The Trump Files: Donald Once Turned Down a Million-Dollar Bet on “Trump: The Game”

“It’s always possible to lose, even for someone who’s used to winning,”

Ivylise Simones


Until the election, we’re bringing you “The Trump Files,” a daily dose of telling episodes, strange-but-true stories, or curious scenes from the life of GOP nominee Donald Trump.

“It’s a much more sophisticated game than Monopoly,” Donald Trump said when his new board game, “Trump: The Game,” debuted in 1989. (Note: It’s not.) So sophisticated, in fact, that Trump admitted that even he sometimes lost. “I’ve done very well at the game…but on occasion, I got clipped,” he said at the game’s announcement in February.

Bob Stupak, a Las Vegas casino owner, was apparently listening. A month later, he challenged Trump to a head-to-head “Trump: The Game” battle for a $1 million prize, announcing it via a full-page ad he ran in the New York Post and the Press of Atlantic City.

Stupak told his local NBC station, KSNV, that he was generously giving Trump a chance to profit off the Stupak name. Stupak had recently earned fame for winning a $1 million bet on that year’s Super Bowl. “I’m not looking to ride on Donald Trump,” he said. “I’m giving him an opportunity to ride on my reputation. I’m the one who makes the large wagers, or has a history of doing it. And also to give him an opportunity to try to promote his new game.”

Trump, sadly, said no. “It’s always possible to lose, even for someone who’s used to winning,” he told the New York Post.

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