So You Want To Negotiate With Iran ...

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.

Another essential question: What aspects of Obama’s nuclear deal with Iran is the Trump team willing to learn — or steal — from? 

It might help some Trump administration officials to read the 2015 agreement, otherwise known as the Joint Comprehensive Plan of Action. In fact, here is a link.

They don’t have to like the JCPOA; I’m pretty sure a requirement of being a Trump appointee is that you don’t like it. But it’s worth examining it to understand the level of detail involved in such talks and some of the mechanisms that could prove useful in a future agreement.

There are, for instance, more than 100 references just to the International Atomic Energy Agency in its 159-page text. That agency is crucial to verifying whether Iran is meeting its nuclear commitments, said Daryl Kimball, executive director of the Arms Control Association, which advocates for diplomatic solutions on hot-button topics such as nuclear nonproliferation.

Kimball added that it might help for supporters of diplomacy to stop comparing everything Trump does to the JCPOA, which was crafted under very different conditions. (Trump also tends to disdain anything related to Obama and would not care for comparisons.)

“What Trump needs to think about as he seeks a negotiated outcome is not how his deal might compare with Obama’s, but what does it take today, under different conditions, to block Iran’s potential pathways to the bomb?” Kimball said.

On the outcome front, is there a way to achieve U.S. objectives diplomatically without a single comprehensive peace deal?

It took around two years to pull together the JCPOA, but before it were many years of talks, sanctions and other engagement that included an interim agreement known as the Joint Plan of Action, or JPOA. This temporary deal included some concessions on both sides, but it bought time to negotiate the bigger deal.

The Trump administration may want to pursue a similar interim step. Reaching a diplomatic truce of this kind quickly also could help satiate the president’s appetite for an accomplishment to point to ahead of this year’s midterm elections.

The administration also could skirt the notion of a comprehensive deal and enter talks on multiple tracks, such as about the strait and the ballistic missiles. During the Obama-era nuclear talks, the U.S. held a separate successful track of discussions that freed several Americans held prisoner in Iran.

Finally, what sort of concessions is Trump willing to make to Iran?

Iran is unlikely to agree to much of anything without the U.S. offering some concessions of its own. That includes lifting many of the sanctions the U.S. has imposed on Iran — penalties that have severely limited its ability to conduct business beyond its borders. Iran may even demand that the U.S. formalize the agreement as a treaty, a politically challenging effort in Washington, but one which reduces the odds that Trump or another president could back out of the deal in the future.

I am not sure how else to say this, but this is extremely hard stuff. (Just consider the Iran “snapback mechanism” at the United Nations.) The administration will need the expertise of career government experts, no matter how much it dislikes them.

Iranian officials are many things, but they are not stupid. They care about being treated with respect, even when they are militarily and economically vulnerable. They will not give up something for nothing.

Trump “has to be cognizant of the fact that, without respect and without the willingness to come to a win-win deal, there is just never going to be a deal, regardless of the degree of pressure,” said Ali Vaez, a senior analyst with the International Crisis Group who is in touch with all sides of the U.S.-Iran negotiations.

Even if the Trump administration manages to answer all these questions for itself, it could face problems if it doesn’t consult other geopolitical players, some of whom are no doubt whispering in Iran’s ear.

I don’t see the administration changing its “go-it-alone” style on negotiations. But if it doesn’t at least talk to other countries — including Russia and China — it could find itself at a disadvantage when it needs their help. As just one example: If Iran agrees to hand over its highly enriched uranium, Russia might be the only serious option to take it.

The administration could face other difficulties if it doesn’t loop in Congress. I understand that sounds about as much fun as walking on glass, but Congress has a legal right to review any nuclear deal with Iran and many U.S. sanctions on Tehran are enshrined in law.

In any talks with Iran, the Trump administration also needs to be prepared to walk away, even in the final stages of months and months of negotiations, which is when Iran sometimes likes to make new demands.

If that happens, though, the Trump administration needs to have a plan for what to do next.