Bugsy Siegel

by Michael Shnayerson

  The Racing Form and other racetrack sheets lay spread on the table. When Captain William Deal of the vice squad asked about them, Raft declared that he and his friends were doing exactly what they seemed to be doing: placing bets on horses. Captain Deal apparently disagreed: the men were bookmaking, he declared, acting as bookies rather than betting on their own. With that, Deal took the phone from Siegel’s hand and ripped its wires from the wall.

  Siegel and Smiley were charged not only with bookmaking but with conspiracy, a felony that could bring significant jail time. Raft, on the other hand, was told he could leave. Furious, the actor insisted on being charged with his friends. At a preliminary hearing, Raft took the stand and heaped scorn on Captain Deal. The prosecutor finally agreed to drop the felony charges if Siegel and Allen Smiley pleaded guilty to the bookmaking count. After paying a $250 fine, the two men were freed.24

  Raft actually benefited from the affair. His courtroom appearance with Siegel buffed his image as a real-life gangster, winning him more gangster roles. Smiley came out ahead, too. Recently he had opened a nightclub with Siegel’s backing, and the press was good for business. Only Siegel lost out, his California record clean no more.

  Irate, Siegel decided in earnest to sell the Delfern Drive house and move his base to Vegas, despite the desert heat. The cops and politicians in Vegas were more sympathetic, he felt, the new hotel-casinos enticing. And who was to stop him from building a casino of his own, one bigger and more dazzling than anything else on the Strip? Surely the Syndicate would back him on that.

  There was another reason, just as compelling, for Siegel to sell his house and start a new life. His romance with Wendy Barrie behind him, he had met a woman so sensual and exciting that he could actually imagine divorcing Esther and marrying her. At some point in this period, he must have told Esther about Virginia Hill, because Esther moved to Manhattan with the girls, who enrolled in the Calhoun School on the Upper West Side. She had tolerated Siegel’s Hollywood flings, his long cross-country absences, and more painful, his public relationship with Countess Dorothy di Frasso. Esther wasn’t quite ready to ask for a divorce: the very idea appalled her, given her conservative upbringing and the love she still felt for Siegel. But nor did she appear willing to remain under the same roof as her husband. To judge by the way Siegel began making the rounds with Hill on his arm, the marriage was kaput.

  Itching to acquire a hotel-casino of his own, Siegel approached Tom Hull, the owner of El Rancho Vegas, whose flat tire four years before had led him to build the Strip’s first one. Siegel made an offer for El Rancho; Hull declined. Siegel raised his offer; Hull declined again. “You may say for me,” Hull told the Las Vegas Review-Journal, “that the people of Las Vegas have been too good to me for me to repay them in that way. Mr. Siegel has contacted me several times with an offer to purchase, but I have told him I was not interested—and that goes for all time.”25

  Hull’s disdain only hardened Siegel’s ambition to rule, or at least dominate, Las Vegas. So eager was he to start a new life that he put the Delfern house on the market for $85,000. A quick bite of interest came from actress Loretta Young and her husband, Tom Lewis, who wrote a check for the $8,500 down payment. Soon after, they made a more detailed examination of the place and found termites. Young and her husband asked only that Siegel pay $350 to exterminate the bugs. “Like hell I will,” he declared. At that, they withdrew their offer, losing their down payment but extricating themselves from a house full of bugs. Siegel retaliated by taking them to court. A first judge sided with Young and her husband; a higher judge did, too. In the end, Siegel spent two years tangled in the proceedings, only to sell the house at a bargain price of $75,000.26

  Possibly unaware of the Delfern house history, and that of its owner, a young Los Angeles woman let her curiosity lead her to the front door. She was a wartime European refugee whose son, a financier named Peter Gregory, tells the story to this day.27 The woman was his mother. Curiosity led the woman to 250 Delfern, where she found herself face to face with a darkly handsome, impeccably dressed man who introduced himself as Ben, and invited her in.

  The handsome owner gave Gregory’s mother a tour of the place; pleasantries were exchanged. The owner then motioned her to a seat in the living room.

  “I like the house very much,” Gregory’s mother said. “But I have to admit the price is high for me. What’s the best price you could give me?”

  Siegel put a hand up as if to wave off the thought. “I never do business with ladies,” he said. “I’ll take whatever price you offer.”

  Mrs. Gregory was enjoying her visit, and the intensity of the handsome owner’s gaze. There was, perhaps, a trace of flirtation between them. Mrs. Gregory was a very handsome woman in her early forties, not unaware of her looks. She giggled. “Oh come on,” she said. “How little would you take?”

  “Whatever you want to pay is fine,” Siegel said.

  “Well, all right,” said Mrs. Gregory. “Would you take a dollar?”

  The man smiled. “Yes, of course. If you want to buy this house, I will sell it to you for a dollar.”

  Mrs. Gregory grinned. “You can’t be serious,” she said.

  The owner leaned toward her. “That’s where you’re wrong,” he said. “You can buy it for a dollar.”

  At that point Mrs. Gregory thought it best to leave. She promised to bring up this offer with her husband that night, and she did.

  “You did what?” her husband said. “You offered to buy a house from Bugsy Siegel for a dollar? Do you know what he would do if we actually did that?” Neither Mr. nor Mrs. Gregory knew what would happen, since Mrs. Gregory never went back to the house. There was something so mesmerizing and intense about Siegel, though, that Mrs. Gregory never forgot the episode. She had a feeling she really could have bought the Delfern house for a dollar and not incurred any retaliation. It was just something she saw in those brilliant blue eyes.

  At some point soon after that curious encounter, Siegel moved out of the Delfern Drive house. He had done all he could, sparing no expense, to make it a perfect family home. But surely even he knew he was to blame for the failure of family life its empty rooms represented.

  In the summer of 1944, in response to a letter from the U.S. Draft Board, Siegel offered a few updates on his wartime status. He had changed his address from 250 Delfern Drive to 721 North Doheny Drive, a home in Beverly Hills owned by his sister Bessie and her husband, Sollie Soloway. His annual income, he reported, was $50,000. He called himself an investment broker, and explained, “I consider various propositions concerning investments in enterprises, and if satisfactory, enter into such deals.” As to the specific nature of those deals, “I do the following kind of work: I usually obtain an interest in return for my work. I’m required to make trips to appraise and investigate all matters connected with enterprises, and to negotiate terms.”28

  It was an apt description for an entrepreneur, but no less so for a freewheeling gangster about to embark on the business challenge of his life, one in which daily decisions, involving tens or even hundreds of thousands of dollars, would have to be made. Soon he would see how equipped he was to make them.

  7

  The Start of an Ill-Starred Romance

  NO RECORD EXISTS of Ben Siegel’s first meeting with Virginia Hill. History does provide the next best thing: George Raft’s first meeting with her, at about the time she and Ben Siegel fell into their torrid affair.

  Raft liked driving his black Cadillac convertible from his home in Coldwater Canyon down to Romanoff’s restaurant in Beverly Hills. There, as usual, he would be warmly greeted by “Prince” Romanoff and led to his favorite booth as all eyes followed. Decades had passed since he’d whirled lonely women around a dance floor for cash, but he still moved with a dancer’s ease and grace.

  This particular evening, Raft noticed a familiar figure in a nearby booth. Giuseppe Doto, better known as Joe Adonis, was a key member of the Syndicate, and one of Meyer Lansk
y’s closest friends. With him was a beautiful young woman Raft had never seen. Intrigued, he went over to pay his respects.1

  For a moment the two men talked of Ben Siegel and his efforts to sell the mansion on Delfern Drive. Then Joe Adonis remembered his manners. “George, I’d like you to meet a friend of mine, Virginia Hill. Virginia, this is George Raft, as if you didn’t know.”

  Hill had iridescent gray-green eyes, a dazzling smile, and a mane of dark red hair, falling around her bare, petite shoulders. Raft was mesmerized. “You from out of town?” he asked.

  “Chicago,” Hill murmured. “But I’ll be living here now.”

  “Maybe we’ll be seeing you around,” Raft said. He was right about that. Raft would be seeing a lot of Virginia Hill. And so would his friend Ben Siegel.

  Doto had had his amorous innings with Hill—he was, perhaps, having them still—and he would say he knew just how to deal with a girl like her. She loved sex, took pride in doing it well, and saw it as sport. You didn’t fall in love with a girl like that; you had fun. But somehow, Siegel was about to lose sight of that fact. He would let Virginia Hill become the love of his life, then let her take over his life. You couldn’t separate Hill from Ben Siegel’s murder, Doto would say, whoever fired the shots. Hill was charming and fun, a crazy spender, and in her way, a great beauty. But she would bring chaos into Ben Siegel’s life, and chaos, in the end, was what would kill him, whether the shooter was a Syndicate hire, or a race wire rival, or someone else altogether.

  It was a tragedy, really, “Joe Adonis” would say. A great tragedy for all concerned.

  Later, Siegel and Hill would speak of each other as soulmates, but they were more like alter egos. Like Siegel, Hill had grown up in abject poverty. Like Siegel, she had fought her way out at an early age, self-reliant and tough. The only difference was that Hill had a sponsor in the Chicago mob, a middle-aged mole of a man named Joe Epstein, who smoothed her path.

  Virginia Hill, nicknamed Onie, was one of ten children, her kid brother Chick later recounted. She was born on August 26, 1916, in the small, mostly black town of Lipscomb, Alabama. Lipscomb was dominated by the Woodward iron company, where most residents worked until they could work no more. Her father nursed a violent temper and had more interest in bartering than earning a livelihood. “He could leave home in the morning with nothing but a pocketknife,” Chick later said, “and come back at night with a horse.” Another account suggests “Mack” Hill’s trades were crooked, and that he did nothing to support the family, womanizing and drinking and beating the children.2

  Soon after Virginia’s birth, the family moved to nearby Bessemer, a larger industrial town where her mother, Margaret, ran a boardinghouse. From an early age, Virginia took charge of her siblings, warding off their drunken father and, according to one biography, slamming him on the head with a skillet when she was as young as seven. According to that account, Hill learned to regard all men as untrustworthy, and she never let down her guard.3

  Overwhelmed by work and her querulous brood, Margaret situated the children among relatives. Virginia ended up with a grandmother on a cotton patch and became a lifelong tomboy. Later, Hill told the Kefauver Commission on Organized Crime that she left school in the eighth grade. By one account, she eloped at fifteen with the scion of a wealthy southern family, but both sets of parents were appalled and managed to undo the marriage. This adventure reportedly yielded her a sizable settlement, starting her on a lifetime course of easy money.4

  At the height of the Great Depression, Virginia at seventeen left home for the 1934 World’s Fair in Chicago, where she found work: a waitress by one account, a midway shill by another, a prostitute by a third. Somehow she met Epstein, a trusted confederate of Al Capone. She came back to Bessemer, as Chick recalled, “in a factory-fresh LaSalle convertible, with her beautiful legs in shimmering silk, a fur neckpiece touching the new sheen of her hair, and more gems than a Reno pawnshop.”5

  Hill stayed long enough to dispense the gifts she’d bought her siblings, dazzle the good citizens of Bessemer, and get her brother Chick to pack. Then it was back to Chicago, where she and Chick began learning the race wire business, and seeing the money it brought in. “Joe gave it to her in damp bunches, like lettuce,” Bugsy biographer Dean Jennings wrote. “The bookie joint grew it in clusters, and there was a new crop every day.”6 Hill’s relationship with Epstein would last for years and remain enigmatic. Chick saw her treat the mob accountant with scorn. He heard her ask for more money from wherever she was, and get it by special delivery. Yet the money kept coming from Epstein even as Hill began openly dating Epstein’s fellow gangsters. Perhaps Epstein was an idealized father figure, generous to a fault even as Hill threw back the rage and hurt she had felt toward her real father.

  Clearly, business was part of the picture. Hill was entrusted to place bets at the tracks and be a courier with substantial sums. Chick would recall trips to nearby airports to pick up money sent by Epstein. As a bag woman, Hill met most of the mob’s top figures, from Frank Costello and Meyer Lansky to Longy Zwillman and Joe Doto. At Senator Estes Kefauver’s 1950–1951 hearings on organized crime, Hill would coolly acknowledge sleeping with many of her mob consorts.7

  By 1938, Hill and her younger brother had moved again, this time to L.A. They settled in West Hollywood at the Garden of Allah residential hotel, the same year a despondent F. Scott Fitzgerald lived there. Hill began making the rounds as an actress. Like Siegel, whom she hadn’t met yet, she embraced self-improvement. She loved to read Thackeray, and had a complete set of his works. She read Vanity Fair and identified with plucky, ambitious Becky Sharp and her rise from an orphanage to great wealth. In the copy that her brother Chick saw, she underscored a favorite passage. “This I set down as positive truth. A woman with fair opportunities, and without a positive hump, may marry whom she likes. I think I could be a good woman if I had five thousand a year.”8

  Becoming a film star was the twentieth-century equivalent of marrying well in Vanity Fair. With her striking good looks, and still just twenty-two years old, Hill wangled a screen test at Universal, then a seven-year contract. She was seen as a Jean Harlow type, moody and mysterious. Unfortunately, as she admitted to Chick, she had little talent, and she tore up her contract. She dined and danced at the Trocadero, the Mocambo, and the Brown Derby. Actor Errol Flynn squired her around town. They ended up in a drunken brawl at the Brown Derby, the restaurant so shaped on Wilshire Boulevard, with Hill reportedly screaming at Flynn and throwing a drink in his face.9 The Brown Derby was one of Siegel’s favorite haunts, too.

  With a limitless supply of “lettuce,” Hill took her brother on gambling trips to Acapulco. By one account, she was seen in the gambling joints so often, her red hair framing a flushed face, that the Mexican casino men gave her a nickname: The Flamingo.10 But there would be other derivations for the name of Ben Siegel’s extravagant castle in the sands.

  Passionate and willful, Virginia went home to Bessemer long enough to marry an All-America halfback and get that marriage annulled in a week. She then married, and divorced, a Mexican rhumba dancer. Unabashed, she started over in Hollywood. She threw expensive dinners at Ciro’s, inspiring one newspaper to dub her “the film city’s most generous party giver.” Social columnist Hedda Hopper wrote that “she had the swingingest parties in town.”11 Soon le tout Hollywood was mad to know who this gorgeous and mysterious young big spender was.

  Hill seems to have met Siegel in New York in 1943 or 1944. She was ensconced with “Joe Adonis” Doto in one fancy hotel or another, giving $10,000 dinners at the Waldorf Astoria. Or so she recalled to the Kefauver Commission. Was it perhaps at the Madison Hotel’s cocktail lounge that she met Siegel, the lawmakers ventured, there in the company of Frank Costello? The Madison was one of Costello’s haunts at that time, and Costello and Siegel were close. Hill said she couldn’t be sure.12

  When Hill began turning up on Siegel’s arm, there was muttering that Joe Adonis might take offense, t
riggering a gangland grudge war. Hill’s brother Chick scoffed at the thought. Joe Adonis wasn’t in love with Virginia, said Chick Hill; he wasn’t going to start a war. It was Siegel whose passions had been deeply stirred.

  As the married man in the picture, Siegel could hardly demand that Hill stay faithful to him. With her free spirit, and bundles of cash, she proceeded to act as freely as she had before she met him. She still saw Joe Adonis, whatever that meant, and rumors rolled in of late-night parties and other paramours. Siegel seethed with jealousy, but when he confronted her, Hill just laughed and swore right back at him.13 Siegel had met his match at last: Hill was as fearless as he was.

  One week, taking a break from Siegel’s jealousy, Hill stayed a night or two incognito at George Raft’s house in Coldwater Canyon. Were the two of them, his lover and best friend, consorting behind his back? The very thought drove Siegel mad, but when Hill finally surfaced, she said she had nothing to apologize for, and Raft assured his friend that Hill’s stay had been purely platonic.14

  With her endless money from Epstein, Hill was free to do as she pleased, and to sleep with whom she chose. Siegel had never met a woman so fiercely free-spirited. For the first time in his life, he was powerless. If he was like most dominating men, he probably found the experience exhilarating. Hill and Siegel were kindred spirits, both canny enough to see their chances and take them, both made of the same indestructible stuff. Surely amid Siegel’s roiling emotions for Hill was sheer admiration for the way she’d clawed her way up.