Whats up guys?! Im back with another story regarding the Outfit's history and its illegal operations. Two years ago i wrote down a small article regarding the Outfit's few greatest heists but later i though to myself, why not do the whole story regarding the activity. So all you readers out there, get your drinks ready, light up your splifs or cigs and enjoy the story 'cuz its a long one


“I don’t let thieves come around me, I don’t care what kind of scumbags they are. Once they are in the can, let the fucker stay in. They’re not like us guys. They’re just not like us guys. These fuckers that steal, they’re just not like us guys. You just can’t let them get close to you. You can let ‘em come with a bumper between you.” - Murray “Curly” Humphreys, high level and influential member of the Chicago Outfit


What is a theft? A theft is something which you take that doesn’t belong to you right?! So as I previously stated in one of my stories that the criminal activity such as theft is the main base of all criminal activities and also criminals from around the world. Sometimes people do it out of poor conditions and sometimes they do it because it is simply in their blood. For one to be a successful criminal, he or she should know how to steal. By “steal” I certainly do not mean just stealing apples from the fruit stand, even though many of the big time criminals usually start that way, but instead creating multi-million dollar schemes, which usually steals the food right out of the honest man’s mouth, or stealing something quite precious right under the nose of the police. You see, every possible thief is quite optimistic, meaning if they get caught 50 percent of the time, they think they got away with it. In other words, with thieves the glass is never half empty, but instead it’s always half full. For the thieves there’s always another day and another score. Sometimes these types of criminals spend their money so fast that they place the pressure upon themselves and so they have to go out and steal again and again.


Now, the activity such as theft or stealing can be divided in two main crime activities such as robbing and burglary. When somebody mentions “robbing”, the first few things which come on my mind are activities such as robbing banks in a violent style or robbing people right on the street or in other words doing “stick ups”. Also purse snatching can be a good example or robbing vehicles out of their stereos or tires. But the thing is that these examples of stealing can be quite noisy because some cars have alarm systems, or while robbing a bank, a shootout might occur with the police and the same goes for the stick ups. For example, some of the robbers might be “John Dillinger” type of guys, meaning people might get shot during the process by some random deranged and destructive persons or even violent juveniles. The potential for violence is present in every theft since it is very important for the criminal to stay undiscovered by the police and if discovered, he or she will not hesitate to use a weapon when apprehended. As for burglary, well this activity can be quite different rather than the previous ones.


The act of burglary has been around also for a very long time and it has always been called the “silent crime" mostly because the burglars often use stealth techniques to enter homes, business offices or safe rooms. Stealth crimes usually occur under the cover of darkness and in the absence of any witnesses or recording devices. Burglary is generally defined as the breaking and entering with intent to commit a felony or in other words, every person who enters any kind of structure, with four walls and a roof, with the intention to commit theft, is guilty of burglary. Being burglarized is like being raped, because you’re being violated and your home or business has been surreptitiously entered and your valuables have been stolen and in the end, you feel both rage and insecurity and believe me it is a quite frightening and nauseating experience because I personally have been through it. And the worst thing is that you just somehow know that the police won’t do anything special about it. But even with that sometimes I honestly admire the skills of these individuals because it is not very easy to get in a protected building and then get out unnoticed with tons of cash.


According to some theories there are three types of burglars on this world, such as the professional burglars, the ordinary thieves and the opportunists. An “opportunist” is often a drug addict or a misled teenager, who goes out looking for a business or home that he thinks he can break into easily and get away quickly. There’s almost no kind of planning prior to this fast crime and that is why the perpetrators usually are easily caught by the police. But these individuals can be also quite dangerous. Narcotic addicts that are taking on daily basis stuff like heroin, cocaine especially crack cocaine, speed or meth, will usually resort to burglary with the possibility of assault just to obtain the necessary cash so they can sustain their dirty habit.


The so-called ordinary “cat burglars” are usually half specialized thieves, who often commit crimes like small burglary and any other type of small crime. They use simple tools such as picklock, crow or key bit and they usually target business offices, drug stores and homes that have less protection than high-end establishments. Something like small retail stores and homes known to contain valuable stuff such as cash, jewellery, clothes and electronic equipment. The chances of catching these criminals are 50/50 because with a little bit of luck, they can easily get away with your stuff.


As for the professional burglars, they usually target big mansions, major businesses, banks and other high-end targets. Prior to becoming an expert in the job there is much experience, which can only be absorbed by first going through the previous stages. After gathering all the experience, the burglar becomes more sophisticated like for example, prior to committing the burglary, the professional burglar performs surveillance on the target. Although most of the targets have the best alarm systems in place, the professionals use their knowledge and specialized tools to disable these systems. They also have the skills to open any vault, safe or other secure objects or places with the help of tools such as acetylene torch or electric arc, burning bar, thermal lance, oxygen lance, or any other similar device capable of burning through steel, concrete, or any other substance, or by use of nitro-glycerine, dynamite or gunpowder or any other explosive.


Since they can be very lucrative, sometimes these professional burglars are “backed” by other high profile criminals such as corrupt officials or mobsters. For example in Chicago, the city where crime always thrives, for many decades existed a close fraternity between professional burglars and racketeers who used the city as a central location to pull jobs all over the country. One of the most powerful organized crime groups, known as the Chicago Outfit, ruled the underground for almost a century and most of its members started their professional criminal careers as burglars. Members from high profile organized crime groups such as this one, usually have contacts to people such as security guards or ordinary staff workers, who for a certain price deliver info’s to the gangsters regarding certain targets. In most cases these corrupt “inside” individuals don’t have connections to professional burglars, and so instead they lurk around the neighbourhood and start asking questions and before you know, they get connected to higher level criminal, who already had connections to various burglars.


Back in time, during the 1920’s and 30’s in Chicago, the “silent crime” such as burglary was on a very low and almost unprofessional level, since it was the time period of the lucrative bootlegging racket and so the act of burglary was mostly done by youthful criminals. For example, one of the Outfit’s widely known crime bosses Sam Giancana started his long and infamous criminal career as a quite unprofessional burglar on the city’s streets. At this point, Giancana hung around with the infamous 42 gang and terrorized the streets in the company of other young criminals such as Dominick Caruso, Tony Orlando, Tommy Russo and Joey Sypher. One day, on the morning of July 3, 1926, Giancana, Caruso and Sypher burglarized a dress shop at 2663 North Clark Street and managed to steal 50 dresses valued at $35 each. When they drove off with their car, a police patrol followed them right behind and then the expected occurred which was the everyday car chase. Suddenly the young criminals crashed their car in a nearby sidewalk, Giancana managed to run away but Caruso and Sypher were apprehended by the police. Few hours later Giancana was also arrested and at the police station, he and Caruso kept their mouths shut while Sypher decided to plead guilty and admitted that he was the one who planned the burglary, thus saving his two companions. Two years later, on November 17, 1928, Giancana, Orlando and Russo started using the infamous “hole in the wall” burglary method, by burglarizing a store at 3947 West Madison Street, with the help of cutting the bricks out of the wall of the building. Obviously someone reported all the noise and the burglars were apprehended right there on the scene. The cops found the hole in the wall and the three burglars near by with all kinds of burglary tools in their hands and one revolver on the ground close to where Giancana was standing. Four hundred feet from the scene, the cops also found the “getaway” car which later was traced directly to Giancana, who in turn was covered in mortar dust. On March 12, 1929, all three defendants were sentenced from 1 to 5 years in the penitentiary.


As you can see, because of the high unprofessionalism in the way of burglarizing, by now the style of robbing was on first place by doing stick ups and “cleaning out” stores, restaurants and parties with high clientele, jewellery stores, banks and social clubs. For example, a bank robbery in those days was the same as horrifying as the ones in the movies, with a band of pro-criminals, just loving their job, with bullets flying all around and hostages jumping from cars during high speed chases. For example, one of the Outfit’s most infamous non-Italian crime bosses Lenny Patrick, during his youthful days, participated in one chaotic bank robbery. In 1933, 20-year old Patrick together with his brother and few other robbers, “cleaned out” the State Exchange Bank of Culver, Indiana. When the fearsome gang entered the small town, all of the citizens stood up on their feet and in just few moments, all hell broke loose. While few of the robbers entered the bank, one member remained outside and exchanged bullets with a group of local vigilantes. When the rest of the gang heard the shots, they immediately took one hostage each, got out, entered their car, and while shooting at everyone, they quickly fled the scene. This wasn’t the end of it, but instead two cars filled with vigilantes went after the robbers. During the chase, the robbers ordered for their hostages to jump from the car, and they all proceeded into the combined woods and swamp which was located near the little town. In the end, all of the robbers, including Patrick, were caught, convicted and sentenced to 10 years in prison. In fact, all of this chaos occurred for lousy $12,000.


The problem was that during those days the banks did not held more than $15,000, which was a quite small amount for such a risky operation. I mean don’t get me wrong, even ten grand was considered a lot of money in those day, enough to buy a good house, but it wasn’t something to risk your neck for. Later, some of the so-called stick-up men got “lucky” and ended up in jail instead of being shot dead by the cops and prison is always considered as “college“ for the up and coming criminals, or at least that’s how things went back then. During their stay in jail, the smarter ones decided to get mixed with more sophisticated criminals, like members of the infamous Chicago Outfit, who in turn took these guys under their wings by providing them with financial support in finding “jobs” and such. Now, some of the robbers remained independent, which was a rare occasion, some elevated to other criminal activities, thus leaving the stick-up business behind but some remained in similar activities or switched to burglaries.


For example, during World War II many of the criminals were presented with many new opportunities such stealing ration stamps. Upon the American entry into the conflict, the government released coupons for sugar, gas, and many other items which were in a short supply at the time and many Americans were forced to conserve on everything which meant sacrifices for all. Since the federal government needed to control the supply and demand, in the spring of 1942, the Food Rationing Program was set into motion and later coupons for coffee were introduced in November, and by March of 1943, meat, cheese, fats, canned fish, canned milk and other processed foods were added to the list of rationed provisions. In no time, this deeply affected the American way of life for most, including the gangsters but in a different way. Now many of the high profile mobsters devised highly lucrative schemes by stealing the stamps and later re-selling them on the black market and with the help of this so-called stealing scheme, many of the most infamous mobsters jumpstarted their criminal careers and made a fortune, from Carlo Gambino in New York to Sam Giancana in Chicago.


One of Giancana’s guys in the ration stamp stealing business was William Daddano, a young criminal who also managed to introduce himself to the Chicago Outfit by burglarizing federal safes and stealing millions of stamps in the process. This criminal activity was mostly practised by the West Side faction of the syndicate, particularly the younger generation. At the time, many young hoodlums from that area, names such as Giancana, Battaglia or Fratto were already brought into the criminal brotherhood in the city of Chicago, and so other and also younger hoodlums reached for the same “success” such as Daddano, or guys like Sam DeStefano and Marshall Caifano. In those days if you stole a huge amount of sugar ration stamps, for example, and somehow you managed to get four or five tons of sugar, the price of that amount on the black market was approximately $500,000 or almost 7 million dollars in today’s money. According to some reports, Daddano stole 4 million ration stamps which worth over $100,000 on the black market but too bad for him since shortly afterwards he was caught and was sent to jail. Even though he went to prison for only a year, Daddano stood proud in his jail cell because he never said a word to the investigators and took his punishment like a real gangster. Because of that, Daddano quickly became recognized as a stand-up guy among some of the top level guys of the Outfit. It was because of guys like Daddano, the government was forced to double its security and control over the ration stamps and so many of Daddano’s associates such DeStefano changed their tactic by making fake ration stamps. By the end of the war, restrictions on processed foods and other goods like gasoline and fuel oil were lifted, but the rationing of sugar remained in effect until 1947 and so that same year, DeStefano also joined his buddy in prison after the cops caught him for creating and trying to pass off fake sugar ration coupons.



William Daddano


While some burglars went to jail for stealing or making fake ration stamps, times slowly has changed and so many of the free burglars returned to the old ways by stealing cash, gold or precious jewels. During the early 1950’s, in Chicago, the most prominent burglar and fencer at the same time, was Carl Fiorito, a notorious criminal with long police record of more than 40 arrests. I believe that this guy was the real so-called “King of Thieves” because he knew and worked with almost every possible thief around the country and he was also the prime so-called “job receiver” since he knew every possible Outfit member in his own city. He was the city’s first and real professional burglar, same as the ones that you see in the movies, who in those days gave the word “burglary” a special meaning.


Fiorito started his infamous criminal career during the early 1940’s, with two Outfit-connected individuals and former burglars from the Northwest area, known as Paul Labriola and Jimmy Weinberg. Besides extortion, these fellas were deeply involved in the robbery and burglary businesses and later in reselling all of the stolen property but above all, they sold stolen truck parts, an operation in which Fiorito found his true qualities. By 1950, Fiorito made another quite profitable connection, which went by the name of Dave Yaras, a known Outfit killer and extortionist from the West Side or to be precise, from the Lawndale area. During this period, Yaras left his crew to his long time partner Lenny Patrick and started spending more and more time in Florida where he expended the Outfit’s rackets. And since Florida was considered by the American Mob as an “open territory”, everybody operated freely as long as they all stayed in their spots.


For example in January, 1952, at St. Petersburg in Florida, Yaras, Fiorito and one James McCarthy managed to steal four cases filled with expensive jewellery which were valued at $40,000. In March that same year, Yaras and McCarthy were arrested during the investigation but were later released since the cops had no hard evidence to put them in prison. In fact, McCarthy was one of the biggest jewel fences in the city of Chicago, and so with the help of Yaras, he managed to get stash from thieves all the way from Florida. Sometimes they received more than a million of dollars in jewellery from wealthy couples at the Florida resorts, usually during the winter months. According to some FBI reports, during this period much of the stolen loot around the Miami area was later disposed in Chicago and so according to this, I personally believe that Yaras was the prime connection for Fiorito in making new criminal relationships with professional thieves from around the country.



Carl Fiorito


But the thing was that Fiorito’s prime territory was way back home in Chicago where all the chaos was thriving within the underworld. So after the slayings of his two close friends and partners in crime Labriola and Weinberg in 1954, Fiorito still operated in Chicago but this time, his new “sponsor” became obviously the West Side faction of the Outfit since they were on the up and up within the organization or to be precise, his bosses became Fiore Buccieri and Sam Giancana, one was the “capo” of the infamous Taylor Street crew and the other was the current under boss of the whole organization. Buccieri was one of the most sadistic and greedy individuals which the Outfit has ever witnessed and Giancana was no different, and even though Fiorito wasn’t considered by law enforcement as official member of the Chicago Outfit, still he had direct contact with these two individuals. As I previously said, he was also connected to many high profile burglars and criminals from Chicago and also from around the country such as Joe Merola from Pittsburgh, or some other infamous “faces” such as the Priorello brothers, George Grisby, Theodore DeRose, George Peara, and Wilson Williams.


Also one of Fiorito’s partners such as William Dentamaro, often travelled to Florida where he spent most of his time and together they managed to orchestrate many “fine jobs”. Dentamaro also worked with some of the New York crime families but he was also closely associated with Santo Trafficante Jr., the top crime boss from Tampa and according to some reports, Dentamaro was considered a member of that same family. Since Florida became the place of business, by 1957, Fiorito received “jobs” directly from Dave Yaras, who by now also spent most of his time down there. There are numerous government reports on meetings between Fiorito, Yaras and Dentamaro in various locations between Chicago and Miami and they became prime suspects in numerous burglaries and heists. For example, in February, 1957, the trio made a theft of $60,000 worth of jewellery in Miami and later the stolen loot was quickly transferred to Chicago by one Peter Arnstein, where it had been exhibited to Ken Gordon, who was a known Chicago fencer for stolen jewellery. Later the usual practice was for Gordon to call the victim and to offer him the loot back for a certain price and in case if the victim refused, then Gordon had a very easy way of quickly disposing the stolen stash.


Now, the whole so-called “procedure” of disposing the stolen loot, went something like this: after the arrival of the stolen merchandise in Chicago, the first guys for contact were Giancana’s people on the street such as James Torello, Steve Tomaras, or Donald O’Brien, who constantly received information about the arrivals of expensive stolen loot. After that, one of these guys usually contacted one of Giancana’s personal bodyguards known as John Mattassa, who in turn would arrange a meeting at a bar which was known as the Stop Light Lounge at the corner of Cicero Avenue and Roosevelt Road. Besides secretly owning the whole place, Giancana also had a big safe in one of the back rooms, which was actually a safe within a safe. Inside Giancana kept all of the stolen loot and the only two individuals who had the combination to the safe were him and Mattassa. Many buyers or “fences” were brought out to that location almost on daily basis and were shown the stolen merchandise by the thieves, such as Fiorito, usually in Mattassa’s presence. Also from time to time if some of thieves brought something nice or quite expensive, Giancana would’ve just taken it for himself and never bothered to pay for the damn thing. Story goes that sometimes Giancana’s safe was so full of stolen merchandise, and so his people needed to take some of the stuff to their own houses for the night and then return it the other day.