Politics

I Know the Real Reason Trump’s War Is in Disarray

GOING IN BLIND

As his war escalates, Trump is “flying by the seat of his pants” because he refuses to do his homework, according to his biographer.

Donald Trump plunged the country into war with the preparation of a student who skipped the syllabus, his biographer says.

“I think of Donald Trump as just a guy who just didn’t do the homework,” author Michael Wolff said of the notoriously reading-averse president on the Inside Trump’s Head podcast.

“Imagine in a normal world, you’re going to war, one of the things that you get if you’re the president of the United States—the commander-in-chief—is briefing books, constantly,” Wolff said.

U.S. President Donald Trump salutes as members of military carry a transfer case during a dignified transfer of the remains of six U.S. Army service members of the 103rd Sustainment Command, who were killed in Kuwait, Major Jeffrey O'Brien, Capitain Cody Khork, Chief Warrant Officer 3 Robert Marzan, Sergeant 1st Class Nicole Amor, Sergeant 1st Class Noah Tietjens and Sergeant Declan Coady, amid the U.S.-Israeli conflict with Iran, at Dover Air Force Base in Dover, Delaware, U.S., March 7, 2026. REUTERS/Kevin Lamarque
Trump’s former national security advisor John Bolton told ‘The Daily Beast Podcast’ last week that the president often “didn’t care about” or simply “couldn’t process” briefings. Kevin Lamarque/Kevin Lamarque/REUTERS

The author argued that briefings are crucial for presidents to map out a potential war’s objectives, its implications, and the scenarios that could play out.

But Trump, 79, has done “none of that” and is “flying by the seat of his pants,” according to Wolff.

“He’s a vacancy in the middle of his own world, and yet a vacancy that is fully in charge,” Wolff told co-host Joanna Coles. “The situation could not be more dire.”

Trump, not known for being well-read, has sought to keep his school records private, according to his former attorney Michael Cohen, who said Trump ordered him to write to Fordham University before the 2016 election to demand that his transcripts remain secret.

The president’s niece, Mary Trump, has alleged that Trump paid “a smart kid” to take his SATs to help him transfer from Fordham University in the Bronx to the undergrad Wharton business school at the University of Pennsylvania.

Trump’s former national security adviser, John Bolton, told The Daily Beast Podcast last week that the president often “didn’t care about” or simply “couldn’t process” the briefings his advisers prepared.

Bolton said Trump “didn’t take briefings all that seriously” and would “frequently talk more than the intelligence briefers, which makes it hard to consume intelligence.”

John Bolton listens as President Donald Trump in the Oval Office at the White House on July 18th, 2019 in Washington, DC.
“He’s the only president I’ve seen who felt uncomfortable in the Situation Room,” John Bolton said of Trump. Jabin Botsford/The Washington Post via Getty Images

Despite having long called for regime change in Iran, Bolton said he was “very worried” that Trump “hasn’t thought through the implications or laid the groundwork” of his ambitions in the escalating conflict, which has already claimed the lives of seven U.S. troops and more than 1,000 civilians, according to reports.

It has become clearer by the day that Trump launched his strikes against Iran on Feb. 27 without a coherent plan for the war or a clear endgame—something reflected in his constant contradictions and those of his own aides.

Defense Secretary Pete Hegseth said that the administration is not waging “a so-called regime change war” and is instead aiming to curb Iran’s nuclear program. But Trump has called on the Iranian people to topple the Islamic regime and demanded that he be involved in choosing its next leader after Iran’s Supreme Leader Ali Khamenei was killed.

The regime defied Trump, choosing Khamenei’s 56-year-old son Mojtaba Khamenei, a hardliner, as the new supreme leader.

On Friday, Trump appeared to abandon his historic contempt for America’s “forever wars” when he said he would keep the war going until Iran’s “UNCONDITIONAL SURRENDER.”

But after oil prices skyrocketed, he said Monday, “I think the war is very complete, pretty much.”

On Tuesday, Hegseth announced, “Today will be, yet again, our most intense day of strikes inside Iran.”

Wolff, who was granted access to the White House during Trump’s first term, said the commander-in-chief is “ad-libbing” the war.

“I’ve heard him say this to me: ‘I’m an ad-lib guy,’” Wolff said. “That’s how he sees this. He’s on stage and he’s making it up as he goes along and very proud of that ability.”

When reached for comment, White House Communications Director Steven Cheung provided the Daily Beast with a recycled statement.

“Michael Wolff is a lying sack of s--- and has been proven to be a fraud. He routinely fabricates stories originating from his sick and warped imagination, only possible because he has a severe and debilitating case of Trump Derangement Syndrome that has rotted his peanut-sized brain,” Cheung said.

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.