Back in late February, President Donald Trump joined Israel in launching strikes on Iran, including an initial strike that killed Iran’s Supreme Leader Ali Khamenei, killing him and other top leaders.
That decision, for which Trump never quite made the case to the American people, came just weeks after the U.S. intervention in Venezuela, which included the arrest of that country’s leader, Nicolas Maduro, and the installation of a pro-Western regime. So the success of that intervention likely emboldened Trump to once again attack Iran.
President Donald Trump greets President Volodymyr Zelenskyy of Ukraine, Friday, February 28, 2025, in the West Wing Lobby. (Official White House Photo by Daniel Torok)
President Donald Trump greets President Volodymyr Zelenskyy of Ukraine, Friday, February 28, 2025, in the West Wing Lobby. (Official White House Photo by Daniel Torok)
It’s fair to say that this time, it hasn’t gone nearly as smoothly.
After a nearly month-long pause, the war continues, and it has remained unpopular, leaving Trump with no good options for reopening the Strait of Hormuz.
This continuing stalemate has contradicted a pair of longstanding Trump promises. He has vowed to reduce inflation and, specifically, keep gas prices down.
And he has claimed over the years that he would keep the United States out of open-ended foreign wars, especially in the Middle East, while claiming his different political opponents would launch such wars.
The New Yorker, in a new analysis published Friday, has looked at why Iran has gone so poorly: Namely, Trump seems to be winging it.
Trump’s “Ad-Lib Strategy”
Robin Wright writes for the New Yorker that Trump has been claiming, for the entirety of the war, that it’s about to be over.
Trump, since the war’s start, “has claimed more than thirty times that Operation Epic Fury has been successful, is over, or almost is, anyway.
None of these pronouncements has panned out; some have bordered on delusional. As the war nears the five-month mark, the latest ceasefire, agreed to in June, has functionally collapsed,” Wright says of the president.
Now, the war is back on, with the U.S. blockading the Strait of Hormuz, while Iran is attacking U.S. interests and allies throughout the Middle East.
Three Different Phases
Richard Haass, in a Substack post this week, pointed out that Trump has changed his strategy repeatedly throughout the war.
“I would argue that as the United States has already tried three strategies in its war with Iran and come up short each and every time, the question is whether Trump has a Plan D. But who’s counting?
The pertinent question is, ” What now?” Haass writes.
He started calling for regime change before pivoting to what he calls “intense bombardment meant to force Iran to capitulate and unconditionally accept U.S. and Israeli terms for war termination.”
That, too, did not work, which was followed by a counter-blockade of the Strait of Hormuz. This phase ended with the “Memorandum of Understanding” in mid-June, but now that, too, has given way to a resumption of hostilities.
Washington is Worried
In Washington, Wright notes in The New Yorker that experts are confused.
“There is a growing sense of despair among foreign-policy experts and former policymakers about the direction of the war—and whether an end to it is even achievable, at least anytime soon, short of diplomatic surrender by either side,” Wright says.
Trump has, depending on the day and the phase of negotiations, said radically different things about his Iranian counterparts, sometimes calling them trustworthy and other times the opposite.
Trump, of late, has taken to calling the Iranians “scum,” “cuckoo,” “sick,” “vicious, violent people,” and “a bunch of lying guys.”
“It is impossible to overstate how quickly and comprehensively the U.S. has undermined deterrence and squandered its leverage over Iran,” Philip Gordon, a former official in Democratic administrations who now works for the Brookings Institution, told The New Yorker.
“It was only Trump’s decision to roll the dice on regime change that led a cornered regime to start attacking its neighbors and close the Strait, grabbing a stranglehold on the world economy,” Gordon said. That genie can never be put back in the bottle.”
David Axelrod, a former Obama political adviser, had a memorable quote about Trump.
“There are days when I feel like an American, like a passenger in a plane being piloted by a 6-year-old. You’re strapped in your seat as the plane dives and weaves crazily, and all you can do is hope and pray that it lands safely.”
About the Author: Stephen Silver
Stephen Silver is an award-winning journalist, essayist, and film critic, and contributor to the Philadelphia Inquirer, the Jewish Telegraphic Agency, Broad Street Review, and Splice Today. Stephen, the co-founder of the Philadelphia Film Critics Circle, lives in suburban Philadelphia with his wife and two sons. For over a decade, Stephen has authored thousands of articles that focus on politics, national security, technology, and the economy. Follow him on X (formerly Twitter) at @StephenSilver and subscribe to his Substack newsletter.
