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Giacomo "Big Jim" Colosimo

"Diamond Jim" or "Big Jim" Colosimo was the founder of the infamous Chicago Outfit, Illinois' most successful criminal organization. He also has the dubious honour of co-founding the Midwest's White Slave Ring.

Big Jim Colosimo Giacomo Colosimo was 10 years old when his family left the Southern Italian province of Calabria and emigrated to the US. Giacomo, or Jim as he became known, grew up in Chicago's First Ward, shining shoes and selling newspapers to scrape a living. As a teenager, he began supplementing this income with pick pocketing, a crime at which he excelled. He was 18 years old when he began engaging prostitutes to work for him. Early in his career, he took up the Italian practice of sending Black Hand letters to wealthy citizens of Chicago. These anonymous messages threatened violence unless money was paid, and were usually signed with an imprinted black hand.

While working as a pimp, he also had a legitimate job with Chicago's street-sweepers. He soon rose to the rank of foreman, which is not surprising since the street-sweepers were almost exclusively Italian and he was one of the rare few who could speak English. He also organized a social and athletic club for his workmates, and naturally much of the profits found their way into his pocket. With his job, the club and his women, he earned enough money to open a pool hall in the First Ward. Through his prostitution racket, he gained a reputation as a tough criminal, and attracted the attention of the Democrat Party.

The aldermen for the First Ward at the time were two Democrats, saloonkeeper Michael "Hinky Dink" Kenna and a bathhouse owner named "Bathhouse" John Coughlin. As aldermen, Kenna and Coughlin had a lot of political clout in Chicago and consequently, they were able to control the city's brothels. They hired "Big Jim" to collect protection money from the city's pimps. Those who paid felt secure in the fact that their businesses would remain untouched by the police.

One madame who bought this protection was Victoria Moresco, a woman who fell in love with Big Jim. The two were married in 1902. By then, Colosimo owned a pool hall, a saloon , and now his wife's bordello, and combined with his share of the generous contributions to the Democrats, he was fast becoming a wealthy man. He and Victoria opened many more prostitution dens and muscled in on the businesses of other pimps. At the height of his power, Big Jim owned or shared in the profits of an estimated 200 whorehouses.

Prostitution was a booming industry in the Levee district, and supply was far outweighed by demand. Chicago needed a new source of hookers, so the Colosimos set up Chicago's White Slave Ring with another married couple, Maurice and Julia Van Beaver. The slavers kidnapped young girls, beat and raped them into submission and sold them to pimps for $400 each. They specifically targeted immigrant girls who could not speak English, making it more difficult for the girls to get help. Many of their victims were underage teenagers who were easier to control and more popular with the customers. Most of these girls were sold to slavers in other states so that it would be more difficult for their families to track them down. The Colosimo's and Van Beavers also supplied local pimps with girls kidnapped from out-of-state cities. The White Slave Ring had contacts in Kansas City, St. Louis, Milwaukee and New York.

Colosimo's wealth did not go unnoticed, and in 1909 he became the target of a Black Hand letter, similar to the ones he used to send. Fearing violence from these hidden blackmailers, he agreed to the terms of the letter and paid up. However, it wasn't long before the next letter arrived, and he realized that no matter how much he paid, they would continue to harass him. The only solution was to ambush his tormentors. The drop-off point for the money was at Archer Avenue and Colosimo left an empty suitcase in place of the money. When the three extortionists arrived to collect it, they were shot dead by a group of gangsters lead by Johnny Torrio, Victoria Colosimo's nephew brought in from Brooklyn, New York.

"Big Jim" was impressed with his wife's nephew and Torrio became his contact in New York. Over the next few years, Johnny came to Chicago several times to do business with Colosimo. Eventually Torrio moved to Chicago to work for Colosimo permanently. By this time, "Big Jim" had become something of a celebrity, mixing with judges, politicians and the stars of the entertainment industry. His gang, known as the "Outfit" was the most successful criminal organization in Illinois, and he had become known as "Diamond Jim" because he displayed his wealth by covering himself in jewellery. His restaurant, Colosimo's Café had become a Chicago institution; the eating place of the rich and famous. Opened in 1910, the Café was located on 2126 South Wabash Avenue.

As "Diamond Jim" enjoyed his wealth and popularity, he came to rely more and more on Torrio to run things for him. Torrio revamped the Outfit's brothels, decorating them lavishly and populating them with polite, well-dressed hookers. Wealthier clients who had previously been put off by the sleaziness of these houses began to arrive in larger numbers. Torrio also became the manager of several of Colosimo's saloons and restaurants, including Colosimo's Café. Then Big Jim got another Black Hand letter, this time from a gangster named Giacomo "Sonny Jim" Cosmano. As he was collecting what he thought was $10,000 cash, Cosmano was attacked by Torrio and hit in the stomach by a shotgun shell. He survived, but fled from Chicago and as a reward, Torrio became the Outfit's chief lieutenant.

In 1911, Torrio bailed Colosimo out of trouble once more. A victim of the White Slave Ring escaped her captors and was being hidden by the police while they prepared indictments against Colosimo, Torrio and Maurice Van Beaver. Through his old gangmates in New York, Torrio discovered that the escaped witness was in Bridgeport, Connecticut. Soon afterwards, two men identifying themselves as federal agents approached the girl and told her she was being moved for her protection. She got into a car with them and was never seen alive again. Her body was recovered from a graveyard and an autopsy showed she had been shot 12 times. Without this witness, there was no case against the slavers.

However, Colosimo's greatest enemy was the very man he depended on. The Prohibition of January 1920 made Colosimo and Torrio wealthier than ever, and Colosimo's Café alone brought in $50,000 a month between gourmet food and high-quality smuggled booze. Torrio wanted the Outfit to set up it's own hidden breweries and distilleries as a more cost-effective supply of alcohol. He also wanted to smuggle quality rye whisky from Canada rather than purchasing Canadian whisky from middlemen. However, Colosimo overruled him. He was wealthy enough already and didn't see the need to take risks setting up new rackets. Colosimo had only ever sold drink in speakeasies, and felt that becoming a wholesale supplier would attract too much attention from the Prohibition agents.

Colosimo angered Torrio further in 1921 when he divorced Torrio's Aunt Victoria. "Big Jim" had fallen in love with Dale Winter, a 19 year-old singer at Colosimo's Café, and the two were married in April 1921. Shortly after they returned from their honeymoon in Indiana, men in the Outfit began talking about "Diamond Jim". While his previous wife had understood and even taken part in Colosimo's criminal lifestyle, Dale wanted nothing to do with it. Colosimo spent very little time associating with his men, and left them to earn his money while he stayed at home with Dale and his new mother-in-law. At a meeting with the heads of all the major New York gangs, Torrio announced that he would be getting rid of Colosimo, and asked them to support his elevation to the position of boss in the Outfit.

On Tuesday, May 11, Torrio called Colosimo and asked him to come to the Café. Some bootleggers were delivering two shipments of whisky and wanted to give them personally to Colosimo. Despite "Big Jim's" objections, Johnny told him to be there at 4pm sharp. Colosimo's chauffeur collected him at 3:45 and later gave evidence that the boss was furious that Torrio couldn't deal with the bootleggers himself. During the ride to the Café, he sat in the back seat of the car muttering angrily in Italian. At the restaurant, he waited and spoke to the head chef, a man named Caesarino about changes to the menu. When it was obvious that the bootleggers were running late, he complained to his secretary Frank Camilla. Colosimo was worried and confused when Camilla informed him that there were no whisky deliveries due that day. The boss immediately phoned his lawyer, Rocco De Stefano but could not get through to him.

Next, Colosimo went back out to the restaurant floor and asked his bartender "Big Jim" O'Leary about the whisky. O'Leary knew nothing about it and Colosimo became even more upset. He left the restaurant at 4:25, but was shot twice by an assassin hiding in the cloakroom and firing a .38 calibre revolver. The only witness to the murder was a waiter who saw the killer jump out of the cloakroom, steal Colosimo's wallet and rush out the door. The waiter later told police that the killer had been eating ice-cream and drinking apricot brandy in the restaurant when "Big Jim" first arrived. On the check, he wrote "So long Vampire, so long Lefty." The meaning of this message has never been deciphered.

With the murder occurring so soon after Colosimo's divorce and remarriage, the police suspected the motive for the killing was revenge for the ill-treatment of his ex-wife Victoria. Victoria's brother Joe Moresco was the prime suspect, but he had an airtight alibi. Victoria, who had been in Los Angeles with her new husband was also suspected of arranging the killing. In all 30 people were interviewed by the police, including Johnny Torrio and Dale Colosimo.

Meanwhile, the waiter who witnessed the murder picked out a mugshot of Francesco Iole aka "Frankie Yale". Yale was Torrio's lieutenant in Brooklyn and was given all Torrio's New York interests when his boss went to Chicago. An unknown informant told investigators that Torrio paid Yale $10,000 after the murder, but that story was never confirmed. Yale, who was in Chicago at the time of the murder, was arrested and picked out of a police line-up by the waiter. However, the witness refused to testify and the New York mobster was released.

Years later, doubt was cast over Yale's guilt when Al Capone allegedly confessed to the murder of Colosimo during a conversation with Charles Mac Arthur, a journalist well known for his associations with mobsters. In Brooklyn, Capone worked for Torrio and then Yale, before joining Torrio in Chicago. Perhaps Capone did murder Colosimo, but this does not explain why the waiter fingered Yale, or what Yale was doing in Chicago at the time. It is also possible that Capone wanted to take credit for the slaying, or that Mac Arthur fabricated the confession.

The final mystery surrounding the murder is to do with Colosimo's estate. His lawyers expected to find $500,000 in cash and a fortune in bonds and jewellery. But the money, bonds and jewellery found added up to a total of $76,394, leaving his wife Dale baffled as to the whereabouts of the larger portion of her inheritance.

Despite the disappearance of his money, Colosimo's funeral was nothing short of extravagant. The procession was lead by 53 pall-bearers with judges and congressmen among their ranks. Over 1000 members of the Democrat Party marched to the tune of two brass bands. The Archbishop Charles Mundelein forbid a Catholic burial on the grounds that Colosimo was a "public sinner" because he divorced Victoria and married Dale. Evidently, the Archbishop believed that violating his original wedding vows was the worst of his crimes. Despite this, alderman "Bathhouse" John Coughlin recited the funeral prayers and "Diamond Jim" Colosimo was buried at Oak Woods cemetery in Chicago.


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