Nahal Toosi writes:

President Donald Trump recently dismissed claims he’s anxious to end the Iran war, insisting on Truth Social that he’s “possibly the least pressured person ever to be in this position” and has “all the time in the World.”

If only.

Trump and his aides could use some more time to think through what they want to accomplish in discussions with Tehran’s Islamist regime. The administration’s preparations for launching the war were … not great, and its negotiating efforts so far have underwhelmed. Ending the war — and keeping it ended — is almost certain to prove more complicated than Trump aides suspect.

The administration has a number of fundamental questions to sort through, people who have dealt with Tehran in the past tell me. That won’t be easy given the president’s rhetorical waffling.

“The details are incredibly important,” said Michael Singh, a former George W. Bush administration official who dealt with the Middle East. “Each new administration has to learn those details the hard way. The Iranians on other hand are often the same or similar teams who have negotiated these terms with multiple American administrations. You may receive what you think is a concession by the Iranians, but when you delve into it, it’s a concession from you to Iran.”

I’m still not convinced Trump is ready to genuinely commit to diplomacy with Iran, despite the ongoing ceasefire. He loves using military force and knows that Iran remains the weaker side, even as both the U.S. and Iran wrestle over the fate of the Strait of Hormuz. But at some point, the global economic fallout that is hurting both Americans’ wallets and the country’s reputation may force Trump to the negotiating table.

If he decides to take a serious shot at talks to end the war, the first critical question Trump needs to answer is: Is he prepared to agree to a deal that ultimately leaves the Islamist regime in place?

This is anathema to many Iranians who want an end to a regime that has long brutalized them. It could be intolerable for Israel and some Arab states who view Tehran as the root of many Middle East ills.

Despite Trump’s occasional specious claims that he’s already changed the regime, it’s clear the U.S.-Israel military attacks have failed to dislodge the Islamist system. Iranian citizens didn’t stage an uprising amid the bombing. And given Iran’s demonstrated willingness to seize control of the strait, what’s left of the regime is not without leverage.

The administration may have to decide that a deal is worth more than trying to change who runs Iran and how they do it. If so, it needs to be ready for Iran hawks to undermine its efforts — or at least try to shape them — at every step.

The Israelis, and probably a few Arab countries, too, will use strategic (and often out-of-context) leaks to the media. Think tanks in Washington will churn out arguments for why the U.S. should be tougher, even if it means no deal. The fights on X will get more personal. We’ve all gone through this before, especially around Barack Obama’s nuclear deal with Iran. But now there’s artificial intelligence and Iranian Lego videos!

The bottom line is that many Iran hawks will never trust any deal with this regime because they see the regime’s existence as the problem.

Another major question for the Trump administration to ask and answer: What is the minimum that it will demand of Iran?

Will Trump accept an agreement that covers Iran’s nuclear ambitions but not its ballistic missile program or its support for proxy militias in the region? What about the future of the strait? Every topic left out will be a headache later, but every topic included will make a deal harder to reach. Still, knowing the exact objective is crucial.

Let me be super clear here, especially for certain U.S. envoys who love PowerPoint: A framework is not a deal. A list of however-many points — Iran will do this, the U.S. will do that — with no details such as how, when, where will not be enough to resolve this conflict. That’s especially the case when it comes to figuring out how the U.S. will verify that Iran is keeping its end of the bargain.

The White House says it’s not concerned about the tricky terrain ahead for the president.

“The president has more experience with dealmaking than anyone, and Americans can rest assured that any agreement will put our national security interests first,” spokesperson Anna Kelly told me. [Continue reading…]