So picture this: sometime in the late 1980s, Donald Trump — then an Atlantic City casino magnate constantly generating national headlines for himself — releases a Trump-branded board game called “Trump: The Game.” Bob Stupak watches this happen from across the country in Las Vegas and, rather than shrug it off, decides the correct response is to build his own board game, put his own name on it, and publicly challenge Trump to a million-dollar charity match playing it. Trump declined. The whole episode lasted about as long as it takes to read this paragraph, and it’s exactly the kind of stunt that made Bob Stupak Bob Stupak.
“Stupak: The Ultimate Game of Skill and Chance”
The game itself was real, and it still exists — copies of “Stupak: The Ultimate Game of Skill and Chance” turn up regularly on eBay today, sold as vintage Las Vegas collectibles, sealed-in-box editions marketed toward casino memorabilia hunters rather than anyone actually looking to play a board game on a Friday night. It was designed as family entertainment, simplified enough that beginners could pick it up without knowing the rules of actual casino games, built around the same “skill and chance” framing that defined Stupak’s own approach to everything from poker to Super Bowl bets. It never became a cultural fixture the way Trump’s game briefly was. But it outlasted the challenge that inspired it by decades — you can still buy one today, more than a quarter-century after Stupak first put it on the market, a small physical artifact of a beef that otherwise exists only in newspaper archives and obituaries.
Two Minutes With the Globetrotters
The Trump challenge wasn’t an isolated stunt; it was one entry in a much longer pattern of Stupak treating publicity as a competitive sport with its own rules and its own scoreboard. In one of his most-repeated stunts, he paid the Harlem Globetrotters $100,000 for the chance to play alongside them in an actual game — for two minutes. Some retrospective accounts inflate the framing into a $100 million charitable pledge to the United Negro College Fund in exchange for the same privilege, but the more consistently sourced version, including his own Las Vegas Sun obituary’s tally of career highlights, puts the figure at $100,000 for two minutes of court time — itself already an absurd number for such a short appearance, and exactly the kind of self-inflating exaggeration that tends to accumulate around a showman’s legend the longer he’s gone. Both versions agree on the shape of the stunt even if they disagree wildly on the price tag: Stupak paying real money for the specific, photographable image of himself doing something no other casino owner in town would think to do.
The same instinct produced one of his most notorious paydays-in-reverse. When Vegas World’s new tower opened, Stupak offered a stuntman $1 million to jump a motorcycle off the building onto a cushion below — then, once the stunt was done and the check was written, charged the stuntman a $990,000 “landing fee.” The stuntman walked away with $10,000 for jumping a motorcycle off a Las Vegas hotel tower, and Stupak walked away with a story that ran in newspapers for exactly the reason he wanted it to.
Losing at Poker With a Supercomputer, and Winning at the World Series
Stupak’s promotional instincts extended into his actual gambling too, in ways that blurred the line between “competing” and “performing.” In 1989, the same year as the Super Bowl bet, he played a nationally televised game of no-limit poker against a supercomputer for $500,000 — and won, a result that generated exactly the kind of “man beats machine” headline that suited him perfectly, regardless of how seriously anyone should take a single hand of televised exhibition poker as a measure of anything. He was also, underneath all the stunts, a genuinely capable poker player: he won a World Series of Poker bracelet in the $5,000 buy-in no-limit deuce-to-seven championship in 1989, took home $139,500, and made three more WSOP final tables over the course of his career, along with a final table appearance in the first season of the World Poker Tour years later. High-stakes poker player Mike Sexton, recalling Stupak after his death, told a story of Stupak once challenging Alaska gambler Perry Green to a heads-up match on a Concorde flight home from a poker trip — and then, once back in Las Vegas, publicly announcing he’d just played in the highest-stakes poker game of all time.
The Pattern
None of these stunts, on their own, would be remarkable. Casino owners have always chased publicity. What made Stupak different was the sheer volume of it, and his apparent inability to distinguish between a genuine competitive impulse and a marketing opportunity — or, more likely, his total disinterest in distinguishing between the two at all. The Trump board-game challenge, the Globetrotters payment, the motorcycle jump’s fake landing fee, the supercomputer poker match: each one is a slightly different flavor of the same move, repeated across three decades, until “pulling a Stupak” became its own kind of local shorthand for a publicity stunt built entirely around the gap between how something looked and what it actually cost or paid out.