Giacomo “Big Jim” Colosimo – Boss of the Chicago Outfit and Brothel Empire


Giacomo “Big Jim” Colosimo was an Italian immigrant Mafioso who got his start as a pickpocket and went on to build the Chicago Outfit, that city’s version of the American mob. He did it by pulling together a coalition of street thugs, pimps and extortionists to build a racket that has dominated organized crime in the Windy City for a century.

Colosimo’s success made possible the rise of bootlegging, which turned Chicago into a criminal’s paradise and, ironically, sealed his doom. He also gave birth to the careers of such future Mafia leaders as Johnny Torrio and Al Capone.

Colosimo was born on February 16, 1878, to Luigi and Giuseppina Colosimo in the small Italian town of Colosimi. The family emigrated to Chicago in 1895, when Giacomo was 17, and settled in the First Ward, a famously corrupt district that encompassed the city’s downtown. He took the name James after arriving.

Colosimo started his American life selling newspapers and shining shoes, but he soon moved on to petty thievery. Before long he rose in the criminal world and began organizing prostitutes. It was his work as a pimp that introduced him to his wife, a madame named  Victoria Moresco. They married in 1902 and opened a brothel together.

He also engaged in a uniquely Italian extortion scheme known as the Black Hand. Criminal immigrants targeted residents with threats of violence unless large sums of money were paid. Extortion letters were stamped with a hand in ink, giving the racket its name. This exposed Colosimo to a relatively organized part of the Chicago underworld, since Black Hands sometimes worked together.

Colosimo also got a legitimate job on the side. He worked alongside fellow Italian immigrants as a street sweeper and rose to become a foreman. He organized his co-workers into a social club that gave him even more influence among both his fellow immigrants and his fellow hoods. He also opened a pool hall that became a center of activity for street gangsters.

His brothel business was wildly successful and soon brought the attention of two key Chicago politicians, First Ward aldermen “Bathhouse” John Coughlin and Michael “Hinky Dink” Kenna. The two men, among the most corrupt in Chicago’s long history of political chicanery, controlled the city’s houses of prostitution. They first hired Colosimo as a Democratic Party precinct captain, then used him as a bagman.

Within a few years, Colosimo ran a network of 200 brothels and had his hands in gambling and other forms of racketeering. He was known as “Big Jim,” but his flashy dress and notoriety earned him another nickname that demonstrated his growing power: “Diamond Jim.”

Colosimo was now in charge of much of Chicago’s underworld, leading an organization that became known simply as the Outfit. The syndicate he created survives to this day and still bears his stamp. Though considerably weakened from its heyday, it continues to derive much of its income from gambling, as it did in his day.

But prostitution was always the center of Colosimo’s empire. At its peak, he even established a violent sex trafficking ring, known at the time as white slavery. Young immigrant women, often under age, were lured to Chicago with job offers, kidnapped, imprisoned, raped and sold to brothels or out-of-state pimps.

Colosimo’s power did not, however, fully protect him from his fellow Italian-American criminals. In fact it made him a target. In 1909 he received a Black Hand letter demanding money. Fearing for his life, he paid the extortionists. But this emboldened them, and they sent more letters.

Desperate for muscle to protect him, Colosimo turned to his wife’s nephew, Giovanni “Pappa Johnny” Torrio, a New York hood. Torrio owned a Brooklyn billiards hall that served as the gathering place for a criminal gang. Among the mobsters he had taken under his wing was Alphonse “Scarface” Capone, better known as Al.

Johnny Torrio came to Chicago to help his uncle and became his second in command. The two consolidated the

Giacomo “Big Jim” Colosimo with Giovanni “Pappa Johnny” Torrio

prostitution and gambling rackets and turned the Outfit into a criminal machine. Torrio also handled his boss’s extortion problem, murdering the Black Hands when they arrived to pick up what they thought was Colosimo’s latest payoff at a Chicago street corner.

By now Colosimo was one of the biggest names in the city. He had connections throughout the political world and owned a restaurant that attracted the rich and famous. Torrio kept the heat off, taking care of further extortionists and arranging the murder of a young woman who escaped Colosimo’s white slavery ring and threatened to testify against him.

But Colosimo and his underboss didn’t see eye to eye on the biggest criminal opportunity of the day, and their disagreement led to his downfall. Prohibition arrived in 1919, sending the distribution and sale of liquor into the hands of criminals. It was a perfect opportunity for the Outfit to make a fortune.

Colosimo, however, already made thousands on illegal alcohol from his restaurant and saw no need to risk federal attention by expanding further into bootlegging. This infuriated Torrio. Things got worse in 1921, when Colosimo divorced Torrio’s aunt, Victoria, and married a 19-year-old singer.

Torrio responded by putting a hit on Big Jim. At a meeting with leaders of the New York Mafia, Torrio asked for their support in making him the new boss of the Outfit once Colosimo was dead.

On May 11, 1920, Torrio called Colosimo and sent him to his restaurant to meet a supposed bootleg shipment. When Colosimo realized no shipment was coming, he became agitated and left. On his way out the door, he was shot dead by a gunman hiding in the coatroom. The assassin was never caught, though Frankie Yale has long been suspected.

A coroner depicting how Colosimo may have been shot.

Torrio quickly took the reins of the Outfit and built a massive network of speakeasies and liquor distribution. A few years later, after an attempt on his life, he handed the syndicate over to Capone, who built it into a genuine criminal empire.

Big Jim Colosimo left a major mark on Chicago, and the city rewarded him with a lavish funeral. There were 53 pallbearers, including congressmen and judges, and more than 1,000 members of the Democratic Party attended. The Catholic Church forbade burial on consecrated ground, not because of Big Jim’s crimes but because of his divorce.