Trump’s Iran war is turning out just like his bankruptcies
Trump trusts his gut on big decisions, even though his gut has been wrong many, many times.
Americans knew, or should have known, that Donald Trump’s businesses declared bankruptcy six times when he first ran for president in 2016. Voters didn’t mind then, or in 2024 when they elected Trump to a second term.
But those bankruptcies loom larger now that Trump has bumbled into a Middle East war he can’t figure out how to end. Trump’s decision to attack Iran on February 28 triggered a global energy crisis that has sent the price of oil and other commodities 50% higher and led to dire shortages in some parts of the world.
American bombs have damaged Iran’s military, but Iran has clapped back by shutting down the Strait of Hormuz and throttling Persian Gulf energy supplies. The world now waits to see whether Trump can force the reopening of the strait or Iran will indefinitely enjoy newfound leverage over global energy markets.
Trump’s bankruptcies foretold all of this. Other rash Trump actions, such as his trade wars, revealed poor judgment and a weak grasp of economic fundamentals. But the Iran war scaled those shortcomings up to the level of catastrophic blunder. Here are three prominent similarities between the Iran war and Trump’s six bankruptcies.
Lousy instincts. Trump says he trusts his gut on major decisions, including whether to attack Iran. One can reasonably ask why, given that Trump’s gut instincts have often been terribly wrong.
[See how the economy damage from the Iran war is spreading]
Trump trusted his gut—and ignored expert advice—on many of the decisions that led to the bankruptcies of three Atlantic City casinos in the early 1990s, and New York City’s Plaza Hotel in 1992. One of Trump’s biggest mistakes was overpaying for assets such as the Eastern Airlines shuttle (which he bought in 1988), some of his casino properties, and the Plaza. Trump often eschewed detailed valuation analysis and just bid what he thought was right.
Experts didn’t just point out Trump’s mistakes after the fact, when his businesses failed. They called them out in real time. Trump’s fellow real-estate developers thought he vastly overpaid for the Plaza, which he bought for $407 million in 1988. “Donald’s purchase of the Plaza was greeted with howls of ridicule in the Manhattan real-estate industry,” journalist Harry Hurt III wrote in a 1993 book. Basic revenue projections showed Trump would need to fill every room at the hotel, every day, at rates 250% higher than the prevailing prices, just to make interest payments on the debt he took on to buy the hotel.
Before the Taj Mahal casino even opened in 1990, one prominent analyst correctly predicted that it would fail, because it would require unprecedented amounts of revenue to stay solvent. The Taj was bankrupt a year later.
[See 5 things to know about this year’s midterm elections]
Trump’s gut failed him on Iran because he completely disregarded anything Iran might do in response to a US attack. What makes this oversight especially galling is that there’s extensive analysis at the Pentagon and other government agencies predicting that if attacked, Iran would block the Strait of Hormuz and attack energy infrastructure elsewhere in the Gulf, which is exactly what it did. Trump’s top military advisers told him this, according to media reports. Trump trusted his gut over the experts and the whole world is now paying a steep price.
Glutton for failure. Trump kept trying to make a go of Atlantic City casinos, even as other states began to allow gambling and the Atlantic City casino market was well past its peak. A public company he ran, Trump Hotels & Casino Resorts, went bankrupt in 2004 after nearly a decade of unprofitability. It reorganized and went bankrupt again in 2009. Trump won anyway, because by then, he had learned to charge his own companies fees to use his name and provide other services some analysts considered dubious.
The Iran equivalent is Trump’s repeat insistence that the Iran war will end any minute and everything will soon get back to normal. In early March, during the first week of the war, Trump said, “we expect a very swift conclusion.” He has been spouting similar rosy updates almost daily ever since, as oil and gasoline prices go higher and higher. Reality is not unfolding the way Trump wants it to.
Trump first, the little guy last. Trump is notorious for stiffing contractors while protecting his personal wealth. His Atlantic City bankruptcies left hundreds of local businesses unpaid and thousands of workers furious. One lesson Trump drew from his first four bankruptcies was never to put his personal money at stake, and always rely on creditors and other investors, as he explained to biographer Timothy O’Brien. That would protect his personal fortune if the business went bust.
The little people hurt by Trump’s Iran misadventure are millions of Americans now paying more for gas, food and many other products. Interest rates are up, raising borrowing costs for everybody. Conditions are even worse in Asia and Europe. Trump now says he’s not real worried about anybody’s financial concerns. That fits the profile.
[Trump says to hell with affordability]
Does this tell us anything about how or when the Iran war will end? One of the main takeaways from Trump’s business failures is that he always managed to land on his feet, regardless of how badly others got hurt. Trump’s approval rating is now at the lowest point of either presidential term, with some Trump voters now voicing buyer’s remorse. Many other former Trump supporters know the feeling.
Enjoy a cartoon.
You can order this cartoon ☝️ or others like it, plus merch featuring cartoons, at CartoonStock.com.







The American people are already the "accommodating loser" in this bungled affair.
Wake Up! Wake UP! Wake UP!I just wrote little about how so many people are just not paying any attention to what this ego/ maniac is doing to America.People in America just do not seem to understand how foolish this loser is and, he is doing this with your tax money. WAKE UP!!!!!