Born Vincenzo Colosimo on February 16th 1878, Big Jim was an Italian-American Mafia Crime Boss who emigrated from Calabria, Italy in 1895 to Chicago. He gained his power by running a chain of brothels as well as some petty crime, and he also led his own South-Side gang that was more famously known as ‘The Chicago Outfit‘.
He gained his nickname ‘Diamond Jim‘ due to his attire, he frequently dressed in all white suits, wore diamond pins, jewelry and rings, this gentleman dress sense earned him many relationships with women, and it was his love of women and money that fuelled his decision to start his brothel chain.
In 1902, Colosimo married Victoria Moresco, an established Chicago madame and together they opened a second brothel. Within a few years, Colosimo had expanded this to nearly 200 brothels and had also made money in the same ways many other gangsters did by gambling and racketeering.
By 1909, Black Hang extortion was a serious threat to Colosimo in Chicago, so he brought in gangster John ‘The Fox’ Torrio from Brooklyn and made him his second in command.
In 1910 he opened Colosimo’s Café, a restaurant and nightclub, it was quickly made a hotspot for locals and visitors to Chicago.
In 1919, Torrio and Colosimo opened another brothel and called it the Four Deuces, it was here where Al Capone made his entry into the Chicago underworld. Torrio had hired Capone as the bar tender and bouncer.
In 1920 prohibition hit the US, so Torrio pushed for the gang to enter into bootlegging, but Colosimo point blankly refused.
In May 1920, Colosimo left Chicago to marry his second wife, Dale Winter, having deserted Victoria Moresco. When he returned the following week, Torrio called and told him a shipment was about to arrive at his café.
Colosimo drove there to await it, but instead he was shot in an ambush and killed.
The initial suspect was his new wife Dale, but the murder officially went unsolved and no one was ever arrested or charged for it.
It is widely believed that Torrio had ordered the killing so that he could go into the business of bootlegging which he originally wanted to do. Allegedly Torrio brought in New York colleague Frankie Yale, to eliminate Colosimo, it was also suggested that Al Capone had played a part in the killing of Colosimo.
Soon after his death Torrio took over his gang.
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