Tehran’s Trump Trap

Tehran is setting a trap for the Trump administration.

Recent comments by Iran’s Supreme Leader Ali Khamenei have poured cold water on the idea of negotiations with the United States—or so it seems. Following President Trump’s inauguration, Khamenei issued a green light for talks and did not oppose the full-court press from his officials promoting negotiations.

So what gives?

Khamenei’s backtracking and balancing has deep roots and was on full display amid nuclear negotiations during the Obama and Biden years. Khamenei covets power without accountability, often deflecting or caveating big policy decisions like deal-making with the United States. While his latest comments will severely limit political room for maneuver in Tehran, they do not mean that the Islamic Republic won’t talk.

Keen to take advantage of Trump’s oft-repeated desire for a deal, Khamenei is actually upping the asking price while his officials coyly dangle diplomacy. Negotiations here are not a means of peacefully resolving the Iranian nuclear question but a tool to blunt the restoration of maximum-pressure sanctions while decreasing the chances of an Israeli or American strike.

After all, the Islamic Republic can ill afford to face four years of escalating economic sanctions or the prospect of a direct military conflict.

In the Middle East, Iran’s sole state ally, the Assad regime in Syria, has collapsed. Its terror proxies, Hamas and Hezbollah, have been dealt “several serious blows,” according to the regime’s foreign minister.

At home, Iran’s Russian-provided long-range strategic air defenses are crippled, thanks to a successful Israeli military operation. To make matters worse, an escalating domestic energy and currency crisis risks pushing an already frustrated and anti-regime population back out onto the street in protest.

To compensate, Iran is pushing its strategic partner China to buy more sanctioned oil while also stepping up its own inventory of enriched uranium—the fissile material needed to develop a nuclear weapon. It is also reportedly exploring faster pathways to developing a nuclear weapon. While these moves are how Tehran seeks to build leverage, it is hoping that Washington will misread its own weakness and fear as goodwill and restraint.

Elsewhere, Iranian proxies in Iraq have not struck U.S. positions in Iraq or Syria since November 2024, the month Trump was re-elected to the presidency. The Houthi rebels in Yemen, whom Tehran—and reportedly even China—have armed, recently released the crew of a tanker they had taken hostage well over a year ago.

Tehran has also released an elderly German-Iranian woman it held hostage for four years, cashed in on another round of “hostage diplomacy” with the Italians, and returned the body of another dual-national hostage it executed.

And here’s the ultimate role reversal.

To sweeten the prospects for negotiations with Trump personally, Iran’s president, Masoud Pezeshkian, has even tried to walk back Tehran’s plot to kill him, claiming, “We have never attempted this to begin with, and we never will.” This is in spite of FBI reports exposing an Iran-backed plot against Trump in 2024 and Iranian military officials re-upping a death threat against him in 2023.

The seeming about-face on all things Trump is the clearest indication of Iran’s sense of desperation. The Islamic Republic’s enmity with Trump is deep-seated, perhaps more so than with any other president in U.S. history. The reason is threefold.

First, Trump is the Western leader who broke the taboo of supporting the Iranian people each time they poured out into the street to protest against their clerical overlords. Trump’s strident comments and tweets from 2017 to 2020 contrast sharply with President Obama’s tepid response to protests in 2009, which forced demonstrators to chant, “Obama, Obama, are you with us or them?”

Prior to Trump, Western support, even if only rhetorical, was long believed to be a “kiss of death.” Following Trump, dissident leaders have much more forcefully embraced the bully pulpit and even sanctions.

Second, Trump’s maximum pressure policy in his first term was extremely effective, with Iranian officials calling it more economically devasting than the regime’s eight-year war with Iraq (1980–1988). Trump did record macro-economic damage to the Islamic Republic’s economy and oil exports in record time and unilaterally. This torpedoed the conventional wisdom that sanctions would have to be multilateral and phased to have a real effect.

And third, Trump is the U.S. president who pulled the trigger against Iran’s chief terrorist, Islamic Revolutionary Guard Corps Quds-Force chief Qassem Soleimani. “Soleimani’s shoe has more honor than the head of his assassin,” previously declared Khamenei. The move, which even the Bush administration allegedly shied away from, was both a strategical and psychological setback for Tehran, rendering it off balance in ways that were made clear against Israel in the post-October 7 Middle East.

For all these reasons, Iran’s mixed messages and entreaties are bait to bail out a faltering regime rather than indications of a genuine change in behavior.

Instead of hyping a deal and losing leverage, Trump can enhance his bargaining position by exploiting the Islamic Republic’s current sense of weakness. This can be done by intensifying sanctions, particularly on oil sales to China, while heightening Tehran’s fears over U.S. and Israeli military action, all while publicly downplaying the idea of talks. In other words, make the regime sweat and let maximum pressure commence.

Behnam Ben Taleblu is the senior director of the Iran program at the Foundation for Defense of Democracies (FDD).