Ah, let me tell ya ’bout Big Jim Colosimo, the kingpin of Chicago’s underworld, born Vincenzo Colosimo on February 16, 1878, in Calabria, Italy. This guy, known as “Diamond Jim” for his flashy style and diamond-studded attire, started his American dream with small-time crimes, workin’ his way up to runnin’ nearly 200 brothels, rakin’ in fifty grand a month, which today would be like swimming in millions.
He cozied up to the First Ward’s political big shots, Hinky Dink and Bathhouse John, and before you knew it, he was their bagman, and later, a major mob boss. Colosimo wasn’t just a thug; he was a showman, opening the famed Colosimo’s Cafe in 1910, a joint at 2126 South Wabash that became the hotspot for Chicago’s elite. This joint wasn’t just a cafe; it was a slice of the high life, where the booze flowed and the music played, and everyone from the city’s upper crust to the most notorious gangsters came to unwind.
But Big Jim had a soft spot for the ladies and the good life, which made him hesitant to dive into the bootlegging biz when Prohibition hit. His stubbornness and a messy divorce from madam Victoria Moresco, followed by a quick marriage to singer Dale Winter, left him vulnerable.
On May 11, 1920, the party ended when he strolled into his beloved cafe, only to catch a bullet behind the ear from a gunman lurking in the cloakroom, rumored to be Frankie Yale, likely on orders from his own protégé, Johnny Torrio. They said he got whacked for not wanting to jump into the bootlegging game, with Torrio and Al Capone takin’ over his empire, laying the groundwork for the notorious Chicago Outfit. Big Jim’s reign ended in a pool of blood, but his legend lives on as the original architect of organized crime in the Windy City.
