Michael Wolff, the author and longtime chronicler of Donald Trump, told the Inside Trump’s Head podcast that the president pushed the United States into a conflict without the routine preparation usually provided to a commander-in-chief. Wolff likened Trump to a student who "didn't do the homework," arguing that the administration lacked the briefing structure presidents typically use to define objectives, weigh consequences and plan scenarios.
"I think of Donald Trump as just a guy who just didn’t do the homework," Wolff told co-host Joanna Coles. "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 — briefing books, constantly." He added, "He’s a vacancy in the middle of his own world, and yet a vacancy that is fully in charge."
"He’s flying by the seat of his pants," Wolff said, warning that "the situation could not be more dire."
Wolff and other former officials said Trump has frequently avoided or struggled to engage with detailed written briefings. John Bolton, Trump’s former national security adviser, told The Daily Beast podcast that the president often "didn’t care about" or appeared unable to process the briefings his aides prepared, adding that Trump "didn’t take briefings all that seriously" and would sometimes dominate discussions in ways that made it hard for intelligence to be absorbed.
Critics say that approach contributed to an unclear strategy after U.S. strikes against Iran on Feb. 27. Reports indicate the conflict has so far resulted in the deaths of seven U.S. service members and more than 1,000 civilians, though casualty figures are still being confirmed by multiple sources. Observers have pointed to conflicting public statements from the president and administration officials as evidence of a lack of coherent objectives and an undefined endgame.
“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
For example, Defense Secretary Pete Hegseth has emphasized that the administration is not pursuing a "so-called regime change war" and is focused on curbing Iran’s nuclear capabilities. At the same time, President Trump publicly urged Iranians to rise up against their government and reportedly suggested he wanted a role in shaping Iran’s post-Khamenei leadership after reports that Supreme Leader Ali Khamenei had been killed — an account that was contradicted when the regime reportedly named Mojtaba Khamenei as successor.
Wolff, who had White House access during Trump’s first term, said the president has described himself as an "ad-lib" leader. "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."
The biographer also referenced long-standing reports about Trump’s reluctance to disclose academic records: Michael Cohen, a former attorney, said he was asked to contact Fordham University to keep Trump’s transcripts private, and Trump’s niece Mary Trump has alleged that Trump paid someone to take his SATs to facilitate a transfer to Wharton — allegations Trump has denied.
When asked for comment, White House Communications Director Steven Cheung issued a strongly worded statement calling Wolff "a lying sack of s---" and accusing him of fabricating stories. The White House later characterized the response as a recycled statement.
Observers and former officials say the combination of improvisation at the top, mixed messaging from senior aides and the absence of a clear declared strategy has left the U.S. approach to the conflict appearing disjointed and unpredictable. Analysts say clarity on objectives, political and military planning, and post-conflict contingencies remain essential to avoid further escalation.
