Vincenzo Colosimo (; February 16, 1878 – May 11, 1920), known as James "Big Jim" Colosimo or as "Diamond Jim", was an

Italian-American Mafia The American Mafia, commonly referred to in North America as the Italian American Mafia, the Mafia, or the Mob, is a highly organized Italian American criminal society and organized crime group. The organization is often referred to by its mem ...

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 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 The Chicago Outfit (also known as the Outfit, the Chicago Mafia, the Chicago Mob, the Chicago crime family, the South Side Gang or The Organization) is an Italian-American organized crime syndicate or crime family based in Chicago, Illinois, ...

. Colosimo was assassinated on May 11, 1920, and no one was ever charged with his murder.

Johnny Torrio John Donato Torrio (born Donato Torrio, ; January 20, 1882 – April 16, 1957) was an Italian born-American mobster who helped build the Chicago Outfit in the 1920s later inherited by his protégé Al Capone. Torrio proposed a National Crime Sy ...

, 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.

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 A precinct captain, also known as a precinct chairman, precinct delegate, precinct committee officer or precinct committeeman, is an elected official in the American political party system. The office establishes a direct link between a political ...

and later their

bagman The term bagman (or bag man) has different meanings in different countries. One group of definitions centers on the idea of traveling. In British usage, "bagman" is a term for a traveling salesman, first known from 1808. In Australian usage, ...

. This gave Colosimo the political connections that helped him in his rise to power as a mob boss.''Capone: The Life and World of Al Capone'' by John Kobler

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 madam and together they opened a second brothel. Torrio was the nephew of Moresco. According to Laurence Bergreen, "Torrio is lsodescribed 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. Among his first brothels were The Victoria, on Armour Avenue (named in honor of his wife) and The Saratoga, at Dearborn and 22nd Street. Within a few years, Colosimo had expanded this to nearly 200 brothels and had also made inroads into

gambling Gambling (also known as betting or gaming) is the wagering of something of value ("the stakes") on a random event with the intent of winning something else of value, where instances of strategy are discounted. Gambling thus requires three el ...

and racketeering. Colosimo was reputedly making $50,000 ($ 720 000 in 2022) per month from his various legal and illegal operations.

Help from New York

By 1909,

Black Hand Black Hand or The Black Hand may refer to: Extortionists and underground groups * Black Hand (anarchism) (''La Mano Negra''), a presumed secret, anarchist organization based in the Andalusian region of Spain during the early 1880s * Black Hand (e ...

extortion was a serious threat to Colosimo in Chicago. He brought in gangster John "The Fox" Torrio from

Brooklyn Brooklyn () is a borough of New York City, coextensive with Kings County, in the U.S. state of New York. Kings County is the most populous county in the State of New York, and the second-most densely populated county in the United States, be ...

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 A bouncer (also known as a doorman or door supervisor) is a type of security guard, employed at venues such as bars, nightclubs, cabaret clubs, stripclubs, casinos, hotels, billiard halls, restaurants, sporting events, schools, concerts, or ...

, which gave Capone his entry into Chicago crime.

Betrayal

Grave of Vincenzo Colosimo (1878–1920) at Oak Woods Cemetery, Chicago

When

Prohibition Prohibition is the act or practice of forbidding something by law; more particularly the term refers to the banning of the manufacture, storage (whether in barrels or in bottles), transportation, sale, possession, and consumption of alcohol ...

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 West Baden Springs is a town in French Lick Township, Orange County, in the U.S. state of Indiana. The population was 574 at the 2010 census. It is well known for its West Baden Springs Hotel and for being the birthplace of Larry Bird. Histor ...

. 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 Francesco Ioele (; January 22, 1893 – July 1, 1928), known as Frankie Yale or Frankie Uale, was an Italian-American gangster based in Brooklyn and second employer of Al Capone. Early life Yale was born in Longobucco, Italy, on January 22, ...

had allegedly traveled from New York to Chicago and personally killed longtime gang boss Colosimo at the behest of Torrio and Capone. Although suspected by Chicago police, Yale was never officially charged.Schoenberg, pgs. 62-65 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. Colosimo was interred at Oak Woods Cemetery in Chicago, witnessed by 5,000 mourners.

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. Big Louie is killed by Antonio "Tony" Camonte 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 Joseph Vito Marcello De Santis (June 15, 1909 – August 30, 1989) was an American radio, television, movie and theatrical actor and sculptor. Biography Joe De Santis was born Joseph Vito Marcello De Santis to Italian immigrant parents in Ne ...

played Colosimo in '' Al Capone'' (1959). * Frank Campanella played Colosimo in '' Capone'' (1975).

Television

*Colosimo was portrayed by Peter Siragusa 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 ''The Young Indiana Jones Chronicles'' is an American television series that aired on ABC from March 4, 1992, to July 24, 1993. Filming took place in various locations around the world, with "Old Indy" bookend segments filmed in Wilmington, Nort ...

'', 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 Jane Krakowski (; ; born October 11, 1968) is an American actress, comedienne, and singer. She is best known for her starring role as Jenna Maroney in the NBC satirical comedy series ''30 Rock'' (2006–2013, 2020), for which she received four ...

. *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

to allow Torrio to go into bootlegging. * He was portrayed by Andre King in the 2016 docuseries '' The Making of the Mob: Chicago.''

Music

*In Ian Hunter’s song "Resurrection Mary", the story-teller, who sees the infamous ghost of the title, used to do "the numbers for Big Jim."