Pennino started of as a member of Vincent's crew in Little Italy like Frankie and Anthony, posing as Vincent's personal bodyguard. He later helped to assassinate Joey Zasa by luring off his right-hand man Anthony Squigliaro by scratching up a fancy car that would be used in a raffle, using the keys to forge a line into the vehicle.
During the performance of Cavalleria rusticana in the Teatro Massimo in Sicily, Pennino was head of security, who reported the death of The Twins to Vincent. He also told him that they would have to leave immediately, for in a few minutes, carabinieri would be crawling all over the place. He became a caporegime once Vincent became Don in the same year and took over Vincent's old crew.