ON PAPER, HARRY DONENFELD WAS a printer. He and his three brothers ran the Martin Printing Company in Lower Manhattan in the shadow of the Brooklyn Bridge. The nine-floor building was filled with printers, whose heavy machinery, mixed with the trolleys crossing the bridge, made the whole place rattle and shake.
It wasn’t the prettiest spot in town, but was a vast improvement over where the four brothers grew up. Harry had worked his way out of poverty on the Lower East Side, having come at the turn of the century at age eight with his family from Jassy, the cultural capital of Romania, just as the government there decided to bar Jewish students from its public schools and colleges. The Donenfeld kids all slept in one bed together in a vermin-infested cold-water flat on Stanton Street. Each of the brothers now lived in the Bronx in neat, respectable houses. But the trip from the Lower East Side had been a long one. Harry had been a newsboy, a teenage gang member, and a garment worker. Now as a printer, he felt he had finally arrived. He was making good money. But there was so much more for the taking in New York City.
Bootlegging was in full swing in America. And Harry Donenfeld was about to get a taste. Harry was short—only five foot two—with a reedy voice and a thick New York City accent. But he was the boldest of his brothers, the middle of five children. He was also incredibly dapper and charming, with a high forehead, a slight slope to his nose, and a flinty spark in his dark eyes that meant he could cause trouble when he wanted.
On the Lower East Side, Harry had been in all the local gangs. There were the Allen Street Cadets, the Henry Street gang, the McDonald Street gang, the Five Pointers, and the Boys of the Avenue, the local Jewish gang filled with Yiddish-speaking shtarkers (tough guys) like Harry. Some gang members learned to pick pockets, gambling with that “found” money on horses, cards, and fights; running numbers; and rumbling with the rival gangs. The numbers Harry ran were called the policy racket, involving penny bets and steep odds at 999 to 1. Policy took its name from the insurance industry. The payoff was usually 600 to 1.
Some of Harry’s childhood troublemaker friends were now grown-up gangsters. To make extra money, real money, Harry started running Canadian whiskey and Molson ale down to New York for his old buddies. The illegal liquor was stored amid Harry’s giant paper rolls in his trucks and at the printing company.
Bribing the cops so they wouldn’t look too hard in the weighed-down paper trucks, Harry’s Mob friends would pick up the booze, Gillette it (slang for cut it), and deliver it throughout the city. Drivers would drop their crates at stores with painted windows, basement brownstone apartments, and the back rooms of restaurants—the speakeasies of New York. Harry was a regular customer at many of those “speaks.” When Prohibition began in 1920, the city was home to fifteen thousand saloons, clubs, and bars. By the mid-twenties, the number had more than doubled.
The Broadway Mob, Harry’s connection, supplied booze to many of the high-end speakeasies, like the Stork Club and the 21 Club, as well as the Cloud Club high atop the Chrysler Building. Harry developed a close bond with Francesco Castiglia, a fellow Broadway Mob bootlegger whose wife happened to be Jewish. Francesco, originally from Southern Italy, would change his name to Frank Costello. It was through Costello that Harry met the gangster’s Chicago associate, Moe Annenberg—publisher of the Daily Racing Form and other newspapers. He chose Harry to print six million promotional brochures as inserts for Hearst, the huge national newspaper chain, for whom Moe handled distribution. It was Harry’s first big score—aside from the booze.
The Donenfelds’ other printing clients included city hall, the International Ladies’ Garment Workers’ Union (“Look for the union label!”), and proto-feminist Margaret Sanger, who had them run off her illegal family-planning pamphlets and her newsletter—the Birth Control Review—promoting contraception. Under the Comstock Act passed by Congress in 1873, it was still against the law to distribute, sell, or possess contraceptives or any information discussing them, but Sanger, the founder of what would later become Planned Parenthood, preached that reproductive freedom was the key to women’s equality. Sexual pleasure without procreation was not immoral, she argued. And Harry wholeheartedly agreed.
Most printers regarded Sanger’s pamphlets “a Sing Sing job”—printing them would send you straight to prison. But Harry was happy to oblige. Anything for a buck, and to shake things up. He would not only print Sanger’s material but would store her boxes of illegal diaphragms behind his big rolls of paper, right next to the booze.
Not surprisingly, Harry developed a strong taste for liquor—an occupational hazard—and would barely make it back to his home in the Bronx every night after tying one on. He loved to knock back a good highball (or two or three), but his favorite drink was a Heineken. His wife, Gussie, hardly ever saw him anymore. And she missed him.
The two had met at the Seward Park public library branch and worked together at the Great Eastern Waist Company on Twenty-Seventh Street, selling tailored women’s blouses to wholesalers. Harry—with his thin mustache and black, slicked-back hair—cut quite a figure in his suit and vest and his fresh white starched shirt and collar. When young Harry met teenage Gussie, three years his junior, he took her around to all his favorite restaurants and cafés in the city. But what Gussie loved best about Harry was how he made her laugh. Harry was a practical joker and once gave a hotfoot to the up-and-coming heavyweight boxer Jack Dempsey, lighting his laces on fire. Dempsey, known for his powerful punches, turned around and playfully jabbed Harry, accidentally breaking his arm. But the two would stay good friends.
Harry and Gussie had been best friends back then, not just working together but protesting the Great War and the draft, attending Socialist rallies on Second Avenue, near their thirty-dollar-a-month newlywed apartment in the East Village. The cafés and bohemian bars were filled with young writers, artists, anarchists, and proponents of free love drawn to the area for its low rents. He and Gussie worked as Socialist poll watchers together during the 1918 elections and had attended what the radicals called Second Avenue University. At the intersection outside their railroad apartment, Socialist candidates set up small wooden platforms, giving speeches and lectures late into the night. All sorts of people attended those revival meetings—men, women, immigrants, Americans, Black, white—listening to talks not just on politics, but philosophy, history, and economics, the traffic stopping to avoid the huge crowds.
Though Harry and Gussie didn’t go to college, they got an education on that street corner. They had become adults together there, holding hands under the stars and feeling they could change the world. Instead, Harry had changed. Ever since they had moved up to the Bronx, it was as if a light switch had been flipped. Gussie wasn’t sure if it was the heavy drinking or the reality of starting his own family staring him in the face. Or maybe Harry had always been a bastard and she just hadn’t noticed.
In 1925, Harry began running around Brooklyn with a married woman from Manhattan Beach. For people who had grown up in working-class and poor neighborhoods like Harry and Gussie, free love had a different name: cheating. Gussie filed for divorce and got a boyfriend of her own. But it was just so Harry could get a taste of his own medicine. Harry, it turned out, was immune.
There was the nurse he had the long affair with, and the woman he was dating whom he fought with at a bar and grill on the corner of West Twentieth and Seventh Avenue. The woman had grabbed a carving knife and stabbed Harry. But Harry’s immunity stuck: He survived. And Gussie stayed.
Harry’s shenanigans—the cheating, the drinking, the hanging with mobsters—did not sit well with his brothers, who were growing to dislike Harry as much as Gussie did. There was the time, years later, that a printing client, a mobster with a very bad stutter, came in to do business. Harry, always the joker, told him to wait a moment. He then ran and grabbed his youngest brother, Irving, who also had a stutter, and told him to wait on the guy. Moments later, the client stormed off—sure he was being made fun of—and Irving appeared, his face pale. “W-w-w-what are you t-t-t-trying to do?” Irving said. “He’s going to k-k-k-kill me.” Harry thought it was hilarious. His brother did not.
Harry broke with his two older brothers and started his own company on West Twenty-Second Street, printing Screenland, a successful Hollywood fan magazine. Irving decided to join him in the new business venture. Harry told Gussie it was a fresh start for them both and she foolishly believed him. She hoped the man she had fallen in love with under the stars on Second Avenue was still inside there somewhere, hidden beneath the fancy suits and the pinkie ring. Before she knew it, Gussie was pregnant. The following year, Harry shamelessly formed Irwin Publishing—named for his newborn son—printing a series of sex pulp magazines called Snappy Stories, Spicy Stories, and Pep!, which was filled with topless girls and gags.
Nothing was sacred to Harry, not even his firstborn son’s name, as long as there was a buck to be made. And besides, he would argue, if it wasn’t for sex, little Irwin wouldn’t even exist, now would he? Fatherhood, however, did not cure Harry’s wandering eye. He slept with the pulps’ female editor, Merle Williams Hersey, adding her to his long list of mistresses. And editors.
The girlie magazines were called smooshes and were incredibly profitable. Their stories—accompanied by erotic photos and illustrations inside, and even brazenly on the cover—were said to revolve around one plot:
Boy meets girl.
Girl gets boy into pickle.
Boy gets pickle into girl.
They involved deep kisses and heavy petting of “alabaster orbs” and “snowy white globes,” with lots of trembling and throbbing and quivering. The writers always cut away before any serious action, hardly living up to the promise of the topless cover girls luring readers in. But no one came for the prose. It was all about the occasional “art” photos and line drawings: topless women shaking cocktail shakers over their heads, topless women kissing pilots in cockpits, topless women cavorting with the devil, topless chorus girls, housewives, farmers’ daughters climbing into haystacks or into bed.
When the stock market crashed in 1929, Harry’s sex pulps not only didn’t feel the shock but increased profits, selling cheap thrills to the masses for twenty-five cents at newsstands. Business was so good that Harry hired a new accountant, Jack Liebowitz, whose stepfather, Julius, had been a union steward for the International Ladies’ Garment Workers’ Union (ILGWU). Harry and Julius had played cards together.
Jack, a full head taller than Harry at five foot eight—but with much less personality—had come from Ukraine with his family when he was ten years old, settling on the Lower East Side. Back in Ukraine, he had watched his older brother die from diphtheria after drinking tainted water from a barrel outside their house. A few years younger than Harry, Jack had also worked as a newsboy and remembered watching from the roof of his tenement apartment as smoke billowed from the Triangle Shirtwaist Factory fire. He had a head for numbers and very good handwriting, so good that when he was a boy his teachers would have him help write out the report cards for the whole class. Crafty even at a young age, Jack stole a few and, one year, wrote out a fake report card for himself so he could skip a grade.
His refuge was the newly built Seward Park public library, the place where Harry had first encountered Gussie. It had a beautiful roof garden, where Jack and the other smart neighborhood kids would gather at wooden tables and do their homework or simply read for pleasure. Jack would borrow books—fairy tales, Westerns, and the novels of James Fenimore Cooper—and devour them at home each night near the cast-iron stove in the kitchen, banging a big stick every now and then to keep the rats away. As in Harry’s tenement apartment, there was never enough food to eat and he never had a coat, just a sweater in winter. Jack and his three brothers shared a small cot, which was incentive enough to study, cheat, or do anything he needed to do to get out into the world on his own. To say he and Harry were self-made men was a gross understatement. They were survivors.
After dabbling in Socialism and studying at New York University, Jack got his accounting degree and landed a job with the ILGWU, managing the union’s strike fund, the money set aside for when and if its members walked off a job. Jack invested that money in the stock market, but after the Wall Street crash, the funds took a dive, and so did Jack. With very few clients, Jack wound up working for Harry.
With Jack at the helm, Harry expanded his distribution business. Jack explained that distribution was where the real profit was. For news vendors, the contact for the magazine was the distributor, who would visit the newsstands and take orders for the publisher. The distributor would then deliver the magazines and push for good placement, then collect on sales made. Depending on the distributor’s deal, they would take a certain cut of the profit, maybe slightly less than half. But newsstands paid the distributors directly for what was sold, so until all the unsold copies were returned and the distributor showed his hand, there was no way for the magazine to know how much money they were owed.
The covers of the returns were ripped off or a hole was punched in them. Those damaged copies would then be sent by the publisher overseas or to magazine dumps, who would sell them at a discount. In the gap time, a distributor could invest the money, lend it out, or simply hold on to it. Sometimes if you held on to it long enough, the magazine would go out of business, and then Harry and Jack could step in and take it over.
The yin to Harry’s yang, Jack Liebowitz was the tight-assed, detail-oriented numbers man to Harry’s rambling, backslapping, hotfoot-giving guy. Though he looked like a comic villain with his skinny mustache, Jack played by the rules that Harry often trampled: he avoided doing anything outright illegal, but morals and ethics were definitely off the table. The little boy with the doctored report card was still alive and well in Jack’s soul. If Jack even had a soul. He would one day become known as the Eraser by all the people he screwed over and made disappear—not through Mob hits, but through contracts and court cases. Jack was, like Harry, a goniff—Yiddish for a dishonest son of a bitch. Their coming together was like earth meeting sky, like Bergdorf meeting Goodman, Astaire meeting Rogers. Or Sundance meeting Butch. History—business, entertainment, and criminal—was about to be made.