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These Are Trump’s Biggest Achilles’ Heels: Wolff

January 21, 2026
in News, Politics
These Are Trump’s Biggest Achilles’ Heels: Wolff

Donald Trump may project supreme confidence one year into his second term, but hidden Achilles’ heels are waiting to shatter his “illusion of strength,” his biographer says.

Author Michael Wolff discussed on the Inside Trump’s Head podcast how Trump has relied on a “strongman persona” to bulldoze centuries of norms since his return to the White House.

“He’s a fool, and he may be a madman, and everything that he does is in some profound way counterproductive,” Wolff told co-host Joanna Coles. “Except for the fact that this strongman persona pulls him through.”

US President Donald Trump arrives to take part in a dedication ceremony for Southern Boulevard, in the ballroom at Mar-a-Lago in Palm Beach, Florida, on January 16, 2026. (Photo by ANDREW CABALLERO-REYNOLDS / AFP via Getty Images)
One year into his norm-shattering second term, President Donald Trump is being dogged by at least two “Achilles’ heels,” according to Michael Wolff. Andrew Caballero-Reynolds/Getty Images

Wolff said that Trump’s “persona of dominance” has fueled a “mythology of the man who gets away with everything.”

But he argued that two key vulnerabilities that have emerged—ICE’s increasingly unpopular operation in Minnesota and Trump’s economic shortcomings—could finally trip up the 79-year-old president.

“Minneapolis is an Achilles heel‚” said the author, who wrote his 2018 bestseller Fire and Fury based on his behind-the-scenes observations in the White House.

The public has appeared to sharply turn on Trump’s deportation agenda and ICE as videos of confrontations between Minnesotans and ICE agents have circulated widely—including of the killing of Renee Good.

A new poll from CBS News/YouGov conducted between Jan. 14-16 found that 52 percent of people think ICE is making communities less safe, as opposed to 31 percent who say ICE is making communities more safe.

Most Americans believe that ICE is “too tough” in its tactics (61 percent) and that the agency is not prioritizing dangerous criminals (56 percent).

WASHINGTON, DC - OCTOBER 08: U.S. Secretary of Homeland Security Kristi Noem (R) speaks as U.S. President Donald Trump listens during a roundtable discussion in the State Dining Room of the White House on October 08, 2025 in Washington, DC. Trump’s administration held the roundtable to discuss the anti-fascist Antifa movement after signing an executive order designating it as a “domestic terrorist organization”. (Photo by Anna Moneymaker/Getty Images)
Homeland Security Secretary Kristi Noem called Renee Good a “domestic terrorist” just hours after her killing, while Trump said the mother-of-three was being “disrespectful” to ICE.
Anna Moneymaker/Getty Images

Meanwhile, 54 percent of Americans believe that the shooting of Good, 37, by ICE agent Jonathan Ross, 43, on Jan. 7, was not justified, with 28 percent saying it was justified.

Trump responded to the backlash to the shooting by flooding Minneapolis with more agents and insulting the killed mother-of-three.

Wolff, who said Trump learned to always double down and never retreat as the star of The Apprentice, suggested that the president had ordered the ICE surge as an “effort to distract from” the Jeffrey Epstein files controversy, itself a potential Achilles’ heel for the president.

But “the largest Achilles’ heel,” according to the author, “is the economy.”

While Trump vowed to “vanish” inflation and “make America affordable again,” he has struggled to make good on his promises—something Americans appear to have taken note of.

A Reuters-Ipsos survey conducted Jan. 12-13 found 36 percent of Americans approve of how the billionaire president is handling the economy. A Jan. 8-11 AP-NORC survey found his economic approval rating at 37 percent.

“The promises that Donald Trump made, certainly about bringing down the price of groceries, hasn’t come to pass,” Coles observed. “Groceries are more expensive. People feel the cost of living. Healthcare premiums have gone up.”

As inflation remains unrelentingly high, the labor market also continues to struggle, with unemployment at 4.4 percent across the country.

Trump, however, seems to think his disastrous polling among voters is a matter of messaging.

He threw his own team under the bus on Tuesday, saying, “We’ve had the best stock market in history, the best 401Ks in history. And we inherited a mess. The numbers that we inherited were way up. And now we brought them, almost all of them, way down. I mean, I’m not getting—maybe I have bad public relations people, but we’re not getting it across.”

When reached for comment, White House Deputy Press Secretary Abigail Jackson told the Daily Beast in a statement, “Anything said on the Daily Beast podcast is equivalent to screaming into the void. No one listens to this Trump Derangement Syndrome therapy session.”

The latest episode of the Inside Trump’s Head podcast drew more than 295,000 views on YouTube alone.

Find and subscribe to Inside Trump’s Head with Michael Wolff and Joanna Coles on YouTube and wherever you get your podcasts. New episodes of incomparable insight into the psyche of the world’s most talked-about man drop every Tuesday, Thursday, and Saturday evening on YouTube and Wednesday and Friday mornings on other podcast platforms.

The post These Are Trump’s Biggest Achilles’ Heels: Wolff appeared first on The Daily Beast.

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