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

Let our journalists help you make sense of the noise: Subscribe to the Mother Jones Daily newsletter and get a recap of news that matters.

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.

Read the rest of “The Trump Files”:


Headshot of Editor in Chief of Mother Jones, Clara Jeffery

It sure feels that way to me, and here at Mother Jones, we’ve been thinking a lot about what journalism needs to do differently, and how we can have the biggest impact.

We kept coming back to one word: corruption. Democracy and the rule of law being undermined by those with wealth and power for their own gain. So we're launching an ambitious Mother Jones Corruption Project to do deep, time-intensive reporting on systemic corruption, and asking the MoJo community to help crowdfund it.

We aim to hire, build a team, and give them the time and space needed to understand how we got here and how we might get out. We want to dig into the forces and decisions that have allowed massive conflicts of interest, influence peddling, and win-at-all-costs politics to flourish.

It's unlike anything we've done, and we have seed funding to get started, but we're looking to raise $500,000 from readers by July when we'll be making key budgeting decisions—and the more resources we have by then, the deeper we can dig. If our plan sounds good to you, please help kickstart it with a tax-deductible donation today.

Thanks for reading—whether or not you can pitch in today, or ever, I'm glad you're with us.

Signed by Clara Jeffery

Clara Jeffery, Editor-in-Chief

payment methods

We Recommend