With the dawn of talkies in the late twenties, Madden began pushing Raft to give Hollywood a try. One day in 1930, the two of them set out for the Golden State together in Madden’s car. Their timing was perfect: the era of the hard-boiled gangster movie had just begun. Hollywood’s screenwriters, however, had no idea how gangsters actually talked. Raft was their answer: a Hollywood-handsome bona fide gangster. His breakthrough was the 1932 Scarface, based on the life of Al Capone. It was an instant classic, making George Raft a star. No one who ever saw him do his coin-flip trick in the movie ever forgot it.
On that first trip, Siegel spent hours at a time with Raft at the Santa Anita horse track, ruminating on how the Syndicate might muscle in on the so-called horse race wire. Gentlemen went to the track and placed their bets at pari-mutuel machines. But a whole world of off-track operators had figured out how to send race results by telegraph wire, circumventing the tracks altogether. The beauty of it was that transmitting results by wire was entirely legal. Only the bookies paying to receive those results in so-called horse parlors were committing a crime, and all they had to do was pay off the police to make everyone happy. Siegel was set on cutting the Syndicate into the race wire, whatever it took. He seemed, at the track, something of a wastrel. But he had ambitions. “Damned few people knew what made him tick,” Raft said later of Siegel. “But I did. He came out here because he wanted to be somebody.”3
In his youth, one of Bugsy’s few legal pleasures had been the nickelodeons, where he sat mesmerized by early silent film stars like Theda Bara and Rudolph Valentino. He yearned to meet the stars and studio heads whom Raft was gadding around with, but he knew he had to prove himself first. He had made a million dollars over the previous few years, he told Raft, only to lose a lot of it in the stock market. “If I had kept that million, I’d have been out of the rackets right then,” Siegel said. “But I took a big licking, and I couldn’t go legit.”4 Bugsy would have to make big money again—and build a big house to go with it—to start socializing with stars. And since the only kind of money he knew was easy money, he knew who that put him up against.
Sicilian-born Ignazio Dragna, known as Jack, had become the Al Capone of California bootlegging and headed up his own L.A. crime family, only warily affiliated with the Syndicate. Dragna had made his previous boss disappear, and would have enjoyed nothing more than to do the same with Siegel, but Lucky Luciano intervened. Siegel had the Syndicate’s blessing, Luciano told him, and Dragna would have to cooperate, as long as Siegel didn’t interfere with Dragna’s own schemes. Siegel began horning in on the racetracks, demanding cuts of the pari-mutuel pool. Nightclubs and private casinos were other obvious targets. There, in addition to dealing with Dragna, Siegel had to take on . . . the Octopus.
Casino owner Guy McAfee was a former head of the Los Angeles Police Department vice squad. They called him the Octopus because his tentacles reached into gambling, bootleg liquor, bookmaking, and prostitution, among other vices, with the city’s top politicians and police in his pocket. One of his prize holdings was the Clover Club, on L.A.’s Sunset Strip, a top-tier speakeasy enjoying the last days of Prohibition, thanks to its backroom casino, where one-way mirrors warned of impending raids so that the gaming tables could be flipped. The Clover was haute Hollywood, and Siegel wanted in. McAfee had a trigger-happy manager, Eddie Nealis, who found himself disinclined to accept Siegel’s kind offer. Nealis, in turn, had a tough enforcer on his payroll, one Jimmy Fox. Siegel had Fox shot, not quite fatally, and then went after Nealis, who somehow sensed a waiting assassin outside his home and fled to Mexico City, never to be seen on the Strip again. Part of the Clover’s nightly spoils were now funneled to Siegel by his surly new business partner, Guy McAfee.5
The following year—1934—Siegel rented a house on Arden Drive in Beverly Hills. America was flat broke, except for Hollywood, whose stars and studio heads had money to burn. With Prohibition’s end, L.A. was filled with former speakeasies now serving as bars and gambling joints. The horse tracks were packed, and the telegraph wires were burning with off-track race wire results. Meanwhile, the ex-bootleggers still had their trucks and garages, useful for drug trafficking.
Siegel’s family stayed on the East Coast in Scarsdale, which made Siegel a man about town for weeks at a time. He did his share of womanizing, and fell hard for a blonde French actress named Ketti Gallian, who had come to L.A. with a screen contract from Twentieth Century–Fox. According to Raft, Siegel spent $50,000 trying to help Gallian lose her accent. The effort was in vain. Her 1934 American debut, Marie Galante, was a bomb, and a second film did no better. Gallian went back to France, her contract bought out and her romance with Siegel dashed.6
Siegel may have felt some guilt about keeping Esther and the girls in Scarsdale through these dalliances. Probably to placate her, Ben had his sister Ethel live at the Scarsdale house to help Esther with the girls. Also, according to a U.S. census covering 1935, the Scarsdale house contained a live-in maid, a cook, and John the butler.7 All three in staff were listed as Negroes. Their presence provided not just household help, but social status in class-sensitive Scarsdale.
To anyone back in Scarsdale who asked, Siegel purported to be a sales broker with his own office.8 In L.A., he called himself a sportsman. It was a title that suggested wealth and social prominence: an owner of racehorses, or a big-game hunter. For Siegel, it was a euphemism for gambling, with a little extortion and the occasional killing thrown in. But he was reinventing himself in the town of reinvention, a most American enterprise.
The horse tracks—Santa Anita for one, Agua Caliente for another—were Siegel’s great passion and profit rolled into one. He made bets of his own virtually every day. While he sometimes lost, he more often won, thanks to the inside word he seemed to get on which horse was about to go lame, or which was doped up and likely to win. Later, a close friend would say that betting was Siegel’s main occupation by the mid-thirties and that he earned hundreds of thousands of dollars a year doing it. From all proceeds, the Syndicate took its skim: 25 percent, according to the FBI.9 As the Syndicate began building casinos in Florida—Lansky’s turf—Siegel shared in those profits as well.
Some of Siegel’s earnings at this time went to education—his younger brother Maurice’s education, that is. Maurice became an internist with a private practice in Beverly Hills. One account suggests he was, for a time, a studio doctor at Columbia Pictures.10 According to Wendy Rosen, Ben’s granddaughter, Maurice came to occupy a seat on the board of Cedars-Sinai Hospital. Years later, Maurice asked Wendy whether she knew about her late grandfather. It was the one mention of his brother he ever made to her. Ben had paid for his education, Maurice admitted, but that was all Maurice wanted to say on the subject. “If Ben came up in conversation, my aunt Lil, Maurice’s wife, would shuffle around the house,” Wendy said. “It was like he didn’t exist.”11 It was a classic scenario in gangsterland: a life of crime justified—ennobled, even—if the money could buy a family member’s escape into legitimacy. Lansky would do the same thing by sending his son Paul to West Point.
By 1935, Siegel was ready for a move up. He rented the large Beverly Hills home of Metropolitan Opera singer Lawrence Tibbett at 326 South McCarty Drive. The way the story unfolds in Barry Levinson’s Oscar-nominated 1991 film Bugsy, the house isn’t for rent. Siegel, played by Warren Beatty, just likes it as he drives by it, tells George Raft to pull over, strides in, and flashes such a big roll of bills that Tibbett is persuaded to leave on the spot. None of the more credible biographies mentions the scene, but the house on McCarty was the one to which Siegel brought his family to live.12 Unfortunately, Siegel found himself forced to make trips to New York even as he settled his family in L.A. The Syndicate had a problem for which Siegel’s help was needed.
Like Siegel and Lansky, Arthur “Dutch Schultz” Flegenheimer had gotten his start with bootleg whisky runs for Rothstein. He was a German Jew, not Dutch, but he liked his nom de crime because, as he put it, “it w
as short enough to fit in the headlines. If I’d kept the name Flegenheimer, nobody would have heard of me.”13
As the beer baron of the Bronx and the numbers boss of Harlem, Schultz was well known, so much so that he made an irresistible target for newly named Manhattan Special Prosecutor Thomas Dewey, who indicted him, as he had Waxey Gordon, for tax evasion.14 Schultz’s first trial ended in a deadlocked jury; for the second, his lawyers succeeded in moving the venue an hour’s drive north of New York to the sleepy town of Monroe, where Schultz charmed the locals and beat the rap. He came back to Manhattan bent on revenge. Dewey must die, he told his fellow gangsters. They were stunned. Did he have any idea how much heat that would bring on them? “Alright,” Schultz growled, “I’ll kill him myself in the next 48 hours.”
With that, Schultz signed his own death warrant. The gangsters resolved to dispatch him before Schultz got Dewey. And so they did, sending three of their best contract men to murder “Dutch” and his guards on October 23, 1935.15 Finding them was easy: the entourage dined every night at the Palace Chop House in Newark, New Jersey.
Dutch fled to the bathroom as the shooting broke out, so one of the killers, Charlie “The Bug” Workman, went back to finish him off. When Workman emerged, to a scene of mayhem and cowering diners, he found his fellow killers gone, along with the getaway car. Workman couldn’t believe it. He ended up walking across to Manhattan, appalled by their treachery.16 One of Bugsy’s early biographers, George Carpozi, claims Siegel was one of the gangsters Workman could blame for abandoning him.
“A little reported facet of this rub-out was Bugsy Siegel’s role in Schultz’ actual killing,” Carpozi explains. “After Lucky Luciano had dispatched [the killers] to New Jersey, he called in Bugsy. ‘Benny, you take a couple of boys and go out there to Newark. Don’t get mixed up in this deal unless [they] mess it up.’
“Thus Bugsy, accompanied by Harry Teitelbaum and Harry ‘Big Greenie’ Greenberg, waited in their parked car a short distance from the restaurant as a second line of defense,” writes Carpozi. Once they saw the first car of killers tear away, they drove off at a law-abiding speed and melted into the night.17
It’s a good story, but as with so many of Siegel’s early exploits—driving the getaway car from Joe Masseria’s murder in Coney Island, planning the killing of Salvatore Maranzano by “IRS agents,” and sneaking out of his hospital bed to put a bullet in Tony Fabrazzo’s head—it’s a story none can confirm. Gangsters rarely tell their own tales, at least not the true ones, and those who speak for them tend to embellish, until over time the story becomes a legend, even a myth. Did Bugsy Siegel really kill a dozen men himself, as he apparently told his contractor in Las Vegas? Or did he kill thirty, as the FBI suggested in an interoffice memo?
The truth of those early tales would never be parsed. Meanwhile, Ben Siegel was on his way to becoming a public figure. Increasingly his moves would be set down in type by a diligent and delighted press. There wasn’t anything Siegel could do about that but grin and hope his luck prevailed.
One of the first stars Siegel met in Hollywood was Jean Harlow, the platinum blonde bombshell who had become MGM’s leading lady in her early twenties. He met her through Longy Zwillman, the New Jersey gangster nicknamed for his commanding height, who knew Harlow’s mobbed-up stepfather, one Mario Bello. Zwillman was enamored of Harlow and procured her a two-picture deal at Columbia Pictures by giving studio head Harry Cohn a sweetheart loan for $500,000.18 Unfortunately, Harlow failed to reciprocate his feelings. Still, Harlow began coming as Zwillman’s date to dinners at the Siegel house. Siegel’s older daughter Millicent, then about five years old and on her first summer vacation in L.A., was speechless when introduced to Harlow. Soon enough, the actress agreed to become Millicent’s godmother. Not officially, since the role had no formal place in Jewish families—just informally. One of Harlow’s biographers, Irving Shulman, suggests that Harlow resented her stepfather and his crowd, including Zwillman, and tried to keep her distance, agreeing to be Millicent’s “godmother” only as a sop to an innocent girl. But Harlow enjoyed the diversions. She put on an apron and cooked; she gave Millicent baths.19
There was a seamier side to this cozy scene. Siegel was soon set on sleeping with Harlow. She had had a fling with actor Jimmy Stewart, and Siegel saw that as his way in. “Jean’s a good friend of yours,” he said to Stewart. “How about you tell her to go out with me.” To which Stewart apparently responded, “You go to hell.” Stewart told his future wife, Gloria, that he had been terrified Siegel would pull out a gun and plug him on the spot. But Stewart’s height seemed to keep Siegel from doing anything rash.20
It was, for the Siegels, a dazzling but short-lived friendship. Only twenty-six, Harlow died of a cerebral edema and uremia on June 7, 1937. The Siegels were among the hundreds who attended her funeral; according to Gloria, they were observed weeping copiously.21
The Tibbett house was suitable for modest entertaining, but it lay in the Beverly Hills Flats, below the demarcation line of Sunset Boulevard. Above Sunset was where the hills rose and the homes grew grand, with sweeping views of the valley. Siegel was set on building a house that would draw in Hollywood royalty. He bought a 1.7-acre plot on 250 Delfern Drive, above Sunset Boulevard in the Beverly Crest neighborhood of Holmby Hills. In 1937, he started building his 10,000-square-foot dream house.
That house and grounds would cost $180,000, at a time when the average cost of a home in America was just under $3,000. It would be a white-bricked, two-story structure with imposing gates and a wide, curving driveway that announced grandeur within. The front door would open into a two-story classic hall with sweeping staircase, a sixty-foot-long living room containing a piano no one could play, and a bar with a slot machine at either end. There would be an oak-paneled library, gourmet kitchen, and capacious dining room with a table to accommodate thirty guests before adding extension leaves. Siegel was enthralled. More than Lansky, he needed the trappings of wealth to prove he had come as far as he had, the Lower East Side street kid literally on top of the world he’d dreamed of entering a decade ago. This was the American dream, all right, and Siegel was proof that anyone with guts, good taste, and a gun could grab it, assuming he kept striking fear into those who might otherwise make his dream their own.
The house had twenty-three rooms in all, including six bedrooms. The master bathrooms and dressing rooms were especially striking. Ben’s was done entirely in red marble, while Esther’s had a mirrored ceiling and walls. There would be six “vanity rooms” for female guests, equipped “with crystal bottles containing exotic perfumes and comb-and-brush sets trimmed with turquoise, amethyst, silver and gold.”22
Out back, a long lap pool was being installed, along with a pool house, fountains, and formal rose gardens. Already Siegel swam almost every day to stay fit, either at the local YMCA or in George Raft’s pool in Coldwater Canyon. Soon he would use the lap pool on Delfern, along with a sprawling workout room, steam, and sauna. He was obsessed, too, with calisthenics, acquiring, after several years of daily workouts, the body of a gymnast. The whole property would be surrounded by a high wrought-iron fence and state-of-the-art security system. Some seventy-five years later, in February 2013, the house and grounds would be sold for $17.5 million to hedge fund director Jon Brooks and his wife Shanna. By December of that year, everything on the site would be gone but for the tennis court, which would soon be removed as well. Construction of a new house was under way in early 2019.23
The bills kept coming, but Siegel could afford them: almost every day, he bet up to $5,000 on horse races, baseball games, and prize fights, and almost never lost.24 As the house went up, Siegel badgered the contractor every step of the way. Often he went back again after dark, with George Raft in tow, the two of them lighting wooden matches so that they could inspect the progress.
One night, with the house far along, Siegel brought Raft to the master bedroom. As Raft later explained, the wall beside the bed had a sliding panel co
ntrolled by a concealed button: a trapdoor, like a dumbwaiter. “Who needs it?” Raft teased.
“I do,” Siegel retorted. “I got two others in the house. Maybe some day I gotta get out of here in a hurry.” In the library, a set of fake bookcases slid open to reveal cabinets and a safe in which he kept his jewelry, papers, and two guns: a Smith & Wesson .38 caliber revolver and a .38 automatic.25
Cheering on the project was a wealthy woman whom Esther Siegel must have resented, for Siegel soon became her man about town.
Dorothy di Frasso, born Dorothy Taylor, had inherited $10 million from her father’s $50 million New York leather goods company. She had had one failed marriage—to famed English aviator Claude Grahame-White—and one unhappy, ongoing one, to a destitute but titled Italian much older than she. Count Carlo Dentice di Frasso lived in a sprawling villa on the outskirts of Rome and spent his wife’s money. Dorothy, in exchange, became the Countess Dentice di Frasso, often apart from her husband for weeks at a time in Beverly Hills, entertaining at her own mansion on North Bedford Drive. According to society columnist Elsa Maxwell, the countess set up a boxing ring at her first major party and staged three bloody bouts. Maxwell said of di Frasso that she had a “racy wit, did the most outrageous things.”26
Di Frasso had just ended an affair with Gary Cooper when she looked over from her box at the Santa Anita track and saw a handsome stranger marvelously dressed.27 She decided, moments after meeting Ben Siegel, that he was a perfect successor to the screen idol. At di Frasso’s next dinner party, Hollywood journalist Florabel Muir was shocked to see Siegel and di Frasso heading up the receiving line together. “She gave spectacular parties,” reported Louella Parsons, another well-known society chronicler. “She wore magnificent jewels.” At one party, Parsons related, di Frasso put Dictaphones under the chairs and divans, “and the upshot was that guests heard their supposedly best friends commenting caustically on their clothes, boy friends, and peccadilloes, all of which was highly amusing to the hostess, but spread social havoc among the hapless victims.”28
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