U.S. President Donald Trump speaks as he meets with German Chancellor Friedrich Merz (not pictured) in the Oval Office at the White House in Washington, D.C., U.S., March 3, 2026. REUTERS/Jonathan Ernst
President Donald Trump seems to be "counting on" one of his oldest tricks to "win" his new war in Iran, according to one of his biographers.
Throughout his career, Trump has sought to portray himself as a fighter who wins whatever battle he enters, journalist Michael Wolff, who has written four books about Trump, argued in a new op-ed for The Daily Beast on Monday. Trump appears to be trying the same thing in Iran, but doing so could be costly, Wolff continued.
"The thesis here, to Trump, was that foreign policy should be what he wanted it to be (people should listen to him, not he to them); it should concentrate on big stuff (results!) and that, whatever we do, we should get something for it; and, most of all, we should always win," Wolff wrote.
"He has unilaterally replaced the long-standing foreign policy establishment with a visceral show of his and America’s dominance—pronouncements, threats, and constant musings about what he might or might not do," he continued. "And, most importantly, 'the win.' The idea that we had fought wars that we hadn’t won actually confounds him."
On Saturday morning, U.S. and Israeli forces coordinated attacks on more than 100 sites across Iran, which included a bombing operation that killed Ayatollah Ali Khamenei and several top military and political leaders in the country. Reports indicate six U.S. military members have died as a result of the campaign.
Since then, the Trump administration has given multiple reasons for the strikes, including allegations that Iran would have attacked the U.S. if another country like Israel attacked them first. Lawmakers on both sides of the aisle have criticized the administration's justifications, arguing that they don't rise to the level of an "imminent threat" required for the operation.
Wolff argued that the shifting stories point to Trump's desire to tell the public that his administration won something in Iran so he can move on.
"He’s counting on being able to sell quick, beautiful victories," Wolff wrote.