War-gamer exposes Trump's fatal miscalculation in Iran

U.S. President Donald Trump speaks to the media on board Air Force One on the way to Miami, Florida, U.S., April 12, 2025. REUTERS/Nathan Howard

President Donald Trump’s surprise war against Iran did not factor in the implications of an important consideration, and a foreign policy expert who “war gamed” this conflict is calling it out.

“Kasie, I've war-gamed the Iran war plan a number of times across multiple administrations,” Brett McGurk, the Special Presidential Envoy for the Global Coalition to Counter the Islamic State of Iraq and the Levant under both President Barack Obama and Trump himself, told CNN’s Kasie Hunt on Monday. “And I think what the administration said earlier — a 4-to-6-week military campaign — was about right. If you're going to degrade Iran's defense industrial base, the missiles, the drones, everything, it takes 4 to 6 weeks.”

Yet there is one variable that did not happen in those war games, and it makes a big difference.

“The one thing that usually did not happen in those war games was that on Day One of the campaign, you took out the entire Iranian leadership,” McGurk told Hunt. “That brought this to a whole new level. And therefore the fact that Iran is turning everything on — I think that's not particularly surprising. But we're only about halfway through from where it was originally planned.”

Earlier in his interview with Hunt, McGurk criticized Trump’s press conferences about the Iran war for their “stream of consciousness” quality and added that Trump is probably trying to buy time to resolve the ongoing crisis over Iran blocking the Strait of Hormuz.

“I think here, this is the president buying some time — calming the economic situation in markets and energy prices — because that buys you time,” McGurk told Hunt. “And that is the one tool the Iranians are playing. It's also buying some time to get forces into place. We still have forces moving as we try, over this five-day period, to see if diplomacy has a chance. I hope it does. I hope an Iranian can come forward and say, ‘I'm speaking now for what's left of our system, and we're prepared to sit down and do a deal.’”

Yet he added, “I'm just — I don't see that happening. So I suspect that by the end of this week, the military campaign is continuing. We're not hitting energy sites, but we're hitting everything else that was on the target list. That will continue through the week, and by the weekend, we might be kind of back to where we started — with Marine Expeditionary Units moving in and other things that give the president a number of options. So I don't see this ending anytime soon, Kasie. I'm just trying to analyze it as best I can in a neutral way.”

Hunt then asked Marc Short, who served as Trump's legislative affairs director from 2017 to 2018, about the president's mindset in approaching this war. He agreed with McGurk's analysis, adding that "he's giving himself five days to see if any negotiations happen."

Trump’s problems do not end with the chaos caused by assassinating Iran’s leadership. Phil Klay, a novelist and Marine Corps veteran from President George W. Bush’s Iraq war, explained in The New York Times earlier this month that the war’s prosecution has been inherently demoralizing.

“I have plenty of complaints about the war I served in two decades ago: the Iraq war was ill-conceived, hubristic and marred by poor leadership at the highest level,” Klay wrote. “But I did know why I was there. What exactly do our service members think we’re trying to do in Iran?”

Denouncing the Trump administration’s “stunningly incoherent” explanations for the war, Klay concluded that “in President Trump’s America, there may be only two genders, but our military adventures can identify however they please.” Noting that they seem to exult in “mixing images of death and destruction with footage from video games or sports highlights,” Klay described the president’s actions as “macho posturing.”

Similar to McGurk and Klay, former U.S. ambassador to Lebanon Jeffrey Feltman and Levant director for the Pentagon Mara Karlin wrote in The New York Times earlier in March that Trump’s “cavalier approach” in Iran is putting Americans and others in danger. In addition to leaving U.S. diplomats and their families on their own to evacuate the Middle East, they also pointed out that America is not accounting for the scale of the Iranian response, which has shut down travel across the region and increases the risk of retaliatory acts of terrorism.

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