President Trump’s longtime biographer, Michael Wolff, has shared details about what happened in a White House Situation Room meeting about Iran. His account is very different from what Trump posted on social media. According to Wolff, the president asked for advice, got frustrated with the answers, and then told a different story online.
Last week, Trump gathered top administration officials in the White House Situation Room to discuss options amid tensions with Tehran. Vice President JD Vance, Secretary of State Marco Rubio, Joint Chiefs of Staff Chairman Gen. Dan “Raizin” Caine, CIA Director John Ratcliffe, and White House Chief of Staff Susie Wiles were all present.
According to The Daily Beast, Trump had been considering launching an initial strike on Iran, with the possibility of a broader military assault later in the year if Tehran did not give up its nuclear program. Reports had also surfaced that Gen. Caine urged caution, highlighting risks such as potential casualties, depleted air defenses, and an overstretched military.
Trump’s public posts about the meeting contradict what his own biographer says actually happened inside the room
According to Wolff, who hosts the Inside Trump’s Head podcast with Joanna Coles, the meeting left Trump frustrated. Relaying a report from someone close to the situation, Wolff described it as a “very typical Trump meeting,” saying Trump “asked for analysis and then didn’t listen.”
Wolff added that Trump “asked for solutions and then was irritated that no one could provide a clear path,” and “demanded assurances of success and got mad at the generals and the experts who flatly couldn’t give him those assurances.”
Those reports about Gen. Caine’s cautious stance apparently prompted Trump to post a rebuttal on social media. Trump wrote, “General Caine, like all of us, would like not to see War but, if a decision is made on going against Iran at a Military level, it is his opinion that it will be something easily won.”
Trump also insisted that Caine “has not spoken of not doing Iran, or even the fake limited strikes that I have been reading about, he only knows one thing, how to WIN.” This is not the first time Trump has faced pushback over his handling of sensitive situations, he recently made headlines after joking about being impeached over a White House invite.
But Wolff’s account contradicts this. “General Caine apparently outlined that there were very problematic tactical and strategic issues here,” Wolff revealed. He added that Trump “translated that into saying, basically, ‘We can do it. Everything is gonna go great. It will be a success.'”
Wolff also said Trump spent time in the meeting pushing for an approach similar to what the U.S. did in Venezuela, where forces seized President Nicolás Maduro and his wife. Experts in the room reportedly pushed back, saying, “Well, this situation is nothing like Venezuela.”
Wolff also noted that Trump has been telling people at the White House, “I have to look strong, not weak,” and “Don’t let them f— me over.” These tensions come amid a broader pattern of Trump’s shifting policies drawing sharp criticism, including from his own Supreme Court picks.White House spokesperson Anna Kelly offered the official position, stating, “President Trump listens to feedback from all members of his national security team, and he is always the final decision maker.”Â
Before Trump’s State of the Union address, Rubio and Ratcliffe also gave an Iran briefing to the bipartisan “Gang of Eight” group of top lawmakers. Senate Minority Leader Chuck Schumer told reporters afterward, “Look, this is serious, and the administration has to make its case to the American people.”
Published: Feb 25, 2026 03:15 pm