Why Trump’s Biggest Weakness Is About to Doom Him: Author

Photo Illustration by Victoria Sunday/The Daily Beast/Getty Images President Donald Trump is crippled by a political Achilles’ heel that transcends America’s partisan trenches, according to his biographer.

“Donald Trump... has screwed himself, which he does over and over and over again,” Michael Wolff told the Inside Trump’s Head podcast.

The author described Trump’s return to the White House after his political comeback in 2024 as a headlong rush driven by his belief that he could do whatever he wanted and would do it as fast as possible, without anyone being able to stop him.

“Which he did,” Wolff said, “but the problem with all that is that that means nothing is particularly thought out.” Now, with roughly seven weeks until the midterms, that means “it’s hard to see how he... benefits from anything he has done, from the war, to the economy, to healthcare, to immigration,” he argued.

But Trump’s biggest liability is the economic squeeze bearing down on Americans every day, an issue he promised to “end” but has instead made worse, Wolff said.

The Trump biographer explained that the president can’t escape the fallout from high prices because the issue “cuts across” political divides.

“There’s no ideology attached to that, no partisanship,” he said.

“It’s just things are... way more expensive than people believe they ought to be... and when that happens you look for someone to blame; there’s one logical person to blame... and that’s the president of the United States.” He pointed to how much inflation has reshaped the price of everyday goods: Beef prices have risen 96 percent since 2012, while bread is up 46 percent and new-car prices 25 percent, according to a New York Times analysis of Bureau of Labor Statistics data .

“It is not just Donald Trump,” Wolff said, “but... the buck stops here because he is the president.” Overall inflation remained elevated at 3.4 percent in August, up from 3 percent when Trump returned to the White House in January 2025.

Wolff noted that the 80-year-old president has played a major part in fanning inflation since returning to office, with his trade wars and the war with Iran both adding to price pressures.

“This is of his own making.

The war is of his own making; tariffs are of his own making.

They are the kinds of things that contribute to raising prices,” Wolff said.

Trump has thereby stepped into another political bind: interest rates.