5 – Giacomo Colosimo
Also known as ‘Big Jim’ or ‘Diamond Jim,’ Giacomo Colosimo was born in Calabria, Italy on February 16, 1878. He moved to America in 1895 and began by trying to earn an honest living. He shined shoes and sold newspapers but soon decided that petty crime such as pickpocketing was more to his liking. He opened a brothel with his wife in 1902, and most sources suggest that he became the leader of a gang called the Chicago Outfit at around this time. He was also involved with an Italian gang called the Black Hand.
While Colosimo worked legitimately as a street sweeper and then a foreman, his illegal activities were bringing in real money. His brothel was a huge success and attracted the attention of two key politicians in the city. With their assistance, he soon rose to prominence in the underworld and ran up to 200 brothels. He was also involved in racketeering and gambling.
Despite his power, Colosimo was still threatened by the Black Hand gang who threatened to kill him if he didn’t give them money. Colosimo was frightened and paid up, but the gang continued to extort money. He turned to his nephew, Johnny Torrio, for assistance and Torrio murdered the Black Hand members that turned up to collect the next payment. Torrio continued to take care of his boss’ problems, but the two men soon fell out when the Prohibition era started. While Torrio wanted to make money from selling illegal booze, Colosimo didn’t want to draw attention to his many businesses.
The relationship between them completely fell apart when Colosimo divorced Torrio’s aunt and married a 19-year old singer in 1920. Torrio was irate and decided to kill his one-time boss. On May 11, 1920, Torrio arranged a meeting with Colosimo regarding a bootlegging shipment to one of Big Jim’s restaurants. Once Colosimo arrived and realized there was no shipment, he turned around to leave but was shot dead by a gunman hiding in a coatroom. Frankie Yale is widely believed to be the killer though some historians believe it was Al Capone. Torrio took control of the Outfit and eventually handed over the reins to Capone.