Ben and Meyer soon learned as much about fashion from Rothstein as they did about organized crime. “Stylish dress emerged as the foremost symbol of Jewish transformation in the American city,” notes historian Andrew R. Heinze in one Bugsy biography. Rothstein was the style setter. “He taught me how to not wear loud things, how to have good taste,” Lucky Luciano later said. “If Arnold had lived longer, he could have made me pretty elegant; he was the best etiquette teacher a guy could have—real smooth.” A smart wardrobe spelled business success, and no one grasped the connection better than Rothstein. “He understood business instinctively,” Lansky recalled of Rothstein, “and I’m sure if he had been a legitimate financier he would have been just as rich as he became with his gambling and the other rackets he ran.”31 Siegel, at fourteen one of the youngest of Rothstein’s recruits, saw the older man as the father he wished he’d had: brash, debonair, a man of the world, with all the money he wanted.
Unlike most Jewish gangsters, Rothstein had grown up on the Upper West Side. His own father was a wealthy businessman, chairman of the board of New York’s Beth Israel Hospital, a senior member of his Orthodox Jewish community. Arnold could have been a great success in his father’s world. But he loved gambling and the excitement it brought him. Rothstein hobnobbed with New York mayor Jimmy Walker and the rest of New York’s elite. He was more than a gambler: he was a fixer, a financier, helping politicians and police chiefs, union bosses and Broadway producers. He was said to have fixed the 1919 World Series, but that may have been a useful legend. The bootlegging was for real.
A test run from England was a dark nocturnal drama crowned by great success: a booze-laden ship anchoring off Montauk, Long Island, motorboats shuttling on a moonless night from ship to shore, trucks carrying the liquor to warehouses in Queens. Soon Siegel and Lansky began renting trucks for bootleggers. The garage they used may have facilitated another new business. “Auto theft was their entrée to the big time,” says mafia historian Thomas Reppetto. “Siegel stole them, and Lansky fixed them up for resale.”32 The market for English liquor in America was constant and bottomless, and brought with it other profitable vices: gambling, for one; prostitution, for another.
Along with Siegel and Lansky, “The Brain” hired Salvatore Luciana and his fellow Italians Frank Costello, Vito Genovese, Albert Anastasia, and Giuseppe “Joe Adonis” Doto. Grudgingly, the Italians worked hand in hand with the Jews, among them “Waxey” Gordon, “Dutch Schultz” (born Arthur Flegenheimer), Abner “Longy” Zwillman, Louis “Lepke” Buchalter, and Jacob “Gurrah” Shapiro. All except Rothstein had come up from the streets of the Lower East Side or the old country. All were on their way to national notoriety. Their credo was simple. “No one gives it to you,” Costello reportedly said. “You have to take it.”33
A year later, after eleven successful voyages, Rothstein was out. A ship’s captain had snitched, and to Rothstein, the consummate gambler, the odds no longer looked good. His junior partners, including Siegel and Lansky, rushed to fill the gap. The Jews among them viewed Prohibition as rather silly: aside from sipping sacramental wine on holy days, most Jews, even criminals, had little taste for alcohol. But they saw the fortunes waiting to be made, and as fellow Jews, they trusted one another, up to a point. “To me, the whole thing was a matter of organizin’ a business,” Lucky Luciano later declared.34
Lansky and Siegel handled all aspects of the business, from setting up illicit stills in Canada and bringing in booze by boat across the Great Lakes to offshore runs along the Atlantic coast. They even ran a couple of Lower East Side speakeasies, one on Broome Street and one on Lewis, as one gangster, John Barrett, later recalled.35 What they didn’t do was claim a particular turf, as the tall and dapper Longy Zwillman did in parts of New Jersey, and Dutch Schultz did with the Bronx. They were freelance bootleggers, importing high-quality liquor from Canadian distillers like Samuel Bronfman and selling wherever they could.36 They were also enforcers, hiring out as guards for other bootleggers’ truck runs. That was when they became known, and feared, as the Bugs and Meyer mob.
Booze-filled trucks were subject to ambush, and no one was better than Ben Siegel at retaliating. One night, as one of Frank Costello’s drivers later related, Siegel, working for Costello on that run, saw a tree trunk across a country road, ahead of the truck he was guarding. Siegel told the driver to jam on the brakes, and raced into the forest to circle around the attackers he felt sure were there. Sweeping the woods with tommy-gun fire, he drew fire in return, from three directions. He fired a flare gun that illuminated the scene, along with an attacker running right at him. Siegel killed the man with a burst of fire, then kept shooting. When a backup team of Costello’s men arrived at the scene, they found a teenager “standing guard over four frightened men and a full truck of liquor, untouched.”37
At some point, such crazy courage earned Siegel his nickname. It was a name he hated and bridled at whenever he heard it. Soon, in the world of organized crime, it became known that a good way to get killed was to greet Ben Siegel as “Bugsy.”
The name, of course, had a darker connotation: that Siegel really was crazy as a bedbug, so quick to flare, so willing to kill. The FBI, in one of its later memos about Siegel during its surveillance of him, casually called him “insane along certain lines.”38 Journalists after his death called him a sociopath, someone capable of violent acts without conscience. Certainly he could kill without any apparent remorse. But no one ever heard of Siegel taking to a psychiatrist’s couch, and the symptoms, from murderousness to megalomania, were just that: symptoms, and secondhand ones at that.
Some aspects of Siegel’s character seemed incongruous with “sociopath” or “psychopath,” even used loosely. Siegel had many close friendships that he maintained for life. He adored his daughters and felt, until the end, a certain loyalty to his wife, at least as the mother of his children. Loyalty was his most admirable trait. He remained loyal to Lansky, Luciano, and the rest of the Syndicate’s higher-ups, until Siegel’s last few nerve-wracking months, when he may have skimmed from the till and stolen from his partners, as he struggled to keep the Flamingo afloat. At that point, with the very real prospect that his partners might kill him, he grew more physically abusive and may, in some sense, have lost his mind. But that was all later.
By chance, a psychologist did offer a seat-of-the-pants analysis of another gangster, Frank Costello, which had some bearing on Siegel. The shrink, who came to know Costello through the gangster’s lawyer, ventured a few conclusions. “An enormously fascinating man,” he declared. “Egocentric, but with insecurities in several directions. He is absolutely sure of his own ability, and his own intelligence. And he has a thirst for power that’s extraordinary. But let’s look at his background. . . . He saw his father reduced to working with a pickax for slave wages.” Siegel’s father had endured equally grueling and degrading work. Both gangsters had grown up in New York slums—East Harlem in Costello’s case—and moved, as soon as they could, to fancy neighborhoods of high social status. Neither man would ever forget the horrors of his childhood. The shrink who befriended Costello felt the gangster would do anything—anything—to keep from slipping back into poverty. So, it was fair to say, would Ben Siegel.39
By the mid-1920s, bootlegging had made Siegel a rich man who indulged in daily trips to the track. A very young rich man of barely twenty-one. For these outings, he wore checked sport jackets of houndstooth plaid, high-waisted pants with pegged cuffs, and custom-made alligator shoes. At night, he went out garbed in well-cut suits, with the colorful ties and monogrammed shirts of a dandy, fending off the winter chill with a hard-shelled derby hat and a velvet collared, full-length cashmere coat.40 He was a long way from his days as an urchin on the Lower East Side.
And yet, as Meyer Lansky observed, Siegel didn’t cling to money, fearful that his next haul might be his last. He spent extravagantly, as if money didn’t matter at all. Getting it was a game, spending it just an excuse to play the gam
e again. Perhaps he took some satisfaction in flaunting his newfound wealth to his father, who was still working as an operator in a pants factory.41 To make money, you had to be ready to lose it. Max Siegel would never understand that simple truth. He let his fear keep him chained to that pants machine, making his pittance with no chance of earning more, the minutes of his life ticking away one by one, trapped by a world he’d thought would make him free. Real freedom meant knowing you could always earn more, as much as you liked, if only you knew how to do it.
On his evening rounds, Siegel loved making an entrance at one of the city’s top speakeasies: the West Side’s Club Durant, the 21 Club on West 52nd Street, and Chumley’s in the Village, where the literary crowd gathered. More for business than anything else, Siegel and Lansky also hung out at the Back of Ratner’s, a garage-cum-speakeasy behind Ratner’s delicatessen by the Williamsburg Bridge. There the gangsters would rent cars and trucks to other bootleggers. Florabel Muir, a society columnist who worked both coasts, often ran into Siegel on her rounds. She invariably found him “arrayed in the habiliments of an easy money guy,” and was struck by his cold blue eyes.42 Two decades later, Muir would be the first journalist to reach Ben Siegel’s murder scene and would note, being the dispassionate reporter she was, that one of those cold blue eyes had been propelled by a bullet into the living room’s far wall.
Before Prohibition, no Jewish gangster would have been welcomed by the company in those nightspots. Lawyers, financiers, judges, and debutantes—all would have barred the interlopers from their nightclubs. Now they had no choice but to check their antisemitism at the door and socialize with them. The Jews, after all, had the money, the muscle, and the booze.
Bootleggers were glamorous, with the alluring hint of a dark side. Not by chance did F. Scott Fitzgerald make Jay Gatsby a bootlegger. Nor, by chance, did he have Gatsby meet up at a speakeasy with Meyer Wolfsheim, himself a bootlegger. Wolfsheim was based on Arnold “The Brain” Rothstein, to judge by Gatsby’s aside to Nick Carraway that Wolfsheim fixed the 1919 World Series. But he could just as easily have been Ben Siegel.
Siegel enjoyed the women he met on his rounds, and went from one to the next, often with introductions made by his good friend Mark Hellinger, the Broadway newspaper columnist who affected tinted glasses, black suits, black shirts, and white ties. Hellinger was on his way to fame as a theatrical and Hollywood producer. He prided himself on using true-to-life crime stories provided by Lucky Luciano, Dutch Schultz, and Bugsy Siegel, and they loved recounting them over drinks at Sardi’s. “Broadway was the gangsters’ ideal cultural milieu,” notes Albert Fried. “Its very existence served as their vindication.”43
Still in his early twenties, Siegel now had the patina of class, and prided himself on it. “Class, that’s the only thing that counts in life,” he said. “Class. Without class and style a man’s a bum, he might as well be dead.”44 Along with class, he had the brute force, so it was said, to claim a dollar a case of liquor—a dollar for every case of liquor—that came in to the New York docks. That was a lot of power, and a lot of cash. But he was about to reach for more.
2
Marriage and Murder
BEN’S FIRST BRUSH with the law came in January 1926, when a woman filed rape charges against him in Brooklyn. Doc Stacher, Meyer Lansky’s right-hand man, explained years later what seemed, for Siegel, a most untypical crime.1
Siegel was barely twenty when he ran into a woman at a bar who reminded him, bitterly, that they had met before. Back when Siegel was fourteen, she had accused him of making an Irish youth disappear. Siegel had then pushed his way into her apartment and roughed her up. Apparently he had tried to rape her, only to fumble in the clutch. On seeing him again, the woman mocked his manhood. A furious Siegel followed her out of the bar and raped her in a nearby hallway. Or so said Doc Stacher. The woman, doubtless under pressure, soon withdrew the charges. No further charges of rape or any such crime ever darkened his docket.
Siegel’s next charge seemed more in keeping for a now-notorious enforcer. He was arrested for carrying a concealed weapon in Philadelphia.2 The mug shot taken on that date—April 12, 1928—offers the first known image of Ben Siegel, a snap-brim hat pulled low on his forehead over an icy, baleful stare. The police photographer must have decided the hat had to go: his profile shot has Siegel bareheaded, with a handsome profile, aquiline nose and strong chin. He seems more relaxed in profile, even bemused. Together, the front and profile shots seem to reveal two sides of the man: the murderous and the urbane. Siegel chose to skip his $1,000 bail and become a wanted man in Philadelphia, a harmless enough risk since New York showed no interest in extraditing him.
Early that November 1928, Arnold Rothstein was found shot and near death in his suite at the Park Central Hotel. Gambling had made his fortune but sealed his fate: always a gambler himself, he had become an addict, making ever wilder bets and appearing distracted, even mentally ill. Possibly he had gone into international drug trafficking and become a major dealer, but if so, this was a startling sideline for his Jewish colleagues, who so far had generally avoided drugs. Almost certainly, Rothstein owed his death to an unpaid debt, though he refused to say who had shot him, and why.3 There was a lesson in that for Ben Siegel, not to let his own gambles get the better of him, but it was one he would fail to heed again and again, to Meyer Lansky’s chagrin.
By the late twenties, Siegel and Lansky were said to be bringing more booze into the United States than any other bootleggers in the land.4 Rumors, never substantiated, had them overseeing their share of narcotics trafficking, too.5 There was, of course, no Dun & Bradstreet to gauge their business success.
For both men, marriage seemed an appropriate next step. In 1927, Siegel and Lansky began double-dating two Lower East Side girls. Ben went with Esther Krakauer, also known as Esta and Estelle, whose family were onetime neighbors of the Siegels on Cannon Street. Her father, like Ben’s, was a tailor. “Not a looker,” recalls Wendy Rosen, one of Esta’s granddaughters—and Ben’s. “A very tall, lanky woman with Lucille Ball red hair.” Also, says Wendy, “a very unusual nose, prominent, with a flat bridge, like an eagle’s nose. And very tall and bony.” Esther did have beautiful blue eyes, Rosen says. More important, she was crazy about her dashing beau. According to her granddaughter, she always would be.6
Meyer chose Anna Citron, also dark-haired, also a longtime family friend, but from a considerably higher social station than either the Lanskys or Siegels.7 Anna’s father had started as a produce wholesaler and risen to command his own chain of fruit markets. He wore pinstriped suits and lived on a New Jersey estate near Longy Zwillman in South Orange, an appropriate town for a produce king.8
The girls didn’t mind that their boyfriends were bootleggers, though when asked, they were careful to say that Siegel and Lansky ran an auto garage. They liked swanning as a foursome into a speakeasy and drawing all eyes. But both were proper young women, ready to start families. According to Wendy Rosen, neither knew how deadly their fiancés were.9
Siegel married first. The ceremony was held on January 27, 1929, at 332 Rogers Avenue, a brownstone in then-bourgeois Crown Heights, Brooklyn. Ben listed his occupation as “salesman” and his address as 546 Gates Avenue in Brooklyn’s Bedford-Stuyvesant, also a good neighborhood at the time. Esther, at seventeen, was underage, and so a consent certificate was needed. It was signed by Esther’s father; her mother was noted as deceased. The most striking fact in the marriage certificate was that a rabbi officiated. His name, in flowing script, is illegible on the form; the address on Rogers Avenue may have been his own.
Meyer Lansky married Anna Citron less than four months later, on May 9. Again, a rabbi officiated: Rabbi Isaac Leib Epstein. Lansky listed his residential address as 6 Columbia Street on the Lower East Side, and his business as “auto rental,” rather amusing if he was, indeed, still selling stolen cars. Anna’s father’s name was Moses, her mother was Selma; both parents were Jewish and had been born in Russia.
The two grooms served as each other’s best men.10
The presence of rabbis at both services was telling. Lansky and Siegel might have no ties with local synagogues. Yet they had chosen to enter Jewish marriages and identify themselves as Jews. If they had given any thought to marrying without a rabbi, they had acted otherwise, doing what they most strongly felt: to honor the faith of their fathers and, unlikely as it might seem, to recognize that the same bonds that held them together as gangsters held them together as Jews. These included the presence, if not the practice, of religion; Yiddish as the communal language if no longer the dominant one; and the resonance of Jewish values, shunted aside if business required, but always there in the fabric of their lives. Most emphatically, they embraced the shared destiny of the Jewish people, unfurling here in America with opportunity, one future day, for all.
The ever-practical Lansky arranged for his honeymoon to take place during an Atlantic City conclave of top-tier gangsters in mid-May, 1929, a meeting he himself planned and headed up. Dozens of attendees gathered, from Lucky Luciano and Frank “The Prime Minister” Costello to Vito Genovese, Joe Adonis, Longy Zwillman, and, to be sure, Ben Siegel. During the meetings, Lansky’s and Siegel’s brides lounged by the pool with other gangsters’ wives and girlfriends. When business was done, the gangsters joined them or took pensive strolls along the beach, their shoes and socks in hand, their trousers rolled up. The gathering was a first formal attempt to plan for the inevitable end of Prohibition. How would the gangsters sustain the cash flow that bootlegging had brought? Ending the bloodshed among rival gangsters was the other urgent order of business, following the Valentine’s Day massacre of the preceding February in Chicago, where Al Capone had orchestrated the murder of seven rival gangsters. Capone was at the conference, too, his temper even less in check than Siegel’s.11 Atlantic City was where the notion of a national Syndicate was first aired, with strict rules for all, but more blood would have to be shed before the gangsters agreed on who should lead them, and how the pie of vice should be divided, vice by vice and market by market.
Bugsy Siegel Page 3