Buried here lies Vincenzo Colosimo. But he was better known as “Big Jim” or “Diamond Jim”. We are standing at the James Big Jim Colosimo Grave. It marks the final resting place of a notorious figure.
James Big Jim Colosimo was an Italian-American Mafia boss. He built a criminal empire. It was based on prostitution, gambling, and racketeering. He emigrated from Calabria, Italy, in 1895.
Colosimo gained power through petty crime. He also headed a chain of brothels. From 1902 until his death in 1920 he led a gang. It later became known as the Chicago Outfit.
Born on February 16 1878 Colosimo’s early life was humble. At 17 he left Italy for Chicago. He quickly became involved in petty crime. His charisma caught the attention of local aldermen. Michael “Hinky Dink” Kenna and John Coughlin appointed him as a precinct captain. They later made him their bagman. This gave him the political connections. They helped him rise as a mob boss.
Colosimo loved women and money. This fueled his enthusiasm for prostitution. In 1902 he married Victoria Moresco. She was an established Chicago madam. Together they expanded their prostitution business.
Among Colosimo’s first brothels was The Victoria. It was named after his wife. Others included The Saratoga. Within a few years Colosimo had almost 200 brothels. He also made inroads into gambling and racketeering. Colosimo reputedly made $50000 per month. This equates to about $720000 today. It was from his various legal and illegal operations.
By 1909 Black Hand extortion threatened Colosimo in Chicago. He brought in John “The Fox” Torrio from Brooklyn. Torrio became his second in command. Torrio was also the nephew of Moresco.
In 1910 Colosimo opened Colosimo’s Cafe. It was a restaurant and nightclub. It quickly became a popular destination. Prominent Chicagoans and visitors frequented it. Colosimo’s crew grew into a multi-ethnic gang. It included Italian, Irish, Polish and Jewish gangsters. Colosimo’s vice interests expanded into Chicago’s suburbs.
In 1919 Torrio and Colosimo opened the Four Deuces. It was a brothel at 2222 South Wabash. Torrio hired Al Capone. He was an old Brooklyn colleague. Capone worked as a bartender and bouncer. This gave Capone his entry into Chicago crime.
When Prohibition began in 1920 Torrio wanted to enter bootlegging. But Colosimo refused. In March 1920 Colosimo divorced Moresco. A month later he married Dale Winter.
On May 11 1920 Colosimo drove to Colosimo’s Cafe. He was to meet an associate. But he was shot and killed by a gunman. The gunman hid in the cloak room. A bullet entered Colosimo’s brain.
Contract killer Frankie Yale allegedly killed Colosimo. He was acting at Torrio’s behest. Although suspected Yale was never charged. Colosimo was allegedly murdered. He stood in the way of bootlegging profits. He had “gone soft” after his marriage with Winter.
Colosimo was the first gang leader. He organized Chicago’s crime scene. After his death Torrio took over his gang. Later Al Capone replaced Torrio. His mob eventually became the Chicago Outfit.
Colosimo was interred here at Oak Woods Cemetery. His lavish funeral was witnessed by 5000 mourners. The James Big Jim Colosimo Grave is more than a marker. It represents a complex chapter in Chicago’s history. It is a time of ambition, violence, and the rise of organized crime.