Bio: Benjamin Fein ‘Dopey Benny’ Labor Racketeer

Benjamin Fein, also known as ‘Dopey Benny’ was born in New York City circa 1889.  His varied criminal ‘career’ began in childhood,and he later went on to control New York’s labor racketeering at a fairly young age during the 1910s.

Fein was born into a Jewish family and grew up in a working class neighborhood on the Lower East Side, on the southeastern part of Manhattan. This impoverished district is where he honed his trade, becoming a pickpocket and sneak thief as a child. He possessed many talents, and by 1905 he had organized and formed his own gang of thieves. However, he was not indomitable and found himself at the Elmira Reformatory several times over the following five years – and during this time he also served in excess of three years for armed robbery. 

Following his release in 1910, Fein connected with ‘Big’ Jack Zelig’s gang, and it was during this time that he matured from thug to visionary. He quickly became involved in labor unions, extortion and the Garment District in New York.

Leader Jack Zelig was shot behind the ear and killed in October 2012, whilst riding on a trolley car passing East 13th Street. Following his death, the gang leadership was wide open and seemingly fell into Fein’s lap. 

In 1912 two major gangs, one led by Benjamin Fein and another by Joe ‘The Greaser’ Rosenzweig, dominated labor slugging in New York. Numerous remaining gangs, who had mostly been rendered powerless by Fein and Rosenzweig’s brutal tactics, united in a loose alliance in an attempt to break the monopoly held by the two gang leaders. This culminated in a major shootout, which took place on Grand Street and Forsyth Street in Manhattan. The gunfight raged for several hours though, surprisingly, very few casualties resulted from this battle. 

After his arrest on extortion and 2nd degree assault charges in 1914, Fein agreed to testify against several gang members involved in labor slugging –  his political connections and union officials had refused to come to his aid to bail him out and he’d been left to face the consequences. This resulted in charges being brought against 21 union officials and 11 gang members, however none actually made it to trial. 1914 was turning into an unlucky year for Fein. He was arrested for a second time on suspicion of killing a court clerk who was caught in the crossfire of a gunfight near St Mark’s Place, 8th Street. Fein’s luck changed however when he was released because none of the witnesses could identify him at the scene. 

The following year, Fein was arrested yet again. This time he was convicted on a murder charge that was related to labor slugging. He was released two years later.  

Following his release in 1917, Fein’s power and influence was in serious decline. He was still involved in his usual enterprises, though he stayed mainly in the background with less responsibilities. Maybe this was down to the fact that he had ‘named names’ and testified a few years prior. 

He was largely off the radar until July 1931, when he appeared in court, along with two others, on felonious assault charges. They had allegedly thrown acid over a local businessman by the name of Mortimer Kahn. This was Fein’s first appearance in court for thirteen years. 

It was another decade before Fein faced the courts again. He was taken into custody following a raid by police. They found a recently stolen garment shipment valued at $10,000. He was arrested along with mobsters Abraham Cohen, John Ferraro and two businessmen, Herman Fogel and Samuel Klein. Fein and Cohen were cited as the ringleaders of a criminal gang that took in an estimated $250,000 over a three-year timescale by raiding the city’s garment industry. 

Fein was spared a mandatory life sentence – which was the usual tariff for fourth-time offenders. He instead received a reduced sentence of ten to twenty years. 

After his release he returned to the garment industry, though this time he took the lawful route and became a tailor. 

It’s said he earned the nickname ‘Dopey Benny’ from a medical condition that caused his eyes to droop or appear half-closed.

Benny Fein died from natural causes on July 23, 1962, at the age of 75. His cause of death is stated as emphysema in ‘The Jews of Sing Sing’ (Ron Arons, Barricade Books, 2008) View On Amazon

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