Big Jim Colosimo

Colosimo was born on February 16, 1878, to Luigi Colosimo and his second wife Giuseppina Mascaro in the town of Colosimi, Province of Cosenza, Italy.[4] He emigrated from Italy to Chicago at the age of 17, starting out as a petty criminal. Colosimo attracted the attention of First Ward aldermen Michael "Hinky Dink" Kenna and John Coughlin. They made him a precinct captain and later their bagman. This gave Colosimo the political connections that helped him rise to power as a mob boss.[5]

Later, Colosimo acquired another nickname, "Diamond Jim," because he frequently dressed in a white suit and wore diamond pins, rings, and other jewelry.[4] This, combined with his charm and money, helped him establish relationships with women. He loved women and money, which fueled his enthusiasm for prostitution. In 1902, Colosimo married Victoria Moresco, an established Chicago madam[6] and together they opened a second brothel. Torrio was the nephew of Moresco. Laurence Bergreen states, "Torrio is [also] described as Colosimo's nephew, but in the absence of any evidence to confirm the relationship, it is more likely their kinship was spiritual rather than familial." There are also references to Colosimo's wife being somehow related to John Torrio.[3]

Among his first brothels were The Victoria, on Armour Avenue (named in honor of his wife)[7] and The Saratoga, at Dearborn and 22nd Street.[8] Within a few years, Colosimo had expanded this to nearly 200 brothels and had also made inroads into gambling and racketeering.[5] Colosimo was reputedly making $50,000 ($720,000 in 2022) per month from his various legal and illegal operations.[9]

By 1909, Black Hand extortion was a serious threat to Colosimo in Chicago. He brought in gangster John "The Fox" Torrio from Brooklyn and made him his second in command.[6] The following year, he opened Colosimo's Cafe, a restaurant and nightclub at 2126 South Wabash. It quickly became a popular destination for prominent Chicagoans and visitors to Chicago.[4] In 1919, Torrio and Colosimo opened a brothel at 2222 South Wabash called the Four Deuces, referencing the address. Torrio hired his old Brooklyn colleague Al Capone to work as a bartender and bouncer, which gave Capone his entry into Chicago crime.[5]

Al Capone mugshot

Colosimo mausoleum at Oak Woods Cemetery

When Prohibition went into effect in 1920, Torrio pushed for the gang to enter into bootlegging, but Colosimo stubbornly refused. In March 1920, Colosimo secured an uncontested divorce from Moresco.[9] A month later, he and Dale Winter eloped to West Baden Springs, Indiana. Upon their return, he bought a home on the South Side.[9] On May 11, 1920, Torrio called and told Colosimo that a shipment was about to arrive at his restaurant. Colosimo drove there to await it, but instead, he was shot in an ambush and killed.[10] Frankie Yale had allegedly traveled from New York to Chicago and personally killed longtime gang boss Colosimo at the behest of Torrio and Capone.[11] Although suspected by Chicago police, Yale was never officially charged.[12] Colosimo was allegedly murdered because he stood in the way of his gang making bootlegging profits, having "gone soft" after his marriage with Winter.[9] Al Capone has also been suggested as the gunman.[5] Colosimo's ex-wife, unhappy with the financial arrangements of the divorce, is also theorized to have arranged the murder.[9]

Colosimo was the first gang leader to organize the disparate parts of Chicago's crime scene. After his death, Torrio took over his gang,[1] later to be replaced by Al Capone.[6] His mob eventually became the infamous Chicago Outfit that ruled over some parts of the city.[5]

Colosimo was interred at Oak Woods Cemetery in Chicago, witnessed by 5,000 mourners.[3]

• List of organized crime killings in Illinois
• List of unsolved murders

• Bilek, Arthur J. The First Vice Lord: Big Jim Colosimo and the Ladies of the Levee. Nashville: Cumberland House, 2008.