Castellammarese War
During Prohibition, Strollo gained a formidable reputation as a bootlegger and hitman. In the early to mid-1920s, Strollo worked for gang boss Giuseppe "Joe the Boss" Masseria. After the Castellammarese War began in 1931, Strollo defected to Masseria's rival, Salvatore Maranzano, and became a trusted lieutenant and gunman.