6 bankruptcies later, Donald Trump insists he’s the ‘greatest’ businessman America has ‘ever’ had

Donald Trump who has filed for bankruptcy six times, turned a family fortune into a financial rollercoaster, and has a history of bold moves that often end in chaos, is now lecturing America’s business elite on tariffs and their supposed lack of business acumen.

Over the weekend, Trump took to his favorite megaphone, Truth Social, to shout at the country’s top folks: “THE BUSINESSMEN WHO CRITICIZE TARIFFS ARE BAD AT BUSINESS, BUT REALLY BAD AT POLITICS.” (Yes, of course, in all caps. Because why whisper when you can scream?)

Ah yes, Mr. Six-Time Bankruptcy is here to lecture actual businesspeople—who correctly understand that tariffs will crush their businesses and raise prices for consumers—that they are the ones bad at business. pic.twitter.com/xPGtDMjmTw

— Republicans against Trump (@RpsAgainstTrump) April 20, 2025

For a man who loves to brand himself as a financial genius, Trump’s track record tells a different story. His bankruptcies include high-profile flameouts like the Trump Taj Mahal Casino in Atlantic City, which closed its gaudy doors in 1991 after hemorrhaging money. There’s also Trump Plaza and Trump Castle, both of which folded under the weight of bad management and crushing debt. And let’s not forget Trump Hotels & Casino Resorts, which filed for bankruptcy in 2004, leaving investors in the lurch while Trump walked away with his name still intact. Now, to be fair, bankruptcy isn’t always the end of the world in the business world. It’s often used as a strategic reset, a way to cut losses and start fresh. But six times?

That’s a pattern. And while Trump loves to tell you that he was simply playing the system, the system doesn’t look so forgiving to the countless employees, contractors, and investors who got burned along the way. For someone who claims to be a master of the deal, his deals often seem to end with everyone else holding the bag.

Trump’s renewed enthusiasm for tariffs has sent financial markets into a tizzy. The Dow Jones Industrial Average has been performing its best impression of a yo-yo, including a heart-stopping 1,000-point plunge after one tariff announcement. Economic experts—you know, those pesky folks who rely on “data” and “analysis” rather than gut feelings—project automobile price increases of $4,000 to $10,000 thanks to tariffs on parts and materials. The average effective tariff rate is expected to soar to 11.3%, reaching heights not seen since 1943, when the country was mobilizing for a world war, not a trade war. Let’s not forget Trump’s little stunt of pausing tariffs for 90 days

So, is Donald Trump the “greatest friend that American capitalism has ever had”? Not by a long shot. But he might just be its greatest showman. At some point, the greatest con of all might be convincing America that he’s anything more than a salesman with a knack for staying in the spotlight.