Born on December 16, 1907 in Chicago, Fiore “Fifi” Buccieri came of age during a time when Prohibition was fueling organized crime across America. He became active in the 1920s as a member of the notorious Chicago 42 Gang, which included future mob heavyweight Sam “Momo” Giancana. Buccieri was also the brother of fellow mobster Frank Buccieri.

By the mid-1920s, Fiore was already crossing paths with Al Capone, working as a gunman for the Outfit during the era’s violent bootleg wars. His first recorded arrest—on a concealed weapons charge—came in 1925, laying the groundwork for decades of underworld infamy. Accounts suggest that he may have been involved in as many as ten gangland slayings during this period, though specific cases remain unclear. Over the years, he evolved into a top enforcer for the Outfit, specializing in loansharking, labor racketeering, and acts of arson and bombing.

Buccieri’s methods were brutal. He and his associates would stake out employment offices and pass out business cards advertising him as a “loan officer.” The unemployed were easy prey—forced to steal or rob just to make payments. Buccieri would even deliver ominous warnings to friends of his “juice” victims: stay away from that person because “he is going to get hit.” Usually, people took the hint and paid up quickly.

One of Buccieri’s most infamous acts involved the gruesome murder of fellow loanshark William “Action” Jackson. The Outfit suspected Jackson of skimming money and working as an FBI informant. In one of Chicago’s most horrific mob killings, Jackson was tortured for days—impaled on a meat hook, beaten, burned, and prodded with cattle prods—until he died of shock. Buccieri, along with Jackie “The Lackey” Cerone, James “Turk” Torello, Sam “Mad Sam” DeStefano, and Dave Yaras, participated in the killing. Federal authorities later gained insight into the slaying from overheard conversations. 

By 1966 Buccieri had become a chief feared enforcer within the Outfit, labeled by federal agents as “the lord high executioner.” That same year, his 62nd birthday drew hundreds of mobsters nationwide—observed closely by law enforcement, theorized to be a clandestine summit for leadership transitions within the Outfit. On August 17, 1973, Fiore “Fifi” Buccieri died of cancer.