U.S. President Donald Trump speaks to reporters mid-flight in the press cabin of the new, Qatari-gifted Air Force One after changing planes to return to Washington from RAF Mildenhall, Britain, July 8, 2026.
New York Magazine writer Jonah Shepp says President Donald Trump considers himself very intelligent — but that intelligence apparently didn’t extend to the definition of “quagmire.”
The U.S. and Iran are back at war again, less than a month after agreeing to a cease-fire deal and Trump’s frustration is visible.
“This is a very unpopular war that Trump reportedly thought would be over in days, then claimed would be over in four to six weeks, then insisted was actually over and fully won when anyone could tell that it wasn’t,” said Shepp. “Five months later, amid an alarming escalation, there’s still no end in sight. From everything Trump has said over the past few weeks, he’s apparently still under the impression that the war is under his control, the U.S. is winning and Iran is overwhelmed and desperate to negotiate, and the costs are not only bearable for Americans, but negligible.”
Worse, Trump’s original war goals, from the threat of a nuclear Iran to the Israeli regime-change scheme he bought into have come and gone, replaced by … nobody’s really sure. These days it’s about the state of the Strait of Hormuz—which Trump himself caused by unilaterally committing war on Iran.
“Welcome to a forever war, in other words,” said Shepp.
Trump dragged Iran and his own voters into war with “unclear, unrealistic objectives, lacking both an articulate theory of victory and an exit strategy,” said Shepp.
Projecting strength and avoiding the humiliation of defeat is tantamount to a guy like Trump, but the war’s unpopularity at home and abroad is putting the heat on Trump to cut and run—as if that would be possible without admitting defeat. Still, escalation doesn’t appear to be getting anywhere except in voters’ wallets.
“Passing over whether Trump is or is not the world-historic genius he perceives himself to be, he has yet to demonstrate a brilliant new strategy to prevent the Iran war from turning into an extended debacle,” said Shepp. “On the contrary, he disdains expertise and has put negotiations with Iran in the hands of two complete amateurs whom their Iranian counterparts don’t trust and whose only accomplishment so far has been a crappy deal for the U.S. that fell apart in weeks. Meanwhile, our armed forces are currently under the direction of a right-wing television personality and televangelist whose latest manosphere-inspired innovation is a policy to test U.S. soldiers for low testosterone.”
Worse, Shepp said that the U.S. diplomatic corps “has been hollowed out and politicized, Iran experts have been lost to budget cuts and ideological purges, and at this rate, Marco Rubio may soon be the only person left working at the State Department.”
“As Trump is now discovering, the U.S. didn’t get bogged down in past wars because his predecessors were ‘dumb,’ but rather because they suffered from historical, political, and ideological blind spots,” said Shepp.