Often considered the pioneer of labor racketeering, “Dopey” Benny turned gang violence into a business in New York’s garment district.
The Nickname: He earned the moniker “Dopey” not because of his intelligence, but due to a medical condition that caused his eyelids to droop halfway.
The Crimes: With a record dating back to 1900, he was arrested over 30 times for charges ranging from petty theft to murder. He was a hired muscle for unions, terrorizing non-union workers and employers alike.
Prison Time: Unlike many who avoided jail, Fein served several stints, including a 3.5-year sentence in Sing Sing prison for armed robbery.
Retirement: After a 1914 arrest where his political connections failed to protect him, he eventually retired from the underworld in 1917 to become a legitimate businessman.