Donald Trump’s most well-known critic, Michael Wolff, has accused the Republican candidate of entering a war with Iran without proper preparation or strategic planning.
On the Inside Trump’s Head podcast, Wolff compared Trump’s approach to that of a student who did not prepare for an important exam.
“I think of Donald Trump as just a guy who didn’t do the homework,” Wolff said.
He also added that U.S. presidents normally receive detailed briefing books and constant intelligence updates that inform major decisions, such as launching an operation that could lead to war. The author further claimed that Donald Trump has largely ignored the strategic planning and made decisions in a hurry.
According to Wolff, strategic planning is important. It sets the framework for the war and its objectives. It also prepares leaders for what could go wrong if the initial plans do not work out.
He recalled the president once describing himself as “an ad-lib guy.” This refers to someone who prefers making decisions on the spot rather than relying on detailed planning.
“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.”
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These remarks came after Trump ordered a large-scale military strike against Iran that was planned with Israeli forces on Feb. 28. Under Operation Epic Fury, Iran’s supreme leader, Ayatollah Ali Khamenei, as well as his daughter, son-in-law, and grandson, were killed.
Trump called Khamenei “one of the most evil people in history” as thousands protested in the capital following news of his death.
According to Al Jazeera, Iran’s President Masoud Pezeshkian described the death of the 86-year-old, saying, “This tragic event is the greatest trial facing the Islamic world today.”
As of March 1, 2026, Iran launched retaliatory missiles and drone strikes in response to U.S.- Israel’s joint attacks. These affected several Gulf countries as they rushed to close their airspaces and issue advisory warnings.
Meanwhile, former National Security Advisor John Bolton also addressed similar views on The Daily Beast podcast regarding Donald Trump’s leadership style.
He claimed Trump “didn’t take briefings all that seriously” and would “frequently talk more than the intelligence briefers, which makes it hard to consume intelligence.”
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He further said that Trump appeared uneasy in the White House Situation Room, where major national security decisions are discussed.
According to The Times, officials had spent months discussing military plans against Iran. A Situation Room meeting was then held on February 18.
Vice President JD Vance, Secretary of State Marco Rubio, Central Intelligence Agency (CIA) Director John Ratcliffe, and White House Chief of Staff Susie Wiles, along with Trump and other important members, were busy discussing further military decisions.
During the meeting, Gen. Dan Caine, chairman of the Joint Chiefs of Staff, explained several military options against Iran. One option was a small, limited strike to pressure Iran during talks.
JD Vance, on the other hand, was personally against attacking Iran and also opposed a limited strike. He argued that if the U.S. decided to attack Iran, it should act quickly and with full force rather than a small strike.
Another option was a larger military strike that would overthrow Iran’s government for good. Dan Caine warned that a larger strike would potentially mean higher risks, more American casualties, and the use of more weapons and resources.
Three days later, while en route to an event in Corpus Christi, Texas, Trump gave the final order to begin the operation, stating: “Operation Epic Fury is approved. No aborts. Good luck.”
