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 terms Italian Mafia and Italian Mob apply t ...

crime boss who emigrated from

Calabria Calabria is a Regions of Italy, region in Southern Italy. It is a peninsula bordered by the region Basilicata to the north, the Ionian Sea to the east, the Strait of Messina to the southwest, which separates it from Sicily, and the Tyrrhenian S ...

, Italy, in 1895 and built a criminal empire in

Chicago Chicago is the List of municipalities in Illinois, most populous city in the U.S. state of Illinois and in the Midwestern United States. With a population of 2,746,388, as of the 2020 United States census, 2020 census, it is the List of Unite ...

based on prostitution, gambling and

racketeering Racketeering is a type of organized crime in which the perpetrators set up a coercion, coercive, fraud, fraudulent, extortionary, or otherwise illegal coordinated scheme or operation (a "racket") to repeatedly or consistently collect a profit. ...

. He gained power through petty crime and heading a chain of

brothel A brothel, strumpet house, bordello, bawdy house, ranch, house of ill repute, house of ill fame, or whorehouse is a place where people engage in Human sexual activity, sexual activity with prostitutes. For legal or cultural reasons, establis ...

s. From 1902 until his death in 1920, he led a gang 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 Americans, Italian American American Mafia, Mafia crime family based in Chicago, I ...

. 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 mobster who helped build the Chicago Outfit in the 1920s later inherited by his protégé Al Capone. Torrio proposed a National Crime Syndicate in ...

, an enforcer whom Colosimo imported in 1909 from New York, seized control of Colosimo's businesses after his death.

Al Capone Alphonse Gabriel Capone ( ; ; January 17, 1899 – January 25, 1947), sometimes known by the nickname "Scarface", was an American organized crime, gangster and businessman who attained notoriety during the Prohibition era as the co-foun ...

, 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 The province of Cosenza () is a province in the Calabria region of Italy. Its capital is the city of Cosenza. It contains 150 ''comuni'' (: ''comune''), listed at list of ''comuni'' of the province of Cosenza. The province of Cosenza contains ...

, 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 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, it ...

. This gave Colosimo the political connections that helped him 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 charm and money, helped him establish relationships with women. He loved women and money, which fueled his enthusiasm for

prostitution Prostitution is a type of sex work that involves engaging in sexual activity in exchange for payment. The definition of "sexual activity" varies, and is often defined as an activity requiring physical contact (e.g., sexual intercourse, no ...

. In 1902, Colosimo married Victoria Moresco, an established Chicago

madam Madam (), or madame ( or ), is a polite and formal form of address for Woman, women in the English language, often contracted to ma'am (pronounced in American English and this way but also in British English). The term derives from the French la ...

and together they began expanding their prostitution business. Among Colosimo's first brothels was The Victoria (named after his wife), on Archer and Armour Avenue, 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 (economics), value ("the stakes") on a Event (probability theory), random event with the intent of winning something else of value, where instances of strategy (ga ...

and

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

Help from New York and expansion

By 1909, Black Hand extortion was a serious threat to Colosimo in Chicago. He brought in gangster John "The Fox" Torrio from

Brooklyn Brooklyn is a Boroughs of New York City, borough of New York City located at the westernmost end of Long Island in the New York (state), State of New York. Formerly an independent city, the borough is coextensive with Kings County, one of twelv ...

and made him his second in command. Torrio was the nephew of Moresco. Laurence Bergreen states, "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. In 1910, Colosimo opened Colosimo's Cafe, a restaurant and nightclub at 2126 South Wabash. It quickly became a popular destination for prominent Chicagoans and visitors, gaining nationwide fame. Colosimo's crew grew into a multi-ethnic, hierarchical gang, with Italian, Irish, Polish, and Jewish gangsters. Colosimo's vice interests eventually expanded into Chicago's suburbs, including Burnham and South Chicago. 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

to work as a bartender and bouncer, which gave Capone his entry into Chicago crime.

Betrayal

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 alcoholic b ...

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 541 at the 2020 census. History West Baden Springs is located in the vicinity of several mineral springs. The town was founde ...

. Upon their return, he bought a home on the South Side. On May 11, 1920, Colosimo drove to Colosimo's Cafe to meet an associate he had never met before. He was shot and killed a few minutes after entering the restaurant by a gunman hiding in the cloak room. A bullet entered Colosimo's brain, behind his right ear. Contract killer

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

had allegedly traveled from New York to Chicago and personally killed longtime gang boss Colosimo at the behest of Torrio. 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. 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

. 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.

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 Joseph Vito Marcello De Santis (June 15, 1909 – August 30, 1989), known as Joe De Santis, was an American radio, television, movie and theatrical actor. Biography Joseph Vito Marcello De Santis was born to Italian immigrant parents in New ...

played Colosimo in ''

'' (1959). *

Frank Campanella Frank Campanella (March 12, 1919 – December 30, 2006) was an American actor. He appeared in numerous television series, as well as a few films and Broadway productions. Early life and career Campanella was born in New York City, the son of P ...

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 ''The Young Indiana Jones Chronicles'' (sometimes referred to as ''Young Indy'') 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" ...

'', 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 and singer. She starred as Jenna Maroney in the NBC satirical comedy series ''30 Rock'' (2006–2013, 2020), for which she received four Primetime Emmy Award nominations for Out ...

. *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 ''Boardwalk Empire'' is an American period crime drama television series created by Terence Winter for the premium cable channel HBO. The series is set chiefly in Atlantic City, New Jersey, during the Prohibition era of the 1920s. The series sta ...

''. 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 is shown being shot at the back of the head while listening to an

Enrico Caruso Enrico Caruso (, , ; 25 February 1873 – 2 August 1921) was an Italian operatic first lyric tenor then dramatic tenor. He sang to great acclaim at the major opera houses of Europe and the Americas, appearing in a wide variety of roles that r ...

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", the storyteller, who sees the infamous ghost of the title, used to do "the numbers for Big Jim."

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.