As if President Donald Trump isn’t busy enough taking a woodchipper to the federal bureaucracy, threatening to wage economic war in North America, putting the screws on Ukrainian President Volodymyr Zelenskyy to pressure him into peace talks with Russia and giving impromptu interviews in the Oval Office every other day, he has added another weighty item to his “to-do” list: negotiating a nuclear agreement with Iran.

During an interview with Fox News, Trump let it be known that he sent a letter to Iran’s supreme leader, Ayatollah Ali Khamenei, to begin a line of communication. The gist of the missive was clear enough: I’m interested in striking a deal with you on Tehran’s nuclear program, but if you refuse to come to the table, there will be trouble.

“Something is going to happen one way or the other,” Trump said after revealing news of the letter. “I hope that Iran, and I’ve written them a letter, saying I hope you’re going to negotiate because if we have to go in militarily, it’s going to be a terrible thing for them.”

This isn’t the first time Trump has openly expressed his desire to engage in diplomacy with Iran. Even during his first term, when his administration enacted a yearslong maximum pressure campaign that drove Iran’s crude oil exports down by 75%, Trump flirted with the prospect of negotiations.

In September 2019, on the sidelines of the annual U.N. General Assembly meeting, Trump was waiting for Hassan Rouhani, the Iranian president at the time, to pick up the phone, much as Rouhani did with Barack Obama six years earlier. The conversation with Trump, however, never occurred; Rouhani wasn’t keen on becoming Iran’s version of North Korean leader Kim Jong Un, who sat with Trump for two summits with nothing to show for it.

In the days since Trump sent his letter, not much has changed in Iran’s outlook. Khamenei, the man who will decide whether or not Tehran re-enters a diplomatic track with Washington, told the Americans to shove it.

The Supreme Leader clearly has 2018 stuck in the back of his mind, the year when Trump withdrew the U.S. from the Barack Obama-era Joint Comprehensive Plan of Action (colloquially referred to as the “Iran nuclear deal”) and re-imposed the very sanctions Washington lifted a few years prior. As the old saying goes, “fool me once, shame on you. Fool me twice, shame on me.”

This isn’t the answer Trump wants to hear, but he can’t be surprised by it either. One of the Trump administration’s first foreign policy acts upon reentering the White House on Jan. 20 was an executive order reinstituting the maximum pressure policy in the hope of driving Tehran’s oil exports to zero (the definition of an impossible task).

The Treasury Department has announced several sanctions on Iran since early February. In fact, the second Trump administration is going further on the sanctions front than it did during the first; the previous U.S. waivers permitting Iraq to pay Iran for electricity supplies are no longer available. Trump officials are also currently deliberating over a policy that would enlist other countries in an effort to stop Iran from exporting its crude at sea by seizing ships carrying Iranian barrels.

The Iranians obviously won’t take kindly to any of these moves. Although the Trump administration and Iran hawks in Congress consistently make the point that the stick is the only thing that will drive Tehran to the negotiating table, history doesn’t support this common talking point.

In reality, the more pressure the U.S. brings to bear on Iran economically, politically and militarily, the more likely Iran will escalate rather than submit. We need to look no further than Trump 1.0.

The U.S. at the time assumed that if the Iranian government suffered enough financial strain, Khamenei would have only one option if he wanted to save his regime: crawl back to the negotiating table and give the Americans everything they asked for.

Washington was so confident the Iranians would eventually cave that then-Secretary of State Mike Pompeo outlined a series of demands about as idealistic as they were preposterous — no more enrichment at any level, an end to missile production, the withdrawal of all support to Hamas, Hezbollah and Palestinian Islamic Jihad, the demobilization of Iranian-backed Shia militias in Iraq and a cutoff of military support to the Houthis in Yemen.

Needless to say, Khamenei rejected this proposal about as quickly as an 8-year old rejects broccoli. Iran used Trump’s destruction of the JCPOA as an opportunity to boost enrichment to new heights and install more advanced centrifuges. International inspectors, who once had the power to monitor Iran’s nuclear fuel production cycle from its very inception, were now forced to make do with far less access.

When the International Atomic Energy Agency censured Iran for stonewalling its investigation, Iran retaliated yet again by removing the cameras and barring some of the most qualified IAEA technicians from entering the country. Iran’s nuclear work only accelerated during Joe Biden’s term, partly as a consequence of his administration dropping formal nuclear talks after the Iranians cracked down on domestic protests. The result: Iran now has enough nuclear fuel to make six bombs if it chooses to do so.

This is the problem Trump inherits. I think his interest in diplomacy with Iran is sincere. But in the grand scheme, that’s far less important than whether Trump has the political will to offer the concessions required to get to an agreement and whether he can settle for anything less than the ideal. Don’t let the perfect be the enemy of the good.

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Daniel DePetris is a fellow at Defense Priorities and a foreign affairs columnist for the Chicago Tribune.

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