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Leo was born in Sicily and fled to America on the onset of World War  

ii.
Vito first meets him in jail.  Vito works with him while in jail and earns his friendship and respect.  Leo teaches Vito proper fighting techniques. He also teaches Vito about the inner workings of the three major families in Empire Bay.  
While in jail Leo operates a fight club, which he profits from by running bets.  The  other inmates speculate that illegal gambling is the reason why Leo is in jail in the first place.  
Even while in jail Leo continues to serve as consigliere to Don Vinci.  This position grants Leo extra luxuries in prison.  
Leo is let out of prison a few months before Vito, upon release he pulls some strings and gets Vito released 4 years early. 
Falcone calls out a hit on Leo, however Vito intervenes and helps Leo escape because he felt he owed Leo for all his help.  After this Leo skips town saying he wishes to retire to somewhere warm. 
Leo reappears by the end of the game with a final job for Vito.

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