How many times were the US and Iran on the verge of a deal?

Secretary of State Marco Rubio sounded unequivocal this week in telling Congress that the U.S. will not grant Iran any sanctions relief or access to frozen assets solely for reopening the Strait of Hormuz.

Parse Rubio’s words, though, and you’ll find a potential escape hatch.

Maybe the U.S. won’t ease “sanctions” on Iran’s Islamist regime, and maybe it won’t let Tehran have access to billions in “frozen” assets. But what about “restricted” Iranian funds? That’s a whole other category, at least $6 billion reportedly held in Qatar alone, that cash-strapped Iran wants.

The U.S. had previously deemed such assets usable by Iran for limited purchases, but it asked that banks stop their release due to the Israel-Hamas war. A quiet U.S. nod now could allow for workarounds that let Iran indirectly use this money without technically violating American sanctions or touching funds labeled “frozen,” former U.S. officials familiar with sanctions law told me.

This approach to getting the strait reopened would be sneaky and misleading.

It would also be standard diplomacy.

To lure Iran into a broader deal that covers its nuclear program, any presidential administration, not just one led by Donald Trump, a man who routinely lies, would likely have to rely on many more such deceptions.

“The fundamentals of diplomatic negotiations often require a suspension of disbelief,” said Alex Zerden, a former Treasury Department diplomat who has worked for both Republican and Democratic administrations.

I am not endorsing dishonesty here. But it is hard to find successful major diplomatic negotiations in history that didn’t require some level of deceit or, at least, intentional confusion.

Such maneuvering isn’t just about public relations. It can be crucial to resolving or at least getting past what feel like irreconcilable differences.

In the 1970s, when the U.S. was reorienting its Asia policy to recognize the authorities in Beijing as the sole legal government of China, it said it “acknowledged” Beijing’s position that Taiwan was part of China. But the U.S. also said “acknowledge” did not mean that it agreed with Beijing’s position or was adopting it. This is a key part of the One China Policy.

Such wordplay has allowed Washington and Beijing to maintain a relationship, if not a perfect one, for decades since, while allowing Washington and Taipei to also have less official ties.

In today’s intensely polarized politics, it’s arguably harder to get away with such maneuvering. A seemingly endless number of interested factions are watching every move and determined to affect the outcome. But it’s still necessary to use diplomatic acrobatics to come to terms with an adversary, former U.S. officials tell me.

The Iran talks under President Barack Obama had their issues, but they also provide examples of how an administration can use sleight of hand to manage perceptions. Trump might find lessons there, if he wanted to look.

One flashpoint in that nuclear negotiation revolved around what were, officially, two side arrangements. One led Iran to release several U.S. citizens it had imprisoned, and one resolved a decades-old U.S.-Iran financial dispute by having the U.S. pay Iran an overall sum of $1.7 billion.

Obama aides insisted that these deals were separate from the nuclear talks and had nothing to do with each other.

But it’s hard to imagine that these arrangements would have come together had the nuclear talks failed. In fact, the U.S. payment and the prisoner releases took place the same weekend the nuclear deal was formally implemented in January 2016. The Obama administration also wouldn’t release the first installment of what it owed to Iran, around $400 million, until after the American prisoners were safely away from Tehran.

This led Republicans to allege that the Obama administration had paid a ransom to Iran, even though U.S. officials claimed the money transfer had nothing to do with the prisoners.

The final 2015 nuclear deal was itself structured in a way that could let both Iran and the U.S. claim victory.

The U.S. could say its sanctions on Iran weren’t technically eased until after Tehran had dismantled much of its nuclear infrastructure, while Iran could say the deal didn’t formally take effect until after the U.S. had lifted the sanctions.

Everyone wins, right?

For years, Trump trashed the 2015 deal, in particular the “pallets of cash” sent as the prisoners were released, calling it “horrible” and “dangerous” and alleging it would help Iran get a nuclear weapon as opposed to blocking it from doing so. In 2018, as president, Trump pulled the U.S. out of the deal.

Now, Trump appears perturbed by the possibility that he might have to strike a similar deal with Iran and determined to come out ahead in any comparison.

Luckily, Trump is uniquely capable of the contortions such an agreement would require. He has, at best, a “situationship” with the truth. This is, after all, a man who still insists he won the 2020 election and claims to have ended wars that were not wars.

“Since when has truth-stretching been a deal-breaker in Trumpian diplomacy?” asked Rob Malley, who dealt with Iran in both the Obama and Biden administrations.

We’ve already seen the Trump team ignore the inconvenient when it comes to Iran. In the early days of the war, it effectively eased sanctions on Iran by issuing waivers that let Tehran sell oil already at sea. The administration’s goal was to calm energy markets roiled by the conflict.

When I asked the White House for comment on Trump’s approach, spokesperson Olivia Wales said: “President Trump is a master negotiator with a proven track record of achieving good deals, and he will only accept one that puts America first and never allows Iran to have a nuclear weapon.”

There are any number of ways Trump can spin a future Iran deal to his benefit.

If Iran agrees to use a line of credit to gain access to its financial assets, Trump can argue that, unlike Obama, no cash was exchanged. If Iran agrees to zero enrichment of uranium for even a brief amount of time, that, too, could be spun as a key concession. If Trump lets Iran somehow earn money off of ships’ use of the strait without officially charging a toll, he could cast that as an acceptable tradeoff.

If Iran repeats, as part of a memorandum of understanding on how talks will proceed, that it will never pursue a nuclear weapon, Trump can call that an early concession. Iran has made such declarations numerous times for many years, but, in fairness, there is new regime leadership in Tehran.

If Trump speaks directly with Iran’s new supreme leader, Ayatollah Mojtaba Khamenei, that’s one way he can argue he is more influential than other U.S. presidents, even if the conversation leads to no change in Iranian policy. The late supreme leader, Ayatollah Ali Khamenei, Mojtaba’s father, never directly spoke to a U.S. president.

The elder Khamenei was killed in the war’s early hours. A face-to-face meeting with Mojtaba is unlikely, despite Trump’s recent suggestion that he’d like one, given the decades of animosity between the two countries and the peculiarities of Iran’s theocratic system.

I wouldn’t put it past Trump to call any agreement with Iran a “treaty,” not because it would ever reach the Senate (which the term would imply) but because Trump wants it to be remembered that way.

To be fair, precision and accuracy have often gone out the window when it comes to Iran and the nuclear talks in particular. How do you explain, in simple terms, that the 2015 deal was a “political arrangement,” not a legally binding accord? How many Americans believe Obama lifted all U.S. sanctions on Iran when in reality he left in place numerous non-nuclear sanctions? And what really counts as a “sanction” these days anyway?

The Trump team can’t even get its story straight on whether the U.S. is at “war” with Iran right now.

The State Department didn’t respond to my questions about Rubio’s testimony on what the U.S. would do regarding the strait. While he rejected the idea of lifting sanctions or handing over frozen funds, Rubio told Congress the U.S. would lift its blockade on Iranian ports if Tehran releases its grip on the strait.

While Trump may be fine with deception and spin, he struggles to stay quiet when negotiations are in process and need to remain confidential.

He and his aides’ constant dribbling out of information could erode trust with Tehran, some former U.S. officials told me.

“Every step of the way they are leaking everything to the press. You don’t do that if you actually want a deal to happen,” said Ilan Goldenberg, who worked on Middle East issues for the Obama and Biden administrations.

When it comes to Iran, where saving face is an important part of the culture, Trump may also need to clamp down on his urge to dominate his foes.

Both sides will spin any agreement to their advantage in public. What’s critical, though, is that in private they are in lockstep when it comes to the mechanics, such as who will make what move when, and what every word agreed to actually means.

“There will be dueling interpretations and ambiguities in the public presentation of any agreement,” said Nate Swanson, a former U.S. official who dealt with Iran under both Democratic and Republican presidents. “The hope is that there will be a clear understanding between the parties themselves as to how to implement a deal.”