WASHINGTON—As US President Donald Trump inches closer to a potential deal with Iran, a bitter truth has emerged, one plain to anyone who has sat across from Iranian negotiators (or in a room down the hall): Getting Iran to the table is relatively easy. Making a deal is harder. Implementing a deal is all that really matters.
We learned this firsthand through flights halfway around the world, Iran’s maddening insistence on negotiating through intermediaries, and the endless, grinding waiting. These experiences—which the Trump administration is all too familiar with—also helped produce the 2023 deal to secure the release of wrongfully detained Americans from Iran.
Abram Paley holds a rare distinction: he is the last American official to sign a deal with Iran. That agreement secured the release of five Americans in exchange for the commutation of the sentences for five Iranians held in US prisons and the transfer of frozen Iranian assets from South Korea to restricted accounts in Qatar. Those assets remain frozen, at least for now. Nate Swanson was in the White House the day the hostage deal was implemented, serving in the National Security Council (NSC).
As friends and former colleagues, we have had a running exchange of calls, texts, and emails over the past few weeks revisiting our own experiences, the lessons we drew from them, and what matters in the current moment. What follows is an abridged version of that conversation.
Nate: The 2023 Iran hostage deal was a foundational experience for both of us. I was at the NSC as the director for Iran. You had recently taken over as the acting special envoy for Iran and lead negotiator/implementer on this effort. The terms for the deal were largely finalized prior to your arrival, and both sides wanted to get the deal done as quickly as possible. Yet this deal took a long time to materialize. Why?
Abram: The context is almost as important as the deal itself. The outlines of the 2023 hostage deal were broadly in place well before we stepped into our roles. But despite best efforts to free these Americans as quickly as possible, the deal did not come together. I’d say a key role we both played was identifying the opportunity to close the deal.
Nate: Right. In 2021, the Biden administration initially assumed returning to the 2015 Joint Comprehensive Plan of Action (JCPOA) might be easier than a hostage deal and insisted we wouldn’t do a nuclear deal without the hostages too. Once the nuclear deal got mired in various obstacles and setbacks, the US moved to separate these two tracks. Unfortunately, Iran’s own internal turmoil and politics made finalizing a deal very difficult. Eventually, in the spring of 2023 we saw an opportunity to get it done as Iran acknowledged a return to the nuclear deal wouldn’t happen in the near term. You signed the agreement in the summer of 2023 and completed the prisoner swap on September 18, 2023. But implementation was very messy.
Abram: We spent months in negotiations and indirect engagements in the run-up to the deal. Qatari officials would shuttle between my team and the Iranian delegation in separate hotels within view of each other in Doha. Ultimately, signing the deal was relatively easy, but then the real work began. Finalizing the technical process for transferring the restricted funds from South Korea to Qatar was nothing short of a nightmare and couldn’t be completed until after a deal was signed. Private banks wanted no part of a complicated arrangement without ironclad guarantees from the US government. We also needed to ensure the funds could not be inappropriately accessed by Iran, so this resulted in a multistep process that ended up involving political leaders, central banks, and regulators, as well as private correspondent banks and their boards across more than half a dozen countries in Asia and Europe. Every step was time-consuming and cumbersome, as we had to coordinate an interagency effort of sanctions, banking and finance, regional experts, and lawyers to create the mechanism to move the funds. It might sound boring, but we all knew the stakes were high. If we couldn’t get it done, these Americans would not get home to their families.
I have been involved in other complex negotiations—including the effort in 2021 that secured the release of the two Canadian citizens and an American detained by China—and none of them were simple. But Iran presented a distinct implementation challenge. The United States has no embassy in Tehran, no formal diplomatic channel, and no reservoir of institutional trust to draw upon when disagreements arose. It made the entire process much harder.
Nate: My role in this process was to periodically check in on you and the Treasury Department and make sure you all were on top of the issue. And you were. But the main takeaway was that proper implementation required a tremendous amount of highly technical work. That stuff doesn’t just happen on its own.
The other major challenge we had to work through was the unexpected detention of a fifth American citizen after we had already finalized a deal for the first four. This was a massive complication. We were desperate to get the four Americans home, but our leadership wasn’t going to leave the fifth behind. We essentially had to rework the arrangement in real time, get the family of the fifth hostage to agree to join our deal and simultaneously make Iranian leadership understand that we weren’t moving forward without the fifth person while trying not to delay implementation of the initial deal. Leadership at the State Department and the NSC were highly involved in the process, but it felt like it could fall apart right up until the swap.
Abram: Exactly. Even on the day of the swap, Iran tried a last-minute curveball. I was on the tarmac in Doha, hours away from the Americans’ release and with international press already broadcasting live, and Iran tried to renegotiate the legal terms of the release of the Iranians who were being released from the US and claimed they were unable to locate the officials in their judicial system responsible for the final steps of releasing the Americans from Iran.
Nate: I still believe Iran was just stalling because Cristiano Ronaldo was in Iran that day and using the VIP airport terminal.
Abram: Haha, maybe, and it was jarring to watch Ronaldo walk out of the terminal in front of the cameras as we were waiting for Iran to move the Americans through their airport. But their demand for last-minute concessions was not a surprise to either of us or our team. Iran has a habit of using the public spotlight to push for additional last-minute concessions by betting that Washington will be reluctant to walk away. They were not wrong that we desperately wanted those Americans home after years of wrongful detention. They were wrong that we had no leverage to refuse. We had spent months building contingencies precisely for this moment, identifying which partner governments could apply pressure—in this case the Qataris—and what our walk-away point was. Because we had an interagency system in place to respond to these demands within a matter of minutes, we were able to hold firm, and the deal proceeded as originally agreed.
Lately I have been thinking a lot about this question: What would you have done differently in retrospect?
Nate: I have two major regrets from my time as director for Iran at the NSC, including one specifically related to the hostage deal. As part of the deal, Treasury and State developed an airtight mechanism to ensure the funds were used exclusively for humanitarian purposes (food and medicine). After Hamas attacked Israel on October 7, 2023, we asked Qatar to not process any transactions. The politics and rationale of the move were understandable (and I fully supported them at the time), but it will make future diplomacy with Iran more difficult. In the last eight years, the US has withdrawn from a complex nuclear agreement, failed to fully implement the 2023 hostage deal, and bombed Iran amid negotiations in 2025 and 2026. US actions do have consequences, and it will limit the ability to conduct effective diplomacy moving forward.
My second regret is my belief that we could “manage” the Iran challenge. I wouldn’t change any one specific action, but it was more the mindset for how I addressed the issue. For instance, it was clear by early 2023 that we weren’t going to return to the JCPOA. There were good reasons for this. Iran’s technical gains greatly reduced the value of the agreement, and Iran had missed multiple opportunities to get back in the deal. My assumption was that we could manage the problem—and we mostly did. We used a combination of pressure, inducements, and dialogue to successfully avoid escalation with an eye toward 2025 as a new opportunity for a more ambitious policy. However, in retrospect, I falsely assumed we could account for and manage a litany of unknown variables. The United States did not—and could not—account for the Hamas attack, Israel’s counter-response, and ultimately the ill-conceived war with Iran.
Abram: You raise two important issues, both central to the future of diplomacy. Over the years, there has undoubtedly been a deficit of trust between the United States and Iran, often for good reason. The last several years, including the implementation of the hostage deal, has undoubtedly further complicated the ability of any overarching deal to solve the problems in the relationship. Like you, I’m not sure there would be a better way to handle it at the time, but it undoubtedly creates additional complications now. In many ways, I’d say it redoubles the importance of intermediaries and partners to help bridge the glaring gaps in trust.
I see the approach to “managing” Iran or any foreign policy challenge a little differently. In many ways, “managing” the situation was the best option we had, as is often the less politically appealing but realistic approach to intractable problems. But you raise an interesting point on the ability of the US to “manage” certain foreign policy issues. In the context of Iran, some critics called this the “no deal, no crisis” mindset. I don’t disagree that this approach is not ideal, but I think there’s an important corollary. “Managing” a foreign policy issue like Iran or, say, competition with China, is in some ways even more difficult and arcane than reaching a deal. A fundamental part of US diplomacy and foreign policy is managing the status quo when it suits US interests and there is no clear-cut solution available in a deal, military campaign, or other policy option. In my view, it’s easier to do something big and splashy—get a deal, start a war—than it is to “manage” a problem. It takes a concerted interagency effort, resources, and attention.
Nate: This brings us up to the current moment. The administration appears to be on the verge of signing a framework for an agreement with Iran. We don’t know the details, but it is reportedly focused more on ending the war, potentially reopening the Strait of Hormuz, and a commitment to future negotiations than on presenting a fully fleshed out deal. While I welcome the end of the war, it is hard to say anything definitive until we know more. But regardless of what does emerge, there are some obvious and readily apparent lessons from 2023 that apply to today. Details matter, implementation is often more difficult than merely agreeing to a deal, and it takes a lot of good people to get stuff done. What additional advice do you have for the administration?
Abram: I’d agree on all those points and would add two more. First, given the context and the challenges we’ve talked about, any deal now is unlikely to change the adversarial nature of the United States’ relationship with Iran overnight. On September 18, 2023, five Americans walked onto a US government plane in Doha and came home to their families. That was worth every ounce of criticism we received over the deal, every frustrating call with a financial institution in Europe, and every last-minute Iranian curveball. But the morning after, the Islamic Republic was the same regime it had been the day before. This is not an argument against diplomacy; it’s an acknowledgement that advancing US interests means we can’t pick — or easily change — who is sitting at the table across from us and that the work isn’t done once a deal has been inked.
Second, the administration should resist the temptation to declare victory at the signing ceremony. That is when the real work begins, including the interagency coordination, the technical implementation, and Iran inevitably testing the bounds of the agreement. The question is not whether Iran will push back. It is whether the people responsible for holding the line will have the resources, the authority, and frankly the attention to implement the deal after the press has stopped paying attention and world has moved on to the next challenge.