The Democratic surge in the midterm elections is a huge surprise that seemed unthinkable just a few months ago. Yet it fits the pattern of failure Donald Trump exemplified in his raucous career as a developer and casino operator, before he pivoted to reality TV and its cousin, national politics.
Trump’s businesses declared bankruptcy six times between 1991 and 2009. The details were thoroughly reported when Trump ran for president the first time, in 2016. Voters didn’t seem to mind, and some believed Trump was the self-mythologizing business guru he portrayed on “The Apprentice.”
Yet the core mistakes that made Trump a serial bankrupt have attended both of his presidential terms. And now they’re bringing down the Republican Party just as they brought down Trump Taj Mahal, Trump Plaza, Trump Hotels and Casinos, Trump Entertainment Resorts, and the others. And the GOP may have further to fall. The 2026 wipeout could lead to the loss of the White House in 2028 and a period of exile in which the party can’t win with Trump but can’t shake him, either.
Here’s how Trump wrecked his businesses much as he is wrecking the GOP.
Horrible instincts. Trump famously trusts his gut. He shouldn’t. He did this many times as a developer, while ignoring expert advice, and it constantly got him into trouble. In the 1980s and 1990s, Trump was famous for overpaying for assets such as the Eastern Airlines shuttle, several casino properties, and the Plaza Hotel. Trump often rejected detailed valuation analysis and just bid what he thought was right. Then he went insolvent as revenue failed to cover the excessive debt payments he took on to finance deals bound to fail.
[What Democrats need now: A convincing leader]
Trump demonstrated the same lousy judgment when he started the Iran war in February and triggered a global energy crisis voters just punished him for. Other pet projects, such as imposing tariffs and hounding migrants, have blown up in his face as well. Experts could have told him this would happen, but he knew better. Trump also endorsed horrible Republican candidates such as Ken Paxton in Texas, helping them win primary elections even though they had poor general election prospects. Trump’s judgment is so bad that it doesn’t even seem like he wants to win because he sabotages himself in plain sight.
Always other people’s money. Trump generally lived to fight another day after each of his bankruptcies because most of the money he lost belonged to others. That’s why he often described himself as the “king of debt.” Debt is borrowed money, and Trump excelled at risking whatever he could borrow. Elon Musk, who spent $474 million trying to save the Republican Party from Trump, and other tech billionaires who funded the Republican midterm effort, were the 2026 equivalent of the banks that lent Trump millions for his business fantasies and ended up with pennies on the dollar.
Trump first, organization last. Trump has used the presidency for personal gain more than any president in modern history, and probably ever. The GOP is the vehicle he used to do it. Trump will end his second presidency billions of dollars richer. The party, by contrast, could take years to recover, the equivalent of a broke company reduced to selling off core assets.
It always takes willing dupes. Trump does have a huckster’s ability to sell his vision and lure others into partnerships that can’t possibly end well. He was still able to find banks willing to lend him money after his second, third, and fourth bankruptcies. One of those companies even went public in 1995, with millions of individuals buying stock proffered by a failed businessman. Today’s Republican Party is filled with Trump enablers who sing his praises, mimic his taglines, and fight his battles, and will still get left cleaning up when Trump has milked everything he can from them.
[The Trump economic bust, in 10 charts]
If you’re a Trump competitor—which the Democratic Party assuredly is—you glory in the foibles of your adversary. Democrats have made a huge market share grab in 2026 and could seize even more ground in 2028. But Americans need two healthy parties able to craft pragmatic solutions to serious problems, and half of the market is currently in disarray. The Republican Party deserves it, but American voters do not.
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Excellent parallels - very insightful!