Leo was so impressed with Vito's fighting ability that he accepted him into his circle as a fighter along with his bodyguard, Pepé Costa. It is here that Leo first met Vito Scaletta, after a confrontation between Vito and Brian O'Neill in the prison yard. His cell was a suite, complete with cooking facilities, and he was able to do as he pleases, which included the ability to instruct the guards to do favors for him. Due to his status and connections, Leo continued to live an entitled lifestyle while in prison. He was arrested for bookmaking and fixing fights in 1943 and sentenced to five years in Hartmann Federal Penitentiary.
Leo currently resides in a large mansion in Highbrook, Empire Bay. In 1933 he conspired with Carlo Falcone to assassinate Tomaso Moretti, bringing an end to the Vinci-Moretti War and the Moretti crime family. Later Leo ran the city's biggest bookmaking operation for 20 years. He used to fight in bare knuckle matches before becoming a prize-fighter. Leo's passion lies in sports, especially boxing and horse racing. In the early 1920s the pair took control of the Southport docks, which made for easy smuggling of alcohol during Prohibition. Upon their arrival from Sicily in 1908, the pair set up the family with Leo strategizing and Frank provided the muscle. Leo is consigliere to Frank Vinci and the mastermind behind the Vinci Crime Family, the most successful criminal organization in Empire Bay's history.
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