But not everyone from the old gang was welcomed in the Outfit. By 1933, Jack McGurn was demoted from the organization and was placed on the shelf. The reason was that he was a heavy drinker, narcotics user and above all a degenerate gambler. He lost all of his money and was constantly harassed by the investigators as the main suspect in the St. Valentine’s Day massacre. He only had the skills for killing a man but by now the Outfit had an army of killers and didn’t need McGurn’s services anymore. He didn’t generate any real money or controlled any of the rackets so in plain English, he was useless. One day newspaper reporters found McGurn in some restaurant and asked him if he had any connections with the kidnapping of Jake the Barbers son, Jerome Factor. McGurn replied “Boys I ain’t made a payment on my house, the roof over my head, in 11 months, so I guess I’m gonna lose the place to foreclosure. So if I snatched Jake’s kid, believe me, I would have collected the dough long before this”. But some guys of the old Circus gang like Willie Heeney still had respect for old boy McGurn. By now Heeney was involved in the labor extortion business, bookmaking operations, white slavery and narcotics trafficking, so he was way up in the ranks over McGurn. So Heeney decided to take McGurn under his wing and give him another chance. Heeney knew that McGurn didn’t have the brains for the big businesses so he gave him the job for running numbers and also selling dope in the Black neighborhoods. Both of them were dope addicts so we can only imagine how the business for McGurn was really going. But two years later McGurn made a master plan about importing heroin from the Caribbean to Chicago and to flood the rest of the country. But the problem was that he didn’t know the Outfit’s boss Paul Ricca already made a deal with New York’s Charles “Lucky” Luciano and Meyer Lansky to establish dope routes from Cuba to Florida and the rest of the country. McGurn also asked for financial backup for his international drug smuggling ring. The bosses refused and also dismissed him again from the organization.
Jack McGurn
Things got more complicated when 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 a 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 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 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”.
Claude Maddox has his picture taken by police photographer William Mathews in Chicago
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. A veteran of the police force in Chicago, Sergt. 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 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”.
Byron "Monty" Bolton
Bolton (middle) with two agents
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. I believe that he was one of the main logisticians for the slayings but there was no proof for him being directly connected with the massacre. But the new criminal organization which was headed by Nitti and Ricca didn’t want to risk any chances since McGurn was out of favour and was also displeased by their leadership. He was all done in the rackets as far as Ricca was concerned. McGurn didn’t respected Ricca’s order and continued his drug peddling operations in Chicago. Ricca was one of the few rare bosses of the Outfit who would gave you second chance to retire and if you ignored his offer,that was one way ticket to the graveyard. So that was the case with Jack McGurn. So in 1936 the evening before Saint Valentine’s Day, or in other words the Massacre’s seventh anniversary, McGurn went bowling at the second floor of the Avenue Recreation Rooms on 805 North Milwaukee Avenue which was owned by Ricca’s henchman Willie “Smokes” Aloisio. McGurn was called by two of his former gangster friends, Frank “Three Fingered” White and Claude Maddox, to join them for few games. The three men entered the bowling alley and according to witnesses 15 minutes later three men with bandanas on their faces walked in and yelled “Stick ’em up!” One of the three men fired a warning shot in ceiling and everyone in the establishment has hit the floor. So one of McGurns bowling buddies approached him and whispered “This is for you, you son of a bitch!” and than shot McGurn behind his right ear. It was a set up. McGurn fell to the ground and the assassin fired few more shots. The three stick up men fled the scene while White and Maddox, that came with and killed McGurn ,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’ and White’s involvement in the hit. 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 message from Ricca and the boys.
Jack McGurn dead
Right now I want to ask the most important question regarding the slayings of everyone who allegedly were involved in the massacre. Why Claude Maddox or Willie Heeney remained alive and continued to rule the streets of Chicago? The answer is simple, and that is because they were generating a lot of cash for the new organization and were very loyal to their superiors. By the mid 1930’s the Chicago Outfit was taking over every union in the city. Like for example the president of Chicago Moving Picture Operators union Thomas Malloy was slain by Outfit assassins on February 4, 1935. Half of Malloy’s head was blown to bits by a shotgun blast. Suspects in the murder and immediately arrested were Claude Maddox, Ralph Pierce, Sam Hunt and Leslie Kruse. Later all of them were released because the cops had no evidence to hold them up. With Malloy out of the picture the Outfit took over the projections union and looked forward for the Movie Industry and in 1936 they succeeded in their goal. By the late 1930’s Claude Maddox together with Danny Stanton, feared ex-Capone enforcer and extortionist, 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. By 1940 Maddox alone was in control of local 450 of the Bartenders, Waiters, Waitresses, and Miscellaneous Workers' union at 2137 South Cicero Avenue, Cicero. Maddox was listed in the local’s books as a member and officer and in 1941 he was a delegate at the International's convention in Cincinnati, Ohio as a representative of local 450. When the news reporters learned about Maddox’ involvement they asked William Kerr, the secretary-treasurer of the Cicero local, if this is true? Kerr denied any connection between Maddox and his union but the records and investigations said otherwise. The same year the Chicago Crime Commission listed Claude Maddox as a Public Enemy number 8 and also reported him as being one of the biggest threats for the unions in the city. Maddox was also assisted in the matter of establishing control over local 450 by Louis Romano, who was head of Local 278 of the Bartenders Union in Chicago. By now Maddox belonged to the “Big Four” in the union business among other gangsters such as Murray Humphreys, Danny Stanton and Frank Nitti.
Claude Maddox
Danny Stanton was a real hot head and started to muscle in on every possible union in the City of Chicago and even on those unions that were already in control of the Outfit. With his imposing figure, Stanton was a professional for intimidation. Previously he rose as a criminal independently and later was absorbed by the former Capone gang. But during the early 40’s and with the massive taking over of the unions, Stanton blinded by his ruthlessness, started making problems for the Outfit in general. He started quarrelling with Claude Maddox over the Restaurant and Bartenders union scheme because he wanted a bigger share. 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. At the same time the whole top echelon of the Outfit, including Nitti, Ricca, Campagna and D’Andrea, was indicted for extorting over a million dollars from several Hollywood studios. Rather go to jail, Nitti decided to shoot himself in the head with a loaded .32 caliber revolver. So maybe Stanton figured with Nitti dead and with some of the big shots were going away for awhile, his chance was now or never. Stanton enjoyed many years of wealth from his connections to the Outfit but now those times were over. On May 5th 1943, just before midnight, Stanton and one of his closest associate Louis Dorman were having drinks in a bar at 6500 May Street. Suddenly Outfit hitmen William Block and another hitman kicked the back door of the bar and blasted three shots with their shotguns. Dorman got one in the back and Stanton got one in the back of the 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. That was the end of Danny Stanton. A young beautiful blonde by the name of Cecelia Ashley was one of the witnesses who was sitting next to the dead gangsters and saw the killers. The other day she learned that the police knew about a “blonde” woman sitting near the victims. Her friends advised her about going to the police so she decided to go for it. On May 8, Miss Ashley started 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. Patrick Collins, of the police department, and Assistant States Attorney Francis McCurrie stated publicly that Stanton had refused to take any orders from or surrender any of his powers to Claude Maddox. There’s also another report that Maddox was then attempting to take over the checkroom attendants' union which up to that time had belonged to Stanton. Anyways Stanton became just another example that no single person was above the organization.
During the mid 1940’s, even with most of his friends from the top echelon were sent to jail, Claude Maddox’ business was booming. One of his underlings from the old Circus gang days Tony Accardo became the front boss of the Chicago Outfit. Accardo had a great respect for his older companion and placed him in charge of the few biggest union rackets in Chicago. Accardo also granted him few more gambling spots on the North Side and also gave him few race tracks operations.
Tony Accardo
Now Maddox as a senior member of the organization was riding high and also had his own voice in Chicago’s criminal commission. He remained as the prime force in Cicero together with his older associate Willie Heeney and other gangsters such as Joseph “Fifke” Corngold, Ralph “Bottles” Capone and another ex-Capone gangster Tony “Mops” Volpe and they were all overseen by jailed boss Louis Campagna. One of their hang outs was a gambling spot known as El Patio Tavern at 5914 Cermak Road, Cicero. These old timers made money and managed to survive the pre-Capone era, the Capone era, the forming of the Chicago Outfit and World War II. Guys like Maddox didn’t serve more than a year in jail and also had a constant flow of cash through the decades. By now two of Maddox’ prime underlings were Robert Ansani and Joseph “Joey O’Brien” Aiuppa. Together they were operating the Towne Hotel in Cicero, which was also a big gambling spot filled with prostitutes. Maddox knew Aiuppa since the 1930’s through his connections with other various gangs. Aiuppa used to work closely with the infamous John Dillinger gang and also Barker-Karpis gang. He used to provide these gangs with weapons and hide outs. In 1935 seven gangsters including Aiuppa, were arrested regarding various hold-ups on golf clubs in Chicago. Aiuppa was aksed who he was working for, he answered “You know me, I’m working for Johnny Moore”. Within few minutes Aiuppa and the rest of the gangsters were released. By this time Aiuppa mostly ran the gambling and bookmaking operations for Maddox and was the owner of the Greyhound Recreation Center at 4031 West Cermak Road. Maddox and Aiuppa also owned another famous club in that area known as the Turf Nighclub. It was a place with many gambling operations and also filled with prostitutes. Another gangster who worked at the club and launched his criminal career from that place was Gus Alex. The Cicero crew also owned few more joints such as the Paddock Lounge, the Post Time Lounge and the Circle Club. Aiuppa became a charter member of Maddox’ Local 450 and during the mid 1930’s he was arrested during his connection to Maddox regarding an aggravated assault. Later the case was dismissed and Aiuppa was released. By the late 1940’s Claude Maddox, Joey Auippa and Robert Ansoni were partners in the Taylor & Company organization which was a front for transportation of gambling devices, like slot machines, around the city of Chicago and beyond. They made over half a million dollars a year from this enterprise. Maddox and the rest of the gang owned another firm which was called the AMA Advertising Company. From here they manufactured silk screen process. Aiuppa and Maddox also managed to spread their bookmaking operations in Melrose Park with the help of their old associate and also boss of that area Rocco DeGrazia. In other words Aiuppa was Maddox’ number one guy. According to underworld resources Aiuppa once bragged that he was the number two guy (after Maddox) in Cicero.
Joey Aiuppa
The infamous Cicero crew also played a major role in securing the parole for their jailed superiors in the Hollywood studios case. If the bosses remained in jail for a long time, that would’ve been a big downfall for the mob in Chicago and maybe a reason for an internal war. The first step was to pay off the tax debts that Ricca and Campagna owed to the U.S. because a prisoner cannot be paroled if he has another case pending.There were back taxes on the part of Campagna and Ricca to the extent of about $500,000. Claude Maddox, Willie Heeney, Fifke Corngold, Ralph Capone and Joey Aiuppa together collected over $100,000 donation for the bosses. Through their connections they managed to settle the $500,000 debt for about 20 cents on the dollar which at the end was around $100,000. Heeney carried the cash to St. Louis and turned it over to some prominent political figures, who played a leading role in getting the bosses released. Than the Cicero guys collected another $160,000 from the other top guys in the Chicago Outfit and gave it to the bosses’ lawyers. One of the lawyers went to the judge that led the parole hearing and placed the money on his desk and said "This is for Paulie", meaning Paul Ricca. The final step was to influence the parole board and rumours are that the Parole Board members accepted a $500,000 bribe. So on August 13th, 1947 the bosses were set free after serving just 3 years and 4 months of a ten year sentence. In 1948 Heeney was called and questioned before a federal grand jury in Washington about the alleged conspiracy for the release of the Chicago bosses. Heeney explained that he never contributed a penny toward getting the paroles. So now the Cicero chiefs Claude Maddox and Willie Heeney gained a big respect in the eyes of their superiors and the Outfit in general. They received a reputation as a true stand up guys.
The same year Chicago’s first big crime boss Al Capone had a stroke. Capone managed to regain consciousness and started to improve but contracted pneumonia and later on January 25 he suffered a fatal heart attack and died. Capone was buried аt Mount Carmel Cemetery in Hillside, Illinois. Most of the top echelon of Chicago’s underworld didn’t show up at his funeral because of the publicity but according to investigators Willie Heeney and Claude Maddox were there. Again these guys showed their huge loyalty even to their long gone former superiors like Capone. They didn’t care about the public attention or the press. They understood the fact that the world already knew about their shady past and presence so why hide?! Years later Virgil Peterson, the head of Chicago Crime Commission reported that Maddox, Joey Aiuppa and Robert Ansoni were pallbearers at Capone’s funeral which was a closed affair.
By 1950, Claude Maddox had control over most of the unions in Chicago such as the Produce Drivers' Union and Local 703 at 216 South Ashland Avenue, the Picture Frame Workers Union and Local 731 at Southwestern Avenue, the International Hodcarriers Union at 814 West Harrison Street, the Movie Operators Projectionists Union Local 110 and of course his favourite the Hotel, Club, Restaurant Employees, and Bartenders International Union, Suburban Local 450 at 2137 South Cicero Avenue. Maddox’ frontman and international vice president of Local 450 was James Blakeley. Blakeley was also a member of the huge Hotel-Motel Service Workers, Drugstore, Sports Events and Industrial Catering Union, Local 593 at 10 North Wells. By this time Maddox’ placed the Lardino brothers, John and Dan, as overseers of his union enterprises. The brothers were both known as killers, extortionists and members of the Chicago Outfit. Blakely constantly reported to John Lardino and also gave the money from the scheme directly to him. Lardino was also a member and consultant for Local 593 and received additional $100 a week for his services. Later Lardino held a $30,000-a-year job as administrative director of the local. Investigator reports say that with the help of the Lardino bros, Claude Maddox allegedly was receiving $10,000 a month from all of these unions.
On July 13 (Friday the 13th), 1951 Maddox lost one of his oldest and closest associates Willie Heeney. 63 year old Heeney died of tuberculosis in the Mercy Hospital in Cicero and was buried in Mount Carmel Cemetery. Many high profile Outfit members came to his wake including his old buddy Claude Maddox. He was remembered in the underworld as a killer, gambling boss and as a cornerstone of organized crime in Chicago.
By 1952, 51 year old Maddox became one of the elderly kings of Chicago’s underworld. In August Maddox was the host of a lavish gangster champagne party right under the noses of the police in Chicago. The occasion was the wedding of his eldest son Bob Maddox. The party was a gala affair with a12-piece orchestra and the vintage wine flowed freely. The newsmen who motored to the country club were urged not to enter the clubhouse by 10 husky bodyguards in tuxedos. The wedding was visited by more than 1000 guests including Paul Ricca, Tony Accardo and the new up and coming star in the Outfit Sam “Mooney” Giancana.
Maddox also loved horses and during this period he devoted a portion of his energies to horse racing. He owned a lot of stables and race track stock around Chicago and other areas and also owned thoroughbred horses and ran them under the names of "stooges". In 1953 "Mr. Moore" became a celebrity in the fashionable show horse set by winning ribbons with horses kept at the Onwentsia stables, near Lake Forest. His main establishment was the Pat Kay horse stable in an exclusive country area north of Barring, Cuba Township, Lake county in which numerous high profile society figures resided. The ownership was listed as Mr. John Moore and Mrs. Alice Moore, his wife. His son Bob and William Campbell were the frontmen for these stables. Maddox knew a lot of veterinarians, trainers, jockeys and bookies, and story goes that he fixed a lot of racings and made a fortune. Two of his business partners and also stable owners in this lucrative enterprise were Sam Hunt and Louis Campagna. In October, 1954 the officials in Cuba Township thought that office of the Pat Kay stables would be a good central location for a polling place for the 512 voters. But the ownership of the stables by Maddox was highly publicized in a recent investigation of gangsters in horse racing. So the township and county officials decided to move the polling place to the Biltmore Country club. Joseph P. Welch, the Cuba Township supervisor said "I was just as surprised as anyone else to learn that Mr. Moore was in fact Claude Maddox." Maddox also used to sell some of his horses to many famous and rich people. In one deal he sold three horses for $35,000. During this period the government officials unleashed a big investigation on the horse race business which resulted with the convictions of many Outfit associates and hirelings.
