Joe Bruno on the Mob — Big Jack Zelig

Big Jack Zelig was born Zelig Harry Lefkowitz in New York City in 1888. He started his criminal career at the age of nine, and by the time he had reached thirteen and working for the Crazy Butch Gang on the Lower East Side, he became known as one of the best pickpockets in New York City. By the time he was fifteen, Zelig had become a member of the feared Monk Eastman Gang. As an Eastman, Zelig was respected on the Lower East Side as a feared street fighter, who was especially adept at using a knife. Because of his roughhouse escapades, he was dubbed by the police, “The Most Feared Man in New York City.”

With Eastman in jail for assault and robbery, the Eastman gang was headed by Max “Kid Twist” Zwerbach, who appointed Zelig his number one lieutenant. When Zwerbach was killed in 1908, reportedly by a member of the rival Five Points Gang, Zelig took control of his gang.

Zelig’s gang robbed casinos, bank and brothels, but their specialty was thuggery for hire. They even had a printed menu of the gang’s services. To have them slash the cheek of someone, it cost anywhere from $1 to $10, according to your ability to pay. A shot in the leg or arm cost $5 to $25. Tossing a live bomb to take down an establishment also cost $5 to $25. And to kill someone dead, they charged anywhere from $10 to $100. Zelig’s capable men included such notables as Harry “Gyp the Blood” Horowitz, “Waxey” Gordon, “Lefty” Louie Rosenberg and “Dago Frank” Cirofisi.

Zelig’s two chief nemeses, who were fighting with him behind the scenes for control of the former Eastman Gang, were gang members Chick Tricker and Jack Sirocco. They tricked Zelig into going on a back robbery with them, then left him behind to take the rap. Zelig was arrested and none to happy at his pals. Then to add insult to injury, Tricker and Sirocco refused to bail out Zelig, figuring with Zelig behind bars, they would assume control of the gang. But Zelig had friends in high places in Tammany Hall and was soon set free. Thus commerced a war between Zelig, and Tricker and Sirocco.

On December 6th, 1911, Zelig threw a shindig for his gang at Stuyvesant Hall. Tricker and Sirocco were not invited, but they sent their associate Jules Morello to the party, with the expressed intention of killing Zelig. But Morello had a few too many drinks at the bar, and started yelling, “Where’s that Yid? I’m gonna kill that Yid.” Meaning Zelig. Zelig heard the commotion, and before Morello could do him any damage, Zelig shot Morello four times, leaving him dead.

Zelig was on the pad of a corrupt Police Lieutenant Charles Becker, who wanted Zelig to kill Herman “Beansy” Rosenthal, a bookie who had made a formal complaint against Becker with the District Attorney Charles S. Whitman, for shaking down his gambling establishments. On October 12, 1912, Rosenthal was murdered in front of the Metropole Hotel near Times Square. But DA Whitman knew Becker was behind the killing and had him arrested for murder. Becker realized Zelig knew enough to put him behind bars for a long time, if not right into the electric chair. So not wanting to take a chance that Zelig would squeal, Becker hired “Boston Red” Phil Davidson to take care of Zelig.

On October 15, 1912, Zelig was drinking at Segal’s Cafe at 76 Second Avenue, when he got a phony phone call saying he was needed at 14th Street to settle a dispute. Zelig hopped on the Second Avenue Street Car. When the car reached 13th Street, Davidson snuck up behind Zelig and shot him once behind the ear, killing him.

“The Most Feared Man in New York City” was now dead at the early age of 24. Which didn’t help Becker much, since he was electrocuted in Sing Sing Prison in 1915 for the murder of Rosenthal.


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