
In 1989, Donald Trump

That year, Donald had launched the brand new Trump: The Game. It was a game that sought to simulate the dynamics of the real estate world. Each player started with initial capital and could buy properties. Whoever ended up with everything won. Very similar to the popular Monopoly. Trump himself had described it as “a game that defines whether you have what it takes to succeed in business or not”.
At that time, Bob Stupak seemed to be obsessed with Donald Trump. He followed him to practically everywhere and used the tycoon’s growing public image to generate publicity for his own casinos. In fact, they even competed for the same site, located in Atlantic City, although Donald ended up withdrawing from the casino market after a few failures.
It was in this context that Stupak decided to publish a full-page ad in the New York Post, challenging Donald Trump to a game of his own game, with US$1.000.000 dollars on the line. The audacity was such that a refusal from Donald seemed almost impossible. However, the current head of state ignored the matter.

A Representation Of The Million Dollar Challenge Ad Published By The New York Post
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“I saw Donald Trump on Entertainment Tonight a couple of weeks ago,” Stupak told local news. “He said it’s a game that will tell you if you have it or not. Well, I thought it would be a good opportunity to see if he has it or not.”
However, Trump was not intimidated by the newspaper publication or the statements of his challenger.
“This is another example of someone who wants to make a splash using the Trump name. I have no intention of sitting down with someone I don’t know to bet a million dollars on a game designed to raise funds for charity,” Trump stated bluntly. “It would be absurd,” he concluded.
Ultimately, the meeting never happened and Trump: The Game ended up being a huge sales failure. Perhaps, if he had accepted the bet, the publicity would have done him good, although it could have ended up costing him dearly. As if that weren’t enough, Bob Stupak launched his own game: Stupak: The Ultimate Game of Skill and Chance. The game was nothing like Trump’s and neither were the sales, as Stupak’s game was successful.
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