Donald Trump, a name synonymous with wealth, risk, and controversy, has lived a life filled with high stakes – both in politics, business and gambling.
While many recognise him as a former and the incoming President of the United States, fewer know about his audacious and larger-than-life escapades in the gambling industry.
In this article, we take a deep dive into some of the most outrageous, captivating, and sometimes downright bizarre Donald Trump gambling adventures that showcase his knack for embracing risk, courting rivalry, and leaving a mark – win or lose.
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Bankruptcy: The Rise and Fall of Trump’s Casino Empire
Donald Trump’s persona has always been that of a successful man, whether in business, his personal life, or his foray into politics, as aptly demonstrated by his recapturing of the White House.
However, while Trump may project an image of unbroken success, he’s also faced significant challenges and monumental failures. Nothing illustrates these setbacks better than his ventures into the casino industry.
Back in the 1980s and 1990s, Trump’s foray into gambling seemed poised to redefine Atlantic City.
With his larger-than-life ambitions, Trump opened several lavish casinos bearing his name. From the dazzling Trump Taj Mahal to the Trump Castle, his empire was a testament to his audacious vision.
Yet, while Trump revelled in the prestige of having his name atop Atlantic City’s skyline, his properties faced financial challenges that ultimately ended in bankruptcy.
A quick roll call of Trump’s Atlantic City Casino ventures:
- Trump Taj Mahal – Promoted as the “eighth wonder of the world,” this palace of excess declared bankruptcy not long after its grand debut.
- Trump Plaza Hotel and Casino – A symbol of early success, it later succumbed to the industry’s ruthless tides.
- Trump Marina – Eventually sold off, marking another setback in his casino aspirations.
- Trump Castle – Royal in name, it too faced turbulent times.
- Trump World’s Fair Casino – It promised grandeur but delivered disappointment.
These casinos were opulent and ambitious, but they also came with towering debts and operational challenges.
Over time, each of these properties declared bankruptcy, leaving Trump with a legacy as a failed Casino boss.
While his gambling didn’t pay off in this instance, Trump leveraged these ventures to catapult himself into the public eye.
His boldness in putting his name on every venture turned him into a household name, paving the way for reality TV fame and his eventual political career.
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Betting on the Presidency: A Gamble That Paid Off
When Donald Trump announced his 2015 presidential bid, many dismissed it as a publicity stunt. Pundits laughed, critics scoffed, and even the gambling markets weren’t quite sure how to price his odds.
But as he bulldozed his way through the primaries, the betting markets began to buzz. By the time the 2016 election rolled around, Trump had become one of the most hotly debated – and bet-on – figures in political history.
Even then, he was still widely expected to lose the general elections. But by the time the 2016 election concluded, those who bet on Trump against the odds were laughing all the way to the bank as he pulled off one of the most stunning electoral upsets in American history, sending shockwaves around the world.
However, the tables turned in 2020 when Trump’s polarising political persona made his re-election bid unsuccessful despite being touted as the likely winner by many commentators.
Never one to accept defeat, Trump once again beat the odds to regain the White House this year, leaving the gambling world spinning and cementing Donald Trump as the ultimate gambling wildcard.
For punters who placed early bets on his victory, the rewards were jaw-dropping.
Against all odds, Trump defied conventional wisdom to win not once but twice, making those bold enough to back him significantly richer.
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The Gambling Samurai: Donald Trump vs Akio Kashiwagi
One of the most intriguing tales from Trump’s gambling past involves his showdown with Akio Kashiwagi, a mysterious, high-stakes gambler from Japan and one of the most enigmatic figures in Japanese gambling lore.
Known for his extraordinary skill, confidence and astronomical bets, Kashiwagi was the type of player who could put casinos on their toes.
At one point, Trump challenged Kashiwagi to a series of games. Trump initially came out on top, basking in his triumph.
But Kashiwagi, ever the competitor, demanded a rematch – and this time, the tables turned. He walked away with a hefty sum, leaving Trump with an eye-watering debt.
Before Trump could pay up, however, Kashiwagi tragically met an untimely end in Japan, reportedly linked to the Yakuza and the country’s gambling underworld.
While Trump was not implicated, the tale adds a dramatic, almost cinematic chapter to his gambling history.
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Trump the Forgetful: Losing Track of $700,000
If there’s one story that perfectly encapsulates Trump’s peculiar approach to business, it’s the time he forgot about losing $700,000. Not exactly a ringing endorsement of someone whose businesses are supposedly about money, numbers and statistics.
It’s little wonder, then, that his casino and gambling ventures were a colossal failure.
According to former executive John R. O’Donnell, Trump was informed multiple times about the $700,000 loss, but each time, it seemed to slip his mind.
When he finally realised the scale of the deficit, he exploded in characteristic Trumpian fashion, demanding to know how such a loss could happen.
While some might chalk this up to his infamous attention to detail (or lack thereof), others might see it as a man preoccupied with bigger pictures—whether that’s real estate, television, or global politics.
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Donald Trump Gambling Adventures: Rivalry with Steve Wynn
No list of Trump’s gambling escapades would be complete without his rivalry with fellow casino magnate Steve Wynn.
While Trump ruled Atlantic City, Wynn was the undisputed king of Las Vegas, with iconic properties like the Mirage and Bellagio to his name. The two were ambitious, competitive, and determined to outshine each other.
Though they clashed in business, their relationship eventually softened, evolving into a kind of begrudging respect.
According to Trump, many of his critics – Wynn included – had, at one point, sent him private letters of admiration.
It’s a classic Trump move to turn rivals into reluctant allies, blending business savvy with showmanship.
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What These Gambling Stories Say About Donald Trump
Love him or loathe him, Donald Trump’s gambling stories reflect the man himself: audacious, unpredictable, and endlessly entertaining.
From casino bankruptcies to betting on his political future, his approach to risk has shaped his persona as one of America’s most enigmatic figures with an uncanny ability to spin even the most outrageous situations into a narrative that serves him.
So, whether you’re a fan of casinos, sports betting or politics, Trump’s escapades in the gambling world offer plenty of food for thought.
After all, what’s life without a little gamble?
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Feeling Inspired? Try Your Hand at Online Betting
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And make sure to explore our betting guide for the best gambling strategies, because, honestly, you’ll want to make better gambling decisions than Donald Trump.