James Colosimo

Vincenzo Colosimo (; February 16, 1878 – May 11, 1920), known as James "Big Jim" Colosimo or as "Diamond Jim", was an Italian-American Mafia crime 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 heading a chain of brothels. From 1902 until his death in 1920, he led a gang known after his death as the Chicago Outfit. Colosimo was assassinated on May 11, 1920, and no one was ever charged with his murder. Johnny Torrio, an enforcer whom Colosimo imported in 1909 from New York, seized control of Colosimo's businesses after his death. Al Capone, a close associate of Torrio, has been accused of involvement in Colosimo's murder but was not yet in Chicago at the time. He emigrated from Italy to the US at the age of 17, starting out as a street sweeper in the First Ward. Colosimo's successful efforts to unionize the ward's street sweepers attracted the attention of First Ward aldermen Michael "Hinky Dink" Kenna and John Coughlin. They made him a precinct captain and street inspector. This gave Colosimo the political connections that helped him rise to power as a mob boss.

Prostitution empire In 1902, Colosimo married Victoria Moresco, an established Chicago madam and together they began expanding their prostitution business. The First Ward aldermen made Colosimo their bagman for collecting all vice related payoffs in their district. and The Saratoga, at Dearborn and 22nd Street. A month later, he and singer Dale Winter, the star attraction at his club, eloped to West Baden Springs, Indiana. Upon their return, he bought a home on the South Side. 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.

Colosimo was a 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.

Colosimo was interred at Oak Woods Cemetery in Chicago, in a lavish funeral witnessed by 5,000 mourners. His pall bearers, actual and honorary, included three judges, eight aldermen, a congressman, and several ward bosses.

In popular media Film In Scarface: The Shame of a Nation (1932), the death of "Big Louie" Costillo (Harry J. Vejar) is loosely based on Colosimo's assassination. Antonio "Tony" Camonte kills Big Louie at the behest of his friend Johnny Lovo, Costillo's right-hand man. Lovo was based on Johnny Torrio and Camonte on Al Capone, and the film presents Costillo's murder as the beginning of Lovo and Camonte's involvement in bootlegging, similar to how Colosimo's refusal to allow bootlegging is considered the primary reason for his murder. Joe De Santis played Colosimo in Al Capone (1959). Frank Campanella played Colosimo in Capone (1975).

Television Peter Siragusa portrayed Colosimo in the pilot episode of The Untouchables (1993). 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. Colosimo was portrayed by Peter Banks in a 1994 episode of In Suspicious Circumstances, titled No Witness, No Case (a reference to a prostitute whom Colosimo had sent from Chicago to Connecticut, who was murdered after she talked to the police). 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 to go into bootlegging. He is shown being shot at the back of the head while listening to an Enrico Caruso record in his restaurant. He was portrayed by Andre King in the 2016 docuseries The Making of the Mob: Chicago.

Music In Ian Hunter's song "Resurrection Mary" (on The Artful Dodger), the storyteller, who sees the infamous ghost of the title, used to do "the numbers for Big Jim." Kool G Rap makes a reference to Colosimo in the song "Guns Blazing (Drums of Death Pt. 1)" by UNKLE on the 1998 album Psyence Fiction.

Theater

In the musical Chicago, the character Velma Kelly mentions she wants to perform at Big Jim Colosimo's, bribing the matron for the opportunity.

Gaming In Mafia: Definitive Edition (2020), the mentioned offscreen murder of the Illinois mob boss Felice Peppone in 1922, by his two capos Ennio Salieri and Marcu Morello to get into the bootlegging business and form their own Mafia families in the city of Lost Heaven, is loosely inspired by the murder of Colosimo.