even though he was mostly out of the country, still the media and the government never really stopped “harassing” him, which means Giancana managed to reach higher level of popularity rather than his predecessor the infamous Al Capone. Things went “smooth” until July, 1974, when the government of Mexico decided to expel the Giancana from the country straight to the U.S. within 24 hours. The strange thing was that neither the U.S. Embassy nor anyone from the government at the time did not gave any specific explanation regarding Giancana’s deportation since there was no kind of official indictment, nor any kind of strong evidence that at the time he was involved in any illegal activities, meaning no matter if he really was since he was “clean”. The only explanation was given by the by the Mexican authorities who in turn reported that it was “just an internal decision” to expel the “unwanted alien”, who was living illegally in their country. Now, according to many investigations, Giancana had a lot of property around Mexico but the thing was that he rarely stayed there since he was constantly travelling around South America, to Canada, around Europe and Africa. On top of that there were many speculations that Giancana took a lot of money with him, which can obviously explain his real estate around Mexico and different countries, and story goes that he literally bought many Mexican government officials, which is something that every Mafia boss would do while staying in a different country and I hardly doubt that during those days most of the highest Mexican officials weren’t corrupt, since their “product” are today’s most dangerous drug cartels.


Well this is how I believe they began to carryout the contract killing on the old boss…you see, before getting out of the states, Giancana personally oversaw a huge and quite lucrative international operation, which included few of the Outfit’s most lucrative and at the same time, elusive members such as Eddie Vogel, Gus Alex, Richard Cain, Hyman Larner and many more and these particular guys had obviously higher ranks. So this so-called overseas group was dubbed by the feds as the “Combine”, which obviously later became Giancana’s only ticket to be simply not around, meaning in the Chicago area. The problems started during the late 1960’s when Cain went to jail and Larner took over his position, while Alex was appointed for Chicago. Cain was killed in 1973 since he was ousted from the business and allegedly informed on some local gang. So when Larner took over, story goes that the Outfit ordered him to slowly cut loose Giancana from every international operation, and that’s what Larner really did. So without his main money source, Giancana slowly began to sell some of his real estate around the world and during the first half of 1974, he almost completely lost his cash. How that really happened, it is very unclear to me. I mean surely the selling of most of his real estate would’ve cost a couple of million dollars at least which means would’ve bought him additional 3 or 4 years, give or take. Although we cannot say anything about Giancana’s lifestyle at the time, since we all know that during his criminal career, he always spent his cash lavishly, which means if he continued that kind of life style, there’s a great possibility that he managed to spend that kind of cash for even shorter time period. My point is that if he managed to spend the money, than there’s a great possibility that the corrupt Mexican officials dried him out of his finances and betrayed him. But the problem is that I personally doubt that if Giancana was aware that his finances were coming to an end that he would’ve still stayed in one place and wait for them to deport him, which is obviously pure nonsense. So I believe that yes they obviously betrayed him but not because for his alleged zero finances but instead it was someone from the American side who really must’ve pulled some strings in the highest circles of the Mexican government for that kind of betrayal to be executed, meaning to deport someone who regularly fills your pockets with cash. So story goes that besides deporting him, those same Mexican authorities also confiscated or seized Giancana’s remaining real estate and they even placed their hands on some of his hidden cash, which I believe was the main reason for his fast and complete economic downfall. In plane words, Giancana was robbed and kidnapped during night time from his sanctuary, and with the speed of light, he was deported to the U.S. in his pyjamas and slippers. I mean yeah, he obviously had secret bank accounts but usually the gangsters’ prime stash or getaway cash for “rainy days” is always nearby.


So while being back home, the government did not miss a chance to question the former Mob boss with the help of grand juries, mainly regarding his past CIA connections and activities and also regarding his illegal activities post the year of 1966, or after his alleged self-imposed exile. You see, the government knew that Giancana was an “old book” full of Mob secrets regarding America’s Cosa Nostra in general, but the main reason was that Giancana also knew a lot of government secrets which could’ve destroyed any past or current government administration, if they got out. And if that ever happened, there goes the Mob’s protection and main “shield” from honest investigators. And as it was already expected, their “safety” became quite disturbed when in January, 1975, Giancana agreed to appear before a federal grand jury in return for the feds to stop their close surveillance on the former boss, which was all granted. Now this was the kind of problem which made a lot of Mob-connected people worried, such as politicians and businessmen, regarding their own safety and lucrative positions. You see, a lot of people knew that Giancana was tired from all those “Gestapo” tactics and on top of that he began having serious health problems, which meant that he wasn’t ready for another jail term. On top of that, some rumours spread that Giancana was ready to talk and implicate many government individuals for which he held a lot of old grudge. So my personal belief is that there was pressure over some Outfit people from government individuals or in plane words, it wasn’t direct fault or there wasn’t direct involvement by some of corrupt officials from the government, but still there was some kind of indirect involvement and fault by those same people in wanting or placing pressure for Giancana to be removed from the whole picture. So now we can slowly unravel the real villains or logisticians behind Giancana’s demise, which I personally believe were his old buddies from the so-called “Combine”. I’m not talking about Ed Vogel who was retired by now and lived like a Pharaoh, but instead I’m talking about Gus Alex, the Outfit’s main corruptor and financial schemer who one the time was the main individual between the Mob in Chicago and the corrupt government, but later became some sort of adviser and mediator with more power than some of the high level Italian members. So if you really think about it, Alex was the guy who succeeded the late Murray Humphreys as top non-Italian boss, Alex was the guy who was seen having heated conversation with Richard Cain before being killed like a dog, and Alex was the guy who supervised Hy Larner’s overseas activities. On top of that, Hy Larner who was the “second in command” regarding the Outfit’s overseas schemes, especially around Central and South America, I personally believe that he never really relinquished his CIA contacts since he was quite valuable individual for the secret agency mainly because his close contact with high level individuals from various countries. You see, Larner was previously in a similar situation like Giancana, meaning it was too hot for him to stay in his home country and so he fled to Panama, but obviously the underling managed to stay longer in those same waters rather than his mentor and former boss and continued to be valuable in the eyes of the secret government. So my point is that these two guys, meaning Alex and Larner, had too many high level government connections which were quite valuable for the Outfit and also their own positions and safety within the organization, or in plane words they were the ones who possibly brought the problem in front of the Outfit’s top bosses. In addition, Alex was actually one of the three top bosses until 1975.


The main problem for Giancana was that he was a very disrespectful person and was known for holding grudges during his whole life time. You see, in May, 1975, one of the world’s most famous and at the same time Mob-connected singers like Frank Sinatra arranged for a secretive party for his “Chicago Italian friends” and according to some FBI records, Outfit members such as Dominic Blasi were personally contacted by the singer and especially invited to be present, but Giancana refused since he and Sinatra had some conflict during the early 1960’s. So my point is that Giancana made a mistake by disrespecting his old peers, instead of accepting the situation as it was and pay his debt to the government and possibly die in prison. If you really think about it, this same situation occurred several decades earlier when Frank Nitto took his own life just to avoid prison sentence and answering questions in front of grand juries, since he was labelled by the media as Al Capone’s successor. So Giancana obviously refused to do that, meaning going to prison or taking his own life and that was the final decision for the Outfit’s top brass to order the contract killing. Now, by looking at Giancana’s situation at the time, I believe that it was easier to kill the president of the United States rather than the retired Mob boss, since he, meaning Giancana, had more media and federal coverage than any other high level government official. Even though he was previously granted for the feds to stop following his every step, still his house was on constant surveillance from a close distance and the newspaper men followed him every where he went. So if someone wanted to get near Giancana and to execute the job, he or she had to be his loyal and trusted companion, and the Mafia was excellent in providing that kind people or forcing them to make such a move. According to numerous FBI reports, Giancana’s closest people at the time where obviously his family members, his caretaker and his family, but also two of his old confidants such as Charles Inglesia a.k.a. English and Dominic Blasi. These fellas were always direct with him when he was the boss of the Outfit and allegedly remained like that even during his stay out of the country, but I personally believe that their main job was to closely watch the former boss and report back to their current top administration, which was Tony Accardo, Joey Aiuppa, Jack Cerone and Gus Alex. So English was the guy who rarely but still visited Giancana from time to time, but Blasi was the guy who more often visited his former boss. Now according to Giancana’s caretaker, both fellas were instructed by their former boss to visit him during day time so the feds can notice them and that nothing was really going on, but if they wanted to talk business, during night time Giancana would’ve slipped through the back door of his basement kitchen and go wherever he wished to. Giancana’s caretaker also stated his boss owed him money for seven months and one time when he asked about it, which was one day before Giancana’s demise or June 18, 1975, the old boss assured him that he was going to have the money in few days and that he was going to get much more than that. So obviously someone was filling Giancana’s mind with wishful thoughts, and I believe that individual was Blasi. You see, Giancana just returned from a serious operation and so he couldn’t move much, which allegedly was the main reason for Blasi’s one time night visit at 11 PM on June 19, 1975. Obviously Blasi was the “chosen one” since after arriving, he immediately ordered for Giancana’s caretaker to bring him a bottle of scotch, which was something rare for Blasi to make in Giancana’s house and means that something was bothering him and he needed to calm his nerves, since it wasn’t easy for him to kill his old boss, but above all, his old friend. And as for Giancana, it was his second day out of hospital and on top of that, he was getting old and possibly failed to recognize the signs. According to the caretaker, Blasi began drinking and didn’t say a word, while he and Giancana were looking at some broken water pipe. After that, or at 11:20 PM, the caretaker went upstairs and left the two men to talk and after watching TV for almost an hour, the caretaker looked from his window and noticed that Blasi’s car was gone from the driveway which meant that he took off. So the caretaker decided to visit his boss downstairs and when he opened the kitchen door, he was stunned by the situation since Giancana was lying on the floor with his face up and a huge pool of blood under his head and neck.


At first the investigators found six .22 caliber pistol casings and later a seventh one, which means that Giancana was shot one time at the back of his right ear, which was the shot that brought him down on the ground and possibly killed him, but his assassin had to make sure that the old boss was dead by placing the gun in the area under the chin and close to the neck and fired six more rounds. Many people say that the six shots were in fact a Mafia “message” but that’s completely false since that’s the area where the bullets can easily penetrate the skull and enter the brain. Whoever did the job had to make sure that the boss was dead but the confusing thing was that Giancana’s wallet was out of his pockets and laid beside him. So we can obviously rule out that somebody went for the money since they found $1400 in his pockets, but the question remains on what was in Giancana’s wallet which made the assassin or assassins to search for. According to some of Giancana’s caretaker and also closest family friends, the late boss almost never took out his wallet in front of other people since he always carried his money in his pockets instead of his wallet which he always used only for credit cards and important paper slips. Allegedly Giancana had some paper sheet in it, possibly with some kind of unknown and dangerous information which was later missing from that same wallet. Whatever happened and whoever ordered and also executed the contract killing on Giancana, those individuals obviously had a lot of backing and experience in the job, since nobody ever saw or heard anything that night, while the whole world was watching over Giancan’s Oak Park home that same evening when the murder occurred. It was a chaotic labyrinth of corruption, betrayal and greed in which one old and stubborn boss got the “best” of it, since everyone wanted him out of the picture including the feds who were constantly being sued by him, or the CIA which had quite a troubled and expensive past with him, and in the end his peers in the Mob who had quite enough of his disrespectful behaviour and pulled off the hit of the century.

Excellent TooDoped... I like your logical argumentation... Nicely done.

Many thanks to you Jimmy and regarding my logical arguments, believe me you don't want me to go into the St. Valentine's Day Massacre or the hit on Mayor Cermak , which I truly believe that the massacre was a "joint" operation (gangsters, policemen, politicians), and the Cermak hit was a pure vendetta, also possibly backed by some rival political factions

Nice work Toodoped How about doing the serial killers of the Outfit

Well Done! How long did this take you? 2 days?

"Greatest Hits"

LOL......I have a Michael Jackson Greatest Hits CD and it don't look nothing like these.

@rickydelta thanks and believe me that would be a huge list, maybe something like top 100

@ItalianIrishMix also thanks man and to tell you the truth it actually took me three days and yeah I remember that and I also remember during the early 90's having numerous cd's named Dj Hits

Come on Toodoped Top 10 or even Top 20 and even get there Hit Rate and the hits you think they did . I am sure u can do it in a few days

Giancana got himself into an impossible situation. After he served a year in prison for contempt, he was released at the end of June 1966. U.S. Attorney Nicholas Katzenbach ordered Ed Hanrahan, et al, to stop any further subpoenas of Giancana. Hanrahan was prepared to hand Giancana another subpoena when he walked out of jail the last of June, 1966. I think we all know about Giancana's departure to Mexico and his unceremonious return. There's no doubt in my mind that pressure was on the Mexican gov't to "throw him out."

Fast forward to May 1975. Giancana had gall bladder surgery in Texas ( Dr. Michael DeBakey). Of course he didn't followed any of the hospital orders and left when he decided to leave. He returned to the hospital a little later in May with complications from his surgery. Sam Giancana was sick and very weak.

Giancana had testified four times before the Grand Jury and was scheduled for a final appearance when he was killed. Blasi appears to be the most likely suspect although there are other theories. It's not likely we will ever know who killed Giancana because all the people involved are dead. Accardo and Aiuppa had to be in on the order; and possibly Alex & Cerone. It was almost a given that Accardo & Santo Trafficante would be subpoenaed next. There were also several others who could have found themselves in front of a Congressional Committee. No doubt the Outfit leaders decided "enough is enough," so they eliminated the problem. About 13-14 months later the last threat to some of these upper echelon men, Johnny Roselli, would meet a similar fate. Oh, the Church Committee was questioning Roselli. The gov't announced there would be an investigation into the circumstances surrounding Roselli's death. No investigation was ever conducted.

I believe that the feds questioned almost every high level Outfit member and also some Mafiosi from different crime families regarding the deaths of both Giancana and Roselli and obviously nothing came out of it, and most of the guys even said that they never knew Roselli which were obviously lies. In plane words, Giancana was a guy with many secrets in his head and also with many old enemies(feds,cia agents and mobsters) which he created during his term as boss and it was only a matter of time until he made another mistake which obviously was his own demise. For example, according to some of the newest JFK files, Giancana was offered $150,000 (which is more than 1 mil in today's money) for Castro's assassination, which in fact never really occurred and I highly doubt that Giancana refused that kind of cash and swindled the agents whenever he could

Excellent as always Toodoped. I have a question about the st valentines day massacre. You said the police and govt agencies were involved how so? Ive never heard those as "co-conspirators and wondered if you could share some brief insight on that subject

Thanks AntSamuel but I didn't say gov agencies but instead I said politicians. Here's one timeline on how the massacre and some of the investigations went down, which might clear things up for you:


A meeting occurred in late October, 1928, in the Chicago Heights area, which was a place that Al Capone often used as a hide out. Capone gathered his men at the house of the new rising boss of the Chicago Heights faction, Vincenzo Ammirato a.k.a. Jim Emery. Other gangsters who attended this meeting were Frank LaPorte, second in command of Emery, Sam Costello, the boss of the Sicilian faction in the Heights, James Summons, a known murderous Capone associate, Louis Campagna, Rocco DeGrazia, and "Circus gang" leaders and associates from the North Side area Claude Maddox and Willie Heeney. There were possibly two agendas at this mob convention, one was the placement of Emery as the new acting boss of the Chicago Heights since the previous boss Dominic Roberto was having deportation problems, and the second agenda was the problem with the Northsiders and how to solve it. These are obviously only speculations because most of the men who attended this so-called Mob meeting, including Heeney, Summons, Maddox and DeGrazia, all were current enforcers and had more muscle than brains. Maybe some of these guys were only there as Capone’s personal security but coincidentally was that all of them were also good logisticians and simply there were too many of them in one place at the same time.


In late November 1928, Capone called for another meeting with the boys from out of town and this particular meeting took place at a house on Cranberry Lake, six miles north of Couderay, Wisconsin. Allegedly present at the meeting besides Capone were Frank Nitto and Louis Campagna, with Fred Burke, Gus Winkler and Fred Goetz on the opposite side of the table. Now for these types of killers and shooters to seat with the top Italian crime brass of Chicago at the time, was almost unthinkable only if there was obviously something important to be further proceeded. So here’s where the political connection comes in, meaning two other individuals who also attended the meeting were the First Ward Republican committeeman and possible Capone member Daniel Serritella and also North Side politician William Pacelli, who in turn was probably brought by Serritella regarding the police protection in his territory, which is a possible answer on why they would bring a North Side politician to this particular meeting?! This organized crime convention lasted for almost two weeks and the men were hunting, fishing while allegedly planning the elimination of the Northsiders and the logistics during the execution, obviously with the help of the so-called “out of town boys” who would all receive a $5,000 payment for the job and the task for the crooked politicians was to take care of the law during and after the hit. Also since he was America’s most famous mobster and was usually blamed for every single crime which occurred in his city, Al Capone decided that it’s better to leave town during the operation and to enjoy his summer home in Miami, Florida, which would also be his main alibi. This testimony comes from Byron Bolton who allegedly also attended the meeting but his role was to serve the big shots with drinks and prepare meals.


Now I believe that the close police connection and the ideas of using police cars and uniforms comes in early December, 1928, when one William Davern Jr was shot and killed by a member of the Moran gang during a fight in one shady hangout at the time which was known as the C&O Cabaret and Restaurant at 509 North Clark St. The biggest problem was that the late Davern was the son of a Chicago police captain and also the cousin of Capone member William “Three-Fingered Jack” White. So I personally believe that both, meaning the police captain and the ruthless gangster, were screaming for blood and were also somehow involved in the logistics of the future assassination. For example that same month, the boys bought a police Cadillac from an auto dealership on Irving Park Road and the car previously belonged to Cook County Commissioner Frank Wilson and the individual that was sent to buy the car identified himself under a different name such as “James Morton (Martin?) from Los Angeles”, which in reality was Byron Bolton. They also bought another car, Peerless Sedan, under the same false name. The plan was for Bob Carey to drive the false police car with Fred Burke and Fred Goetz dressed as cops and another gangster known as Rocco Belcastro would be driving the other car with the other two hit men, Gus Winkler and Ray Nugent, dressed as civilians.


On February 1, 1929, one member of Detroit’s Purple gang called the Northsiders and said that he had the shipment with booze ready and will deliver it on February 14, 1929, Valentine’s Day, between 10 and 11 a.m. They assured the caller that they would be there to help unload the truck in the gang’s garage on 2122 North Clark Street. It was allegedly a betrayal since after that the caller informed the Caponites that there will be a shipment of booze on Valentine’s Day at Northsiders’ hangout on N. Clark St. That’s the same moment when Byron Bolton, one Jimmy Moran and Jimmy McCryssen rented rooms along North Clark Street, across the garage which in fact was a regular hangout for the Northsiders. So Bolton and Jimmy Moran rented a room at 2119 N. Clark St. which was owned by Mrs. Michelle Doody and McCryssen accommodated himself on 2125 N. Clark St. at Mrs. Minnie Arvidson’s apartments. The three men represented themselves as cab drivers who worked the night shift and they insisted on rooms in the front, overlooking Clark Street. The three men rarely left their rooms and for the next ten days they constantly overlooked the area. Their job was allegedly to watch for Bugs Moran and to make a phone call to the Circus Café and to inform the hit squad the same second when Moran and his gang will enter the garage.


The morning on Thursday February 14, 1929, the temperatures were bellow zero and the streets were covered with snow and ice, thus causing a bad rush hour. The first North Side associate that came to the scene at about 8:30 a.m. was John May, then the two Gusenberg brothers, Frank and Pete, arrived at about 9:30 a.m. followed by James Clark, Adam Heyer and Dr. Reinhardt Schwimmer who was only a friend of some of the gang members. The last to enter the garage at 10:30 a.m. was probably Albert Weinshank, the man who very much resembled Bugs Moran and that’s when Byron Bolton from the lookout crew across the garage allegedly made a mistake. He thought that Weinshank was in fact Bugs Moran because from a distance he bore a big resemblance to Moran and so Bolton made the call to the boys at the Circus Café and informed them that their target has arrived. The killers were waiting in their cars in a rented garage at 1722 North Wood St. which was rented under a false name of “Frank Rogers”. With the signal from Bolton the killers headed for the SMC Cartage Company garage and took north along Wood Street for a mile to Webster Avenue, then east for two miles on Webster to Clark, which would have taken about fifteen minutes. The first car with the fake policemen arrived at 10:45 a.m. in front of the garage and the second car left the two killers in civilian clothes at the back of the establishment. The two “cops” entered the garage and their role was to persuade their victims to surrender their weapons without a fight, which was the reason behind the police uniforms. The “cops” rounded up the seven men up against the wall and then one of the “cops” opened the back door and let the other two men enter the garage. The two guys pulled out their two Thompson machine guns and the “cops” pulled out a shotgun and a revolver. Suddenly machine gun rifles were heard all around the neighbourhood and each Moran gang member was riddled with bullets. After the murder, the hit squad then staged their final part of the job and that was to confuse any witnesses as they reappeared on the street. The two hit men, who posed as policemen, took out the other two men as their prisoners, entered the fake police car and sped away. Also the lookout crew vanished at the same time and the killers returned to their previous location and left the fake police car at the rented garage on Wood St. and fled the area.


Eight days later, on February 22, the so-called “cleanup crew” which included Tony Capezio, Joseph Lolordo and Raymond Schulte, needed to get rid of the getaway cars. First they dynamited one of the cars in west suburban Maywood, the area where Claude Maddox and his family lived at the time and than they came back to the garage at 1723 North Wood St., to demolish the second getaway car, the phoney police black Cadillac. They mainly used acetylene torch, axes and hacksaws but Capezio allegedly made a mistake that nearly cost his life. While he was cutting through the gas tank with the acetylene torch, a fire broke out and blew him to the ceiling, while knocking him unconscious. The reason was that he forgot to empty the gas tank and so Capezio burned his arms and hands. His two companions took him to the North Avenue clinic, but when they arrived there they suddenly ran back out because they realized that someone might’ve heard the blast and might be calling the cops. This stunt allegedly earned Capezio’s nickname “Tough Tony.” Several years later bank robber Alvin Karpis, who was a close friend of Capezio's, also confirmed the story. So when the fire broke out in the garage the firemen who answered the call discovered the black Cadillac that had been partially demolished and called the cops. Some of the witnesses said that three men were seen leaving the burning garage after the car exploded and at least one was said to be injured.


The Chicago Association of Commerce immediately posted a reward of $50,000 for the arrest and conviction of the killers. And additionally the angry public collected another $10,000 for the reward. The city council and the state’s attorney’s office each added $20,000, bringing the total to $100,000, the biggest price ever put on the heads of gangsters. The main Capone connection within the investigation started when the cops found out that the man who rented the fake police car under the false name “Frank Rogers” also gave his address as 1859 W. North Avenue, which was a place just few doors behind the infamous Circus Café. That’s when the cops suspected that the Capone gang or the so-called Circus gang, which was a name invented by the newspaper men, had a hand in the bloody situation. They immediately arrested Claude Maddox who was found in his Circus Café and they searched the place and found a Thompson drum full of cartridges and also many overcoats strewn about the back of the joint and they even found a loaded .45 in one of the overcoats. Maddox was brought in the police station for questioning, but he was later released when he showed his alibi by being in court on an unrelated charge at the same time when the massacre occurred. Judge Peter H. Schwaba later confirmed Maddox presence in his court from 9:30 to 12:15 o’clock on the same day of the murders, which took at about 10:45 a.m. The investigation on Maddox didn’t really stopped since later they also found out that Maddox was once implicated in the collecting of a defence fund to pay the bail for three Capone gang associates Harry Burton, Frank Carlson and James O’Brien were arrested in a house near Crystal Lake for the kidnapping of some wealthy automobile dealer and the interesting thing was all three defendants were once suspects in a similar massacre that occurred in Ohio, when three hit men dressed as policemen entered a garage and killed five members of a beer gang. After collecting the so-called defence fund, Maddox obviously managed to sent the cash to the right places since during the trial of the three defendants, Burton was acquitted but the other two guys were sent to 5 years in jail. This action called for an investigation of the jury and one juror was sent to six months in jail for taking a bribe. Two weeks after the release of Burton the massacre of the Northsiders gang occurred, which throws the theory that Burton might’ve been one of the shooters.


The investigation continued with questioning all of the residents in the neighbourhood and the people who lived around the garage where the massacre occurred. When they questioned Mrs. Michelle Doody, she said that there were two guys in her rented apartment on the second floor, who constantly overlooked the street and rarely got out. The cops felt suspicious and decided to check out the apartment. During the search, they found a letter and a prescription bottle with the name of Byron Bolton. They didn’t thought about the significance of this clue until years later. But either way they started a search for Bolton for any possible explanation. But the thing was that by this time the out of town hit squad and Bolton fled the city and they were hiding out from any possible questionings by the police.


On February 26, 1929, Deputy Police Commissioner John Stege issued an order for the arrest of 17 well known criminals in the Chicago area. He believed that some of the men on the arrest list may have been the actual killers and the other might have knowledge about the situation. The first one to be arrested was Rocco Belcastro because his description given by a witness corresponded with the description of a man with a missing finger on his hand that drove the getaway car. Second on the list was Vincenzo Gibaldi a.k.a. Jack McGurn but he had a strong “Blond” alibi. His girlfriend backed his story and the cops found room service orders from the time when the massacre occurred. Again Claude Maddox found himself at the top of the suspect list and was taken for questioning. Maddox was a major hope for the investigation but he disappointed the cops because he kept his mouth shut and they had nothing on him since he again used his court alibi. The cops also arrested Joseph Lolordo because he lived next door to the garage where the demolished car has been found and another Capone member Danny Vallo, it was said, had voluntarily appeared at police headquarters when he previously heard about the arrests and warrants. Others arrested were Willie Heeney, Raymond Schulte, Tony Capezio, Rocco Fanelli, Tony Barone, Frank Diamond and also Bugs Moran and some of his friends and allies, including Sam and Joe Aiello, Rocco Griffo, William Rode, Charles Kakel, Frank Milici and George King. The cops also questioned the Jewish mob boss and Capone’s right hand man Jake Guzik. They had records that Guzik called Capone in Florida from The Congress Hotel shortly before, and after the massacre went down. In the end, no one dared to talk.


During another raid on a roadhouse in Forest Park, which was owned by the Capone gang, the cops also found a police star. The star no. 65 was issued to D. Alzell and it was very strange for the investigators because the killers in the massacre were dressed as policemen with police stars and the uniforms were never to be found. Also on March 5, 1929, the cops raided a liquor depot on the North Side which was operated under the auspices of Claude Maddox and Danny Vallo. During the raid, on the wall of the garage the cops noticed a paper with the names, home addresses, telephone numbers of two police officers and also information where they might be reached in ant hour of the day. But for unknown reasons Police Commissioner John Stege decided to ignore these two cases. My own believe is that these two obviously corrupted cops were the ones who provided the police uniforms and also information about one of the cars that was used in the hit. Since this was a big case and the public was outraged, maybe the Police Commissioner didn’t want any bad reputation for the Chicago police or even possible involvement in the massacre to be uncovered during this period. So he decided to push forward the idea that only paid killers from out of town were involved in the multiple murder case. So an angry group of wealthy Chicagoans decided to put up a large sum of cash for a scientific crime detection laboratory to be installed at Northwestern University. This lab, which was first of its kind, was completed by the end of 1929 and its first case was the St. Valentine’s Day Massacre. So they acquired guns and bullets from the police stations to determine whether the actual shooters were in fact real police officers. But the results came out negative and the forensic ballistics showed that in no instance was found a duplication of markings to indicate that any police weapons had been employed in the killings.


But the investigation really started changing that same time period or when Fred Burke killed a police officer and managed to elude the government for over a year. When the cops raided Burke’s house, they found a bullet-proof vest, two Tommy guns, pistols, and thousands of rounds of ammunition. Ballistics tests proved that both of Burke's Tommy guns had been used in the St. Valentine's Day massacre. The same tests showed that one of them had been used in the murder of gangster Frankie Yale. So now everyone who was allegedly involved in the Saint Valentine’s Day murders became too hot for the syndicate to deal with. The up and coming Chicago criminal administration decided to start a clean up, meaning to get rid of all of these hot heads that didn’t generate high sums of cash and were involved in unsanctioned robberies and hits that also might affect their illegal enterprises. But Burke managed to escape the wrath of the new up and coming gangsters because he was arrested back in 1931 at a farm near Green City, Missouri and was sentenced to life in prison. In October 1931, Fred Burke was visited by Capone’s old bodyguard and trigger man Phil D’Andrea at Marquette prison in Michigan. According to the prison’s Warden James Corgan, D’Andrea simply exchanged just few words with Burke and than left. Obviously D’Andrea’s visit was to make sure that Burke will keep his mouth shut about his previous involvements with the Capone mob or else. After that Burke was never pressed to answer any questions about the St. Valentine’s Day Massacre. In 1931 Nugent disappeared and legend goes that he had become a liability to the Outfit and had been taken out into the Everglades and fed to the alligators. Bob Carey heard about the news so in 1932 he decided to leave town together with his wife and headed to New York. According to police reports, on the night of July 29, 1932, Carey shot his wife to death, after which he turned the gun on himself. Some investigators believe that Carey and his wife were in fact killed by the mob. Fred Goetz also managed to remain as criminal force in Chicago. At first he controlled some of the rackets in Cicero for the Outfit under the auspices of Claude Maddox and Willie Heeney. After a while he wanted to claim independence which was his biggest mistake. Also one of his close associates Verne Miller was accused of helping gun down three policemen and a federal agent in an attempt to free bank robber Frank Nash during the infamous Kansas City Massacre. Story goes that Winkler gave information about the massacre to FBI’s Chicago field office. Goetz forgot about being constantly watched by the new organization and so on March 20, 1933 he was murdered in a drive-by shooting outside of a closed Cicero restaurant, the Minerva. Gangster Alvin Karpis believed that Frank Nitto ordered the murder and Maddox together with Heeney delivered it. Gus Winkler also remained as force for the Chicago Outfit by controlling the rackets on the North Side. And he also tried to gain independence from the Outfit. So on October 9, 1933 Winkler was headed to the beer distribution office of Charles Weber at 1414 North Roscoe Avenue. Upon his arrival Winkler was hit with 72 shotgun pellets by mob assassins. As he lay down in his own pool of blood, Winkler managed to gasp out the Lord’s Prayer before he died. William White's body was found in his Oak Park apartment, suffering gunshot wounds to the head and body, after a gunfight with two unidentified gunmen seen fleeing from the building on the night of January 3, 1934.


On January 8, 1935, FBI agents surrounded a Chicago apartment building at 3920 North Pine Grove, looking for few members of the infamous Barker-Karpis Gang, in connection with the kidnapping of banker Edward Bremer. After a brief shootout which resulted with the death of gangster Russell Gibson Bremer was rescued and the kidnapping gang was arrested. Among those taken into custody was also Byron Bolton. During the questioning, to the agents surprise, Bolton started talking. He pointed out the Barker gang’s main hideout in Florida and among other things he also claimed to have taken part in the infamous St. Valentines Day massacre. According to Bolton the main people involved in the massacre were Burke, Goetz, Winkler, and Nugent. But some of Bolton’s claims didn’t add up because he started throwing names like Maddox, Humphreys and Carey and these guys already had their own alibis. The problem was that most of these fellas were dead or in jail by now. Burke was sent to jail for the rest of his life and Humphreys was serving an 18 month term in Leavenworth prison for income tax evasion. The only suspect who was named in Bolton’s testimony and was still free on the streets of Chicago was again 35 year old Claude Maddox. On January 25, 1935, Maddox was arrested as he walked in his home at 2240 S. Oak Park Avenue, Berwyn and was brought to the police station for questioning again regarding the massacre. But a strange thing happened at the station. No one wanted to question Maddox regarding the slayings. It looked like every cop in the station was afraid of Maddox. The only cop who had the courage to ask him a few questions was Chief Detective John Sullivan. But Maddox didn’t say much except that he was in court during the time of the massacre or in other words he used his old alibi which was very useful. Bolton claimed that Maddox was indeed in court but he paid the corrupt judge to let him sneak for a while at 9 a.m. to accomplish the task with the other killers and than again returned to the court room before noon when his case was called. But Bolton’s testimony on Maddox was very unbelievable and if it was true it was very hard to prove it. Maddox’s court statement was supported by his attorney Tyrell Richardson and also by government officials. So Detective Sullivan had no other choice except to hold Maddox for the night and to release him the next day. The detective told the reporters “So far as I know, Maddox has no connection with the massacre and he’s not wanted here in Chicago for any crime”.


When the cops raided Bolton’s home they found numerous pictures of him together with Al Capone and other gangsters such as Fred Burke and Fred Goetz, which confirmed the Mob conference which occurred back in 1928. A veteran of the police force in Chicago Sergeant Samuel Loftus said that “Every detail that Bolton pointed out is true to my personal knowledge. I lived that case and as a matter of fact I’m still working on it. The Maddox angle is not only possible but I believe that is the answer to the puzzle of his alibi. We know that Maddox was involved but couldn’t prove it”. While leaving the police station Maddox allegedly said to his attorney “Well that’s one rap they can’t hang on me”. The shady director of the Federal Bureau of Investigation J. Edgar Hoover immediately dismissed Bolton’s testimony by saying “There’s not a word of truth in it” but the agent in charge of Chicago’s Division of Investigation D. M. Ladd said that “The Federal Agents haven’t even questioned Bolton regarding the massacre”. The only gangster that wasn’t mentioned in Bolton’s testimony, but was believed by every cop in Chicago that he had some involvement in the massacre, was Jack McGurn. The strange thing was that in 1936 the evening before Saint Valentine’s Day, or in other words the Massacre’s seventh anniversary, McGurn was killed by his peers while bowling and celebrating and that’s why I believe that McGurn’s demise on the same day when the massacre occurred 7 years ago wasn’t a coincidence, but it was a straight message from the boys. And that’s how it all ended.

Great info T, for some strange reason I'd never heard of Danny Stanton.
He sure had giant balls taking on the leadership like that..

Stanton previously rose in Chicago's underworld independently and later joined the Outfit somewhere around the early or mid 1930's and yeah, story goes that he was one tough, short-tempered and merciless motherfucker. He and Maddox took over the AFL Hotel and Restaurant Employees Union and the Bartenders International League of America. Maddox and Stanton controlled the Chicago Hotel and Restaurant Employees Local Joint Board and District Craft Council, in which all of the International's local unions held membership. The two gangsters plan was to destroy the local autonomy of all the member locals by setting up a master contract for negotiations with employers, thus the council would direct the destinies of over 35000 hotel and restaurant workers. Stanton mostly did the dirty work since he was a professional in intimidation and even killed few innocent people but the most interesting thing was that by 1940, Stanton belonged to the so-called “Big Four” in the union business, which also included Maddox, Murray Humphreys and Frank Nitto. This means that if he didn't got so much greedy, he might've rose in the organization on top level since he was a lucrative member and quite feared one. After the Stanton hit, the next year his brother-in-law and South Side gambler Robert Bock was also killed and Gus Alex was the prime suspect

COME ON TOODOPED TOP TEN !

great stuff as always toodoped.
thank you !

Great read, thanks for posting.

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