On this day in 1878 Jim Colosimo was born in Colosimi, Italy. He was one of the Mustache Pete era crime bosses who headed what we now call the Chicago‬ Outfit. Big Jim built a successful empire and owned a chain of brothels.

The one move that would put Diamond Jim in the firing line was not pushing into the bootlegging of alcohol during early Prohibition, a move that would effectively put a contract on his head.

On this day, February 16, in 1878, Giacomo "Big Jim" Colosimo was born in Colosimi, a small town in the Calabria region of southern Italy. He would go on to become one of the most powerful and colourful underworld figures in early twentieth century America, laying the very foundations upon which the Chicago Outfit would eventually be built.

Colosimo arrived in Chicago around 1895 and quickly made himself useful in the city's political machinery, working as a street sweeper and eventually organising his fellow Italian immigrant labourers into a voting bloc that caught the attention of corrupt aldermen "Bathhouse" John Coughlin and Michael "Hinky Dink" Kenna. Their patronage gave Colosimo a foothold in the city's First Ward, and he used it shrewdly. By the early 1900s, he had established himself as the undisputed boss of Chicago's vice trade, running a sprawling network of brothels and gambling dens across the city. His flagship establishment, Colosimo's Café on South Wabash Avenue, became a glittering showpiece frequented by politicians, entertainers, and socialites, giving Big Jim a veneer of respectability that few men in his position ever managed to cultivate.

When the Black Hand began extorting him around 1909, Colosimo made a fateful decision that would change American organised crime forever. He summoned his nephew, a young New York fixer named Johnny Torrio, to help deal with the threat. Torrio proved ruthlessly effective, and the two men built an operation of remarkable sophistication. It was Torrio who would later bring a teenage Al Capone to Chicago, planting the seed for the empire that would follow.

Yet for all his cunning, Colosimo's downfall came from complacency. When Prohibition arrived in 1920, Torrio recognised immediately that bootlegging represented an almost incomprehensible opportunity for wealth and power. Big Jim, comfortable in his prosperity and distracted by a new romantic interest in a young singer named Dale Winter, showed little appetite for the risks involved. His reluctance to move into the liquor trade made him an obstacle rather than an asset, and on May 11, 1920, he was shot dead in the lobby of his own café. Torrio was widely suspected of ordering the hit, with a young Frankie Yale believed to have pulled the trigger.

Colosimo's legacy is that of an unwitting architect. He built the infrastructure, forged the political connections, and imported the talent that would eventually make Chicago the most notorious mob city in the world.