So picture this: Pittsburgh, the early 1950s, and a young boy is watching his father run an illegal floating craps game called the Lotus Club — a racket Chester Stupak operated for more than fifty years, in part by paying off local police to look the other way. His son Bob is unimpressed by school and thoroughly impressed by his father’s antics, and by his teenage years he’s already running his own small-time operations: a backroom card game, a bit of loan-sharking, selling watches on the side. Motorcycle racing becomes his other obsession — he competes as far away as Florida and, at one point, ranks third nationally — until a near-death crash on the racing circuit eventually pushes him toward something quieter. This would not be his last motorcycle crash, and it would not be his last brush with mortality either, but it’s the first documented one, decades before the Stratosphere and the coma that nearly ended everything.
Bobby Star
At nineteen, restless and looking for a new identity, Stupak reinvented himself as a nightclub singer under the stage name Bobby Star, playing clubs and landing an actual recording contract with United Artists. His singing voice, by every account that survives, was mediocre at best — one obituary put it bluntly: “He couldn’t sing” — but that never stopped him from cutting a Christmas record called “Jake the Flake” or from working the identity for whatever it was worth. Decades later, long after Vegas World and long after the Stratosphere, Stupak would still occasionally slip back into the Bobby Star persona for an audience of one: journalist and longtime Stupak chronicler recalled an evening at Stupak’s home where, unprompted, a grown man in his fifties or sixties suddenly started crooning old standards to Phyllis McGuire — the former McGuire Sisters singer who was, by then, the great romantic relationship of his life — finishing with a line from “Our Love Is Here to Stay” that landed exactly as intended. Stupak, asked directly why he’d told him about Bobby Star, allegedly went the color of someone whose secret had just been correctly guessed. It might be the single most human moment on record involving a man who spent most of his public life performing bravado instead.
Coupons, Australia, and a Second Act
The singing career went nowhere financially, and by his early twenties Stupak had pivoted again — this time toward something that would actually make him money: two-for-one dinner coupon books, sold to restaurants as a way to drive traffic. He moved the business to Australia in the mid-1960s, expanded into telemarketing, and built enough of a stake there to eventually bankroll his return to the United States — though not without controversy; he was reportedly evicted from Australia amid allegations of questionable business practices, a pattern that would repeat itself throughout his career on a much larger scale. He came back to Las Vegas in 1971 with roughly $300,000 in the bank, bought a restaurant, quickly discovered restaurant ownership wasn’t his calling, and pivoted one more time — toward a Nevada gaming license, and the string of casinos that would define the rest of his life.
The Vault, and Vegas Vicky’s Other Match
Before Vegas World became his signature property, Stupak dabbled elsewhere downtown. He bought the Sinabar lounge and renamed it The Vault. And in one detail that connects directly to one of the Strip’s other enduring neon love stories, Stupak leased the Glitter Gulch property on Fremont Street and erected the neon sign of “Vegas Vicky” — a cowgirl figure conceived, in Stupak’s version of the story, as a potential mate for the already-famous Vegas Vic sign glowing over the Pioneer Club a few blocks away. The Vicky sign that eventually got formally “married” to Vic in a staged 1994 street ceremony had a slightly more complicated commercial lineage than that single romantic framing suggests — she’d already been installed above the Golden Goose casino years earlier, initially nicknamed Sassy Sally — but Stupak’s own hand in the Glitter Gulch chapter of her story is one more small, easily overlooked thread tying his career into the rest of the Strip’s neon folklore, decades before anyone staged an actual wedding for the two signs.
The Zsa Zsa Years
By the time Vegas World’s showroom was up and running, Stupak had enough pull to book Zsa Zsa Gabor as a headliner — a small but telling sign of how far the coupon-and-craps kid from Pittsburgh had come from his father’s illegal Lotus Club. It’s the version of Bob Stupak most people who only know the Super Bowl bet or the Stratosphere never hear about: the teenage hustler, the failed pop singer, the coupon salesman exiled from Australia, all of it happening years before he ever set foot in a suitcase-carrying sportsbook or watched a tower he built nearly burn down before it opened. Everything that made him famous in Las Vegas was, in a real sense, just the biggest and loudest version of a hustle he’d been running, in one form or another, since he was old enough to sell a watch on a Pittsburgh street corner.