Donald Trump: The World’s Worst “Successful” Businessman

Posted on March 4, 2025

For decades, Donald Trump has insisted he is a brilliant businessman, a titan of industry, and the very embodiment of the American Dream. But let’s take a moment to pop that gold-plated, ego-inflated bubble. The reality? He’s less a self-made billionaire and more a rich kid with a knack for setting piles of money on fire while convincing people he’s a financial genius.

The Bullshit Empire Trump Didn’t Build

Trump likes to tell the story of how he built his empire from “a small loan of a million dollars” from his father, Fred Trump. That nice. In reality, The New York Times reported in 2018 that Trump received at least $413 million in today’s dollars from his father’s real estate empire, much of it through tax dodges that would make even the most creative offshore accountant blush.

Trump didn’t inherit just money; he inherited an entire successful business. His dad was a legitimate real estate mogul in New York, focused on middle-class housing. Instead of coasting on that success, Donald decided to rebrand himself as a high-rolling dealmaker. The results? A staggering, almost artistic level of financial failure.

The Art of the (Terrible) Deal

Trump’s business record reads like a cautionary tale of what happens when you mix arrogance with financial illiteracy. Here are some of his greatest hits:

Trump Casinos: You know you are shit at business when you can’t make money in a casino. Trump managed to bankrupt not one, not two, but three casinos, including the Trump Taj Mahal in Atlantic City. Casinos are essentially money vacuums that take cash from drunk tourists, yet Trump still found a way to go bust. What a businessman!

Trump Airlines: In 1988, he bought a fleet of planes, slapped his name on them, and acted like he was the next Howard Hughes. The airline lasted about three years before collapsing under crushing debt. Turns out, branding a shuttle service for business travellers with gold fixtures was not a stroke of genius.

Trump University: A “school” that promised to teach people Trump’s business secrets but turned out to be a glorified fraud. In 2016, Trump had to cough up $25 million to settle fraud lawsuits. That’s right—the man who claims to have all the answers in business literally had to pay millions because his own “university” was deemed fraudulent. Fuck me.

• Trump Steaks, Trump Vodka, Trump Water: A bizarre collection of overpriced, failed vanity products. Nothing promotes “high-quality beef” like an overweight oaf who eats his steak well-done covered in ketchup.

Trump. More Toddler Than Titan.

For someone who claims to be a business genius, Trump has a truly fascinating habit of losing money at an astonishing rate. A 2019 report by The New York Times found that between 1985 and 1994, Trump lost more money than almost any other American taxpayer. That’s right he wasn’t just bad at business, he was historically bad.

Even as president last time round, he seemed more interested in suing people on Twitter than running a functioning government. Instead of a savvy CEO, this time round he is acting more like a toddler denied his favourite toys, except in this case, the toy is America’s democracy.

A Clown with a Trust Fund

Trump’s business career isn’t a story of brilliance it’s a masterclass in bullshit branding over substance. He took his father’s fortune, blew much of it on bad deals, failed businesses, and lawsuits, and somehow convinced millions of people that he’s the king of capitalism. Mugs.

If Trump is a great businessman, then the Titanic was a great success because it floated for a little while. What is the real art of the deal? Convincing people you’re successful, even when the numbers say otherwise.

Seems that way.


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