12. Prohibition’s Biggest Grudge
Chicago mob boss Al Capone’s greatest grudge was against the North Side Gang, led by Dean O’Banion, Hymie Weiss, and George “Bugs” Moran. It took place against the backdrop of Prohibition, which had fueled organized crime and violence between criminals, as they competed for a slice of the increasingly lucrative illegal alcohol. Polish born Hymie Weiss (1898 – 1926) grew up in Chicago’s North Side, where he took to a life of crime in his early teens. He eventually teamed up with George “Bugs” Moran and Dean O’Banion to form the North Side Gang, which dominated crime in North Chicago during Prohibition.
Competition over illegal alcohol with the Chicago Outfit, led by Johnny Torrio and his chief lieutenant Al Capone, turned violent. The result was a bitter grudge that lasted for years, claimed multiple lives, and led to America’s most notorious mob massacre. When the competition with the North Side Gang heated up, Al Capone called in his former boss, Frankie Yale. Born Francisco Iole in Calabria in southern Italy, Yale had arrived in the US at age eight. As a teenager, he joined the Five Points Gang. He quickly developed a reputation as a ferocious fist fighter and brawler, and was first arrested in 1912 at age nineteen for disorderly conduct.
Yale began his organized crime career as a protection and extortion racketeer, and in 1913 he was arrested for the robbery and assault of a dry goods store. He walked after the store owner retracted his identification of the culprit. By 1917, he had invested his rackets proceeds into a bar in Coney Island, which became his base of operations. Yale became an early New York mafia leader and hitman, and employed a young Al Capone in his operations. Yale’s criminal enterprise typified a new trend in American Mafiosi “families”: the employment of Italians from all regions, and not just from the boss’ hometown or district as had been the case traditionally.
