Michael Shnayerson—

By the age of twelve, Siegel was essentially spending his days as he pleased—but what he pleased to do, more than play games, was embark on petty crime.

Ben learned to hit up pushcart peddlers for protection; those who declined to pay a weekly fee might find their pushcarts torched. He learned that the drivers of horse-drawn carriages could be threatened as well: without protection, their horses might be poisoned. Arson and poisoning were crimes of choice for street urchins: “property crimes” easy to do without guns.

For a boy Ben’s age, the gangs were irresistible. “It was the exceptional, almost abnormal boy who did not join the gang,” recalled one veteran gang member. “The gang was romance, adventure, [and] had the zest of banditry, the thrill of camp life, and the lure of hero worship.” Lincoln Steffens, the famous muckraker, saw those children up close. “We would pass a synagogue where a score or more of boys were sitting hatless in their old clothes, smoking cigarettes on the steps outside, and their fathers, all dressed in black, with their high hats, uncut beards and temple curls, were going into the synagogue, tearing their hair and rending their garments. . . .Their sons were rebels against the law of Moses; they were lost souls, lost to God, the family, and to Israel of old.”

What separated Siegel from his fellow urchins was an utter absence of fear. He loved the adrenaline rush of breaking rules and taking risks. Siegel became known as a chaye—a beast. He scared even his mother. “I never sent Maurice to talk sense into Benjamin,” Jennie was quoted as saying years later, “because I was afraid for my younger son, my baby. Benjamin’s temper, I knew. He would have probably beaten him up. So I sent the girls after him. But it did no good. Benjamin wouldn’t listen. He told the girls that he was a man and that he wanted to lead his own life.” Some years later, Ben would pay for Maurice to go to college and medical school, but that would remain a family secret, to Ben’s enduring hurt. Maurice, as a niece observed, felt shame for taking the money, and may not have forgotten the pummeling he took from his older brother when both were young.

In the early years of the twentieth century, a whole generation of immigrant boys took to the streets. “Unsupervised, the boys of the Lower East Side spent much of their time in front of the pool rooms and salons which dotted the neighborhood,” notes Lower East Side historian Jenna Joselit, “hoping to be called upon to perform an errand for one of the regulars.” Underworld characters became their role models, taking the place of sad-sack fathers. “The underworld characters were so fascinating because on top of everything else they exemplified the cynical truth behind the American dream,” notes Albert Fried in The Rise and Fall of the Jewish Gangster in America. It was “the incontrovertible fact that vice and crime were escape routes to freedom and that all the preaching at home and in school and in the press were so many lies and deceptions. Success taught its own lessons.”

Later, Siegel recounted his first actual crime, robbing a loan company. “I had to run like hell for about ten blocks, carrying two bags full of small change, before the guy chasing us ran out of breath and quit. It might have been better if they’d caught me because after that I was game for anything.” Already, the lineaments of a violent character were emerging. Ben was gleefully daring, impulsive, always ready for a fight. At the same time, he was willing to learn.

From Bugsy Siegal by Michael Shnayerson. Published by Yale University Press in 2021. Reproduced with permission.

Michael Shnayerson became a contributing editor at Vanity Fair in 1986 and is the author of eight books on a range of nonfiction subjects, including Boom: Mad Money, Mega Dealers, and the Rise of Contemporary Art.

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