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History: The Woman Who Asked for Too Much

Virginia Hill
Everett Collection Inc./Alamay Stock Photo

Virginia Hill’s savvy and sophistication made her more than a pretty mob moll

Whenever the name “Virginia Hill” surfaces, it’s always quickly followed those of Bugsy Siegel and the Flamingo. It’s ironic that a woman who maintained her independence in the male-dominated world of the Mafia is known as a “girlfriend of.” It’s even more ironic that she’s best-remembered in a town she hated by a casino that wasn’t actually named after her.

Virginia was a backwoods waif who became a gossip-column celebrity, and the only woman who sat at the table with the Mafia, moving between the Chicago, New York, and Los Angeles outfits for nearly two decades. She transported stolen property, fixed racetrack odds, negotiated deals, laundered money, paid bribes — all under the guise of a “Georgia oil heiress” or “Manhattan glamour girl,” as The New York Journal-American variously called her. Her life was a mix of glamourous spotlights and violent backrooms. She could disarm hair-trigger muscle without raising a hand, and get more information from a man with a word and a wink than brass-knuckled goons could beat out of him. Cold-blooded mob murderers feared her sharp tongue. Yet she was also known for her kindness: “She was likable, friendly, sympathetic and genuinely big-hearted. No appeal for help ever went unanswered,” Lee Mortimer wrote in Chicago Confidential. Virginia remained untouchable — until the fallout from her 1951 testimony before the Kefauver Committee made her the most glamorous figure to ever appear on a “Wanted” poster.


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Fighting Back

She was born in August 1916 in Bessemer, a busted-out Alabama boomtown. Virginia was the seventh of 10 children in the kind of white trash family that peaks at Faulkner and taps out at Jerry Springer. She was a timid, ginger-haired child who’d scrounge pennies to buy other children candy. Her father, Mack Hill, was an alcoholic ex-horse trader who took out his disappointments on the members of his family — except one. One night, Mack staggered home, drunk, slurring insults and shaking fists. When he advanced on his 8-year-old daughter, Virginia grabbed a skillet full of bacon grease off of the stove and slammed it into her father’s chest. He fell to the floor, howling in pain, and the little girl learned something that would serve her well in years to come: Scratch a bully and you’ll find a coward. And whatever happens to you when you fight back cannot be worse than what happens to you if you don’t.

If that was the day Virginia Hill left childhood behind, it took a few more years for her exterior to catch up. She blossomed into a leggy redheaded beauty and quit her small town shortly thereafter — it was said she married a much older man who died or divorced or just left. It is the first time Virginia disappears and reappears from her own life story, but it won’t be the last.

She resurfaces in Chicago in the summer of 1933, just in time for the World’s Fair. The “Century of Progress” was a 17-month celebration of a prosperous, harmonious world … a world in which the Reichstag fire had just burned out Germany’s last resistance to Hitler and one out of four Americans was unemployed. Millions came to wonder at a seven-story Chinese temple, cheer the Major League Baseball’s first All-Star game, and ogle burlesque dancer Sally Rand.

Virginia found a gig waitressing at one of the Fair’s Italian restaurants, the kind of place where mobsters enjoyed a plate of gnocchi and a glass of red before shaking down souvenir stands and counting the take at the whorehouses. Some made plays for the curvaceous doll with the drawl, but Virginia gave all of them the brush-off. Except one. Joey Epstein wasn’t your typical mobster, a mild-mannered accountant in a world of flamboyant thugs. He tipped Virginia extravagantly, wisecracked with her, and began escorting her to mob parties, where she arrived on his arm but always worked the room. As he introduced her around, he discerned that Virginia could be useful: Sexy, smart, streetwise, she was motivated by money, but it didn’t blind her. She liked the fellas, but she wouldn’t make a sap of herself.

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The two weren’t a couple. Actually, there had been talk that Epstein was gay, but the presence of his buxom, bawdy companion silenced it. The pair were friends and business partners: Epstein mentored her in a manner that was equal parts Goodfellas and My Fair Lady. She set aside the tacky finery of a hick-town teen for cashmere sweaters, tailored suits, and pearls by day, flamboyant couturier evening gowns by night. “There was nothing sleazy or poor-white about Virginia Hill. Somewhere along the line, her money and some mysterious inner instinct had combined to give her impeccable taste,” according to columnist Carl King.

But the taste for finer things didn’t stop there. Virginia’s homes were furnished with fine antiques, bone china, fine crystal. She sought to improve herself with gourmet cooking classes, French lessons, a leather-bound library full of Shakespeare and Thackeray. The latter’s Vanity Fair was her favorite book; how could she not identify with its heroine, Becky Sharp, another redhead from humble means who sought to rise in society by any means necessary?

Virtually every week, Virginia lounged in deluxe round-trip accommodations on the Twentieth Century Limited express train, luggage bulging with diamonds and furs that might have been bought at a Manhattan boutique — or stolen from a Chicago matron. Fittingly for a “bag woman,” Virginia was known for enormous purses, crammed with matchbooks from Ciro’s and the Copa, platinum lighters and gold compacts, poems, phone numbers — and, of course, wads of hundreds, perhaps a thick envelope destined for a Florida senator, California union organizer, or Guadalajara businessman.


The Partnership

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In 1937, one of those trips from the Windy City to the Empire State lasted much longer than a weekend. The Chicago mob had formed a tentative partnership with the mafiosi of New York, and wanted to be sure their new associates were keeping up their end of the bargain. Thus Virginia Hill moved her sables and cash into a hotel suite, and set her sights on NYC don Joe Adonis, who fell fast and hard. It never occurred to him that such a catch might come, well, with a catch: Virginia reported his every word and action back to the boys in Chicago.

She and Adonis tore up the town, the Chicago mob was happy, the dough was rolling in — and then, in a bar in Brooklyn, she met Ben Siegel. Tall, blue-eyed, a fan of daily workouts and custom tailoring, Siegel was unlike the swarthy, pasta-plump mobsters and gray-haired sugar daddies Virginia was used to cozying up to. The chemistry was instant, and the two went home together that night, Joey A or no Joey A.

And, abruptly as she had arrived, Virginia left New York. She spent some time down south, bought her mother a house, packed her younger brother Chick into her Cadillac and headed west. In summer 1938, Virginia hit Hollywood, moving in on her third mob outfit as she quietly befriended Los Angeles vice king Jack Dragna. More publicly, she took up with actors Errol Flynn and George Raft, as well as drummer Gene Krupa and budding movie mogul Carl Laemmle Jr. Her gowns were by designers-to-the-stars like Howard Greer and Irene; she got her hair done at Perc Westmore’s salon, where Carole Lombard and Lauren Bacall got their tresses tended to and where she dazzled the staff with $50 tips. At parties, she joked with Groucho Marx, clinked glasses with Ava Gardner. Modern Screen gushed, “Her parties are reminiscent of something that went out with the Romans. ... One evening she rented the Mocambo and its entire staff for a shindig. Conservative estimates say that little social cost her well over $3,000.”

Virginia also began spending a lot of time in Mexico. She seemed another gringa on a spree, partying at the racetracks and nightclubs. But Virginia’s pursuit of pleasure hid business: to facilitate the Mafia’s control over the flow of narcotics from Mexico. She became a star of Mexico City’s high society, but was also seen in the back of local cantinas, huddled in conversation with mysterious men.


A Flamingo Is Born

It was around this time that Virginia acquired her nickname, “Flamingo” — some said for her long legs, others for her reddish hair, others for the reddish tint her skin took on after she’d downed too many cocktails. The mob kept her crisscrossing the map, although she stopped back in Alabama long enough to marry and annul a local football hero. In Hollywood, Virginia Hill and Ben Siegel crossed paths once more ... and this time they stayed crossed. The pair were matched in many ways, an odd couple in others. He went to bed early, she partied all night. He was a teetotaler, she could down a dozen drinks in an evening. But both shared hot tempers, high sex drives, and a taste for life’s finer things.

In 1940, Virginia signed a contract with Universal Pictures, and brother Chick tagged along to her acting classes. She screen tested for Ball of Fire. It’s not hard to imagine her in the B-girl lineup behind Barbara Stanwyck — and IMDB credits her with an “uncredited” role as a hat-check girl in Manpower, starring her old friend George Raft. But Virginia soon lost interest. Chick said his sister “just chickened out. … She knew neither of us had any real talent and it was too much work.”

Over the next few years, Virginia and Ben maintained their affair despite other involvements, sparking fights and reconciliations that seemed like passion. Siegel juggled his wife and actresses Wendy Barrie and Marie McDonald; Virginia had another fling with Joe Adonis, then dallied with a dancer named Miguelito Valdes, spontaneously marrying him to avoid hassle at the border. She headed back to New York for another money-laundering opportunity as a partner in the Hurricane Club. The jazz spot’s logo featured a voluptuous redhead, naked save for an artfully placed palm frond, and its tropical-themed room was the site of many a legendary Duke Ellington gig.

Conversely, Ben Siegel’s new project didn’t make money. Instead, he seemed to be pouring it into a bottomless hole in the desert. It wouldn’t be the first casino in Las Vegas or Siegel’s first casino in Las Vegas. Hell, it wasn’t even his idea. The Flamingo originated with Billy Wilkerson, founder of The Hollywood Reporter and owner of Ciro’s, among other hot spots, who wanted to bring the glamour of Hollywood and Monte Carlo to Vegas. The New York mob bailed him out of some financial trouble, and soon Wilkerson was out and their boy Ben Siegel was in.

Siegel didn’t see the Flamingo as just another betting wire or nightclub to oversee. He made it a personal project, involving himself in every detail from the imported palm trees by the pool to the handmade leather trash cans in the rooms. He spent money like it wasn’t real — $115,000 to enlarge a boiler room, a million to redo the guest-room plumbing. Ben hoped his luxury casino would entice gamers to part with their money but, in truth, no one gambled more on the Flamingo (or lost bigger) than the man who built it.

The idea of a glitzy casino named after her (intentionally or not) initially piqued Virginia’s interest, but Las Vegas left much to be desired. She was allergic to cactus, and it seemed as if she got sunburn as soon as she stepped outside. Her “Baby Blue Eyes” was more interested in playing mogul than lover, and so Virginia sat in the darkened lounge or his bulletproof suite, drinking Stinger after Stinger, turning up the radio to drown out the hammers and drills. Their relationship was already troubled, but the Flamingo accelerated its downhill slide.

Slipping out of a bad situation was likely one of the reasons Virginia began making trips to Europe — “to buy wine for the Flamingo,” as she used to claim. But she also made stops in Switzerland, home of the anonymous bank account. It was assumed she was running errands for Joe Epstein as usual, but there is also speculation that she may have been on a similar mission for Siegel, suitcases filled with cash skimmed from construction funds and decorating budgets.

The Flamingo was nowhere near ready for its December 1946 opening — but that didn’t stop Bugsy. He planned a glitzy launch weekend. Jimmy Durante was hired to headline, the staff was dressed in white ties and tails, and a new runway was built to accommodate the movie stars flying in on private planes.

It didn’t go as planned. Studio heads told their actors to steer clear of the resort; those who were willing to defy Goldwyn or Mayer were kept in California by torrential rains. Virginia drifted though the casino in a flamboyant pink-and-orange gown that cost $3,000, but she didn’t really mingle — Ben was the one enthusiastically greeting every B-list actor and local politico who turned up. In the meantime, slick players and tricky dealers took the Flamingo for hundreds of thousands of dollars and, by Monday, the showroom and casino were empty. Siegel’s Taj Mahal had turned into a total joke. He closed for two months and staged another re-opening in the spring, but the property still struggled.

Gone Girl

And suddenly … Virginia was gone. Maybe she got an official warning as a valuable employee, or perhaps it was a quiet tip from Ep or Joey A. to an old friend. Maybe her instincts told her to clear out. But she put an ocean between herself and Ben Siegel and, on June 20, 1947, she proved wise to have done so. Bugsy Siegel was shot to death in Los Angeles, sprawled on a chintz sofa in Virginia’s living room.

She got the news while holed up at the Ritz with the heir to a French champagne fortune. Asked about her former paramour, she swung between tears and tough talk: “Yes, I loved him. But he wasn’t in love with me or any woman. All he cared about was that goddamn Flamingo.” Virginia attempted suicide in Paris and Monaco before returning to the United States in August 1947, declaring to the press that, “I can take care of myself. I’ve been doing it for 30 years and I can keep on.”

As the ’40s turned into the ’50s, Virginia toured the resorts of the Southwest and eventually wound up in Sun Valley, where she hooked up with ski instructor Hans Hauser in 1950. The pair met in February, married in March and became parents in November. Four months after son Peter was born, Virginia was summoned to appear on the hottest TV show in America: The Kefauver hearings on organized crime.

If the flashbulbs of café society had seemed impertinent, they had nothing on the paparazzi awaiting her as her taxi pulled up to the courthouse in lower Manhattan. “The fabulous sweetheart of the slain Bugsy Siegel,” as the newsreels called her, wore a silver fox stole and a defiant smirk. Taciturn Frank Costello, vicious Lucky Luciano, sly Meyer Lansky — those were Mafia masterminds. But this sassy redheaded dish? The Committee was just pumping her for pillow talk, as she gave evasive denials to questions like, “Have you ever known anybody in the narcotics traffic in Mexico?” Virginia played the “dumb doll,” telling Kefauver, “I don’t care anything about business in the first place. I don’t understand it.”

When she sashayed out of the courtroom, Virginia thought she had handled the senators with the same skill she had managed the mob. But rather than avoiding disaster, she had walked right into it. The government began deportation proceedings against Hans. Then the IRS slapped Virginia with a bill for $130,000 in back taxes and seized her home, leaving her standing on the porch, peering into her own windows. The government put everything from kitchen utensils to diamond bracelets on the auction block, but Virginia was long gone, apparently slipping across the southern border under the protection of a friend with a diplomatic passport.

Throughout the 1950s, the family wandered the globe from Hong Kong to Paris, traveling in a pair of Mercedes-Benzes, staying in the finest hotels, where increasing amounts of liquor helped Virginia ignore the disdainful stares and whispers about “Frau Gangster.” Her money machine continued pumping out $100 bills by the stack. She still made regular trips to Switzerland. Was she making withdrawals from an old Siegel account? Was the mob still paying her? Was it for her services —or her silence?

But as the ’50s turned into the ’60s, finances took a turn for the uncertain. Hans drifted away to teach skiing on some other slope, Virginia lived in a small hotel, where her teenage son worked as a waiter. She put out some feelers about whether the U.S. government would let her come back, but the judge who was negotiating the deal died suddenly. Vague items appeared in magazines about her publishing a memoir. She reached out to old associates and made mention of needing money, of a diary.

On an early spring day in 1966, she suddenly headed to Naples to meet the now-exiled Joe Adonis. Several days later, she was found in the woods near Salzburg, dead from an overdose. “I can’t understand why my mother died so suddenly and under mysterious circumstances,” her son told UPI.

Dangerous men gave Virginia Hill secrets to keep, and she built a life on those secrets. She, of all people, knew that surrendering those secrets could mean surrendering her life. But Virginia Hill had always pushed her luck — right up to its limit. Perhaps it wasn’t hard to understand that one day, that luck would run out.