 When the Volstead Act (National Prohibition Act of 1919) was enacted, Esposito's organization, the 42 Gang, which included Sam "Momo" Giancana and Paul "The Waiter" Ricca, quickly entered into bootlegging.Esposito's early success with the Genna Brothers may have been a factor in the 1920 murder of rival James "Big Jim" Colosimo, a long time racketeer who had been hesitant to begin his own bootlegging operations.By the early 1920s, Esposito had become a Republican ward boss of the 19th Ward in Chicago, one of the earliest Italian-Americans to be elected to this job.