Donald Trump: The King of Failed Gambles

5 min readSep 29, 2024

Donald Trump — Mr. Real Estate, The Apprentice star, and former President — sure knows how to make a mess of business ventures. You want failures? He’s got them in bulk. Let’s dive in.

New Jersey Generals: The Football Fiasco

Trump bought the New Jersey Generals in the ’80s, part of the USFL. Why? Because the NFL told him, “No thanks.” So, what does Trump do? He goes all in, pushing the USFL to compete directly with the NFL. This brilliant strategy led to an antitrust lawsuit. The USFL won, but — here’s the punchline — they were awarded a whopping $1. That’s right, the NFL crushed the USFL, and Trump helped nail the coffin shut. Genius move, Donny!

Trump Steaks: Overcooked, Overpriced, and Over

In 2007, Trump cooked up Trump Steaks, because who wouldn’t want overpriced beef from a real estate mogul? Sold exclusively through Sharper Image (yeah, because that’s where people go for gourmet beef), the steaks were tougher than his presidential debates. After two months of bad reviews and no sales, they pulled the plug. Guess people didn’t want to pay $50 for a slab of ego on a plate.

Truth Social: No One’s Speaking the Truth

After Twitter kicked Trump out, he created Truth Social, the platform for “free speech.” Free speech, sure — but at a cost. By mid-2023, Truth Social had burned through $73 million and was about as popular as a root canal. The platform aimed to be the next big thing, but it turned out to be more like Trump Steaks — expensive and underwhelming.

Trump Shuttle: Grounded Before It Took Off

In the late ’80s, Trump decided he could do airlines better than the pros. He launched Trump Shuttle, offering passengers gold-plated fixtures because, you know, that’s what air travelers need. But guess what? Fancy decor doesn’t fix debt. The airline crashed financially and got sold off to USAir in 1992. One more disaster in the Trump portfolio.

Trump Taj Mahal: From “Eighth Wonder” to Bankruptcy

Trump opened the Trump Taj Mahal in Atlantic City, dubbing it the “eighth wonder of the world.” Turns out, it was more like the eighth wonder of how to lose money. Less than a year after opening, the Taj Mahal went bankrupt, like a gold-plated money pit. Oh, and let’s not forget the $10 million fine it racked up for money laundering violations. Wonder no more.

Tour de Trump: Cycling’s Punchline

In 1989, Trump tried to get into cycling with the Tour de Trump, a shameless PR stunt to rival the Tour de France. It was met with protests and mockery, and surprise, surprise — it flopped after two years. Turns out slapping your name on a bike race doesn’t make it successful. Who knew?

The Apprentice: The Lone Success

Somehow, The Apprentice worked. The show painted Trump as a no-nonsense businessman, despite all the evidence to the contrary. It ran for over a decade, propelled him to stardom, and paved the way for his presidency. But even this ended in controversy, with the show’s end coinciding with his political fallout.

Conclusion: A Master of the Mess

Trump’s business career is one long reality show of high-stakes gambles and epic failures. The guy builds, then bankrupts, all while pretending it’s someone else’s fault. From sports teams to steaks, airlines to social media — if there’s a way to crash and burn, Trump’s found it. But hey, at least the man knows how to entertain, right?

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