Benjamin Fein was born on the Lower East Side of New York City in 1889. He was troubled by a medical condition that caused his eyes to appear half shut, earning him the nickname “Dopey.” In reality, Benny was anything but dopey. After spending his youth as a pickpocket and a thief, he became one of the preeminent gang leaders of early 20th century New York. In 1910, fresh out of Elmira Reformatory, a prison in upstate New York, Dopey Benny joined Big Jack Zelig’s gang of labor sluggers, and rose quickly up the ranks to lead his own gang. (While most labor sluggers hired themselves out to either side during labor strikes, Benny’s gang allegedly worked only for the unions.)

In 1914, Benny was arrested for extortion. He expected to be bailed out by the unions, as he always was, but instead they let Benny languish in jail. He decided to name names, and as a result of Dopey Benny’s confession, over 30 union officials and gangsters were indicted on corruption charges. Upon his release from prison in 1917, Benjamin Fein entered the garment industry as a legitimate businessman. However, Fein made two more appearances in the criminal justice system. In 1931, he faced assault charges for dousing a business associate with acid. In 1941, he and Abraham Cohen were convicted as the ringleaders of an operation that allegedly stole over $250 million in garments over the span of three years. Upon his release from prison, he returned to the garment industry. He died in 1962 of lung disease.

Artwork Information: George Weinberg, 2009 Mixed Media Silkscreen on Paper 19" x 29"

Filed Under: Celebrity Arrests