Vincenzo Colosimo, known as James "Big Jim" Colosimo or as "Diamond Jim", was an Italian-American Mafiacrime boss who emigrated from Calabria, Italy, in 1895, and built a criminal empire in Chicago based on prostitution, gambling, and racketeering. He gained power through petty crime and by heading a chain of brothels. From about 1902 until his death in 1920, he led a gang that became known after his death as the Chicago Outfit. Johnny Torrio was an enforcer whom Colosimo imported in 1909 from New York and who seized control after his death. Al Capone, a Torrio henchman, allegedly was directly involved in the murder.
Early years
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. 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 in his rise to power as a mob boss.
Prostitution empire
Later, Colosimo acquired another nickname, "Diamond Jim," because he frequently dressed in a white suit and wore diamond pins, rings, and other jewelry. This, combined with his personal charm and money, helped him establish relationships with women. He had a love of both women and money, which fueled his enthusiasm for prostitution. In 1902, Colosimo married Victoria Moresco, an established Chicago madame, and together they opened a second brothel. Torrio was the nephew of Moresco. According to Laurence Bergreen, "Torrio is 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." Within a few years, Colosimo had expanded this to nearly 200 brothels and had also made inroads into gambling and racketeering. He was reputedly making $50,000 per month from his various legal and illegal operations.
Help from New York
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. 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. In 1919, Torrio and Colosimo opened a brothel at 2222 South Wabash called the Four Deuces, a reference to 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.
Betrayal
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. A month later, he and Dale Winter eloped to West Baden Springs, Indiana. Upon their return, he bought a home on the South Side. 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. Frankie Yale had allegedly traveled from New York to Chicago and personally killed longtime gang boss Colosimo at the behest of Chicago Outfit friends Torrio and Capone. Although suspected by Chicago police, Yale was never officially charged. Colosimo was allegedly murdered because he stood in the way of his gang making bootlegging profits, having "gone soft" after his marriage with Winter. Al Capone has also been suggested as the gunman. Colosimo's ex-wife, unhappy with the financial arrangements of the divorce, is also theorized having arranged the murder. Colosimo was the first gang leader to organize the disparate parts of Chicago's crime scene. After his death, Torrio took over his gang, later to be replaced by Al Capone. His mob eventually became the infamous Chicago Outfit that ruled over some parts of the city.
In the 1932 gangster movie Scarface: The Shame of a Nation, the death of "Big Louie" Costillo is loosely based on Colosimo's assassination. Big Louie is killed by the main characters Johnny Lovo and Antonio Camonte. Lovo was based on Johnny Torrio and Camonte on Al Capone, with Costillo's murder to allow them to begin bootlegging.
James Colosimo and a fictionalized account of his murder was the subject of a 1993 episode of The Young Indiana Jones Chronicles, titled "Young Indiana Jones and the Mystery of the Blues." Colosimo was portrayed by Raymond Serra, Victoria Moresco by Linda Lutz, and Dale Winter by Jane Krakowski.
In 2010, Colosimo's murder was depicted in the series premiere of HBO's Boardwalk Empire. It depicts Colosimo, played by Frank Crudele as the victim of a hit ordered by Torrio and committed by Frankie Yale to allow Torrio's gang to go into bootlegging.
