Engaging Iran: Does Trump have a real plan?

For obvious reasons, in the ever-turbulent saga of U.S.-Iran relations, President Trump’s claim to have sent a letter to Iran’s supreme leader, Ayatollah Ali Khamenei, is the latest twist in a long-running drama. Trump’s announcement, made during a Fox Business interview, was characteristically brash.

“I wrote them a letter saying, I hope you are going to negotiate,” he said, adding that Iran could either “handle” the U.S. militarily or “make a deal.”

The president’s remarks were accompanied by his trademark mix of threats and vague promises, leaving observers to wonder whether this was a genuine diplomatic overture or merely another piece of political theater. Trump stated, "I wrote them a letter saying, I hope you are going to negotiate," before veering into an awkward gaffe — referring to "Khomeini" instead of Khamenei, mistakenly invoking the name of Iran’s long-deceased revolutionary founder.

Media reports claim that the letter had been "written" but not sent, while Iran’s government officials flatly denied having received any such correspondence. This episode underscores the performative nature of Trump’s diplomacy, where grand gestures often precede — or outright replace — substantive engagement.

This is not the first time a U.S. president has attempted direct outreach to Iran’s supreme leader. Barack Obama, in a more serious effort at diplomacy, sent two letters to Khamenei. Even Trump previously relied on intermediaries, such as former Japanese Prime Minister Shinzo Abe, who in 2019 delivered a message to Tehran only to have Khamenei reject it outright.

The leader’s refusal reflected a deep-seated distrust that has only grown since Trump unilaterally withdrew from the Obama administration's Iran nuclear deal — the Joint Comprehensive Plan of Action in 2018 — dismantling years of multilateral negotiations and reimposing crippling sanctions on Iran. The timing of Trump’s claim about the letter is notable. Trump’s approach also suffers from a fundamental contradiction. On the same day he spoke about his desire for negotiations, Treasury Secretary Scott Bessent, promised even harsher economic restrictions on Iran.

Speaking at the Economic Club of New York, Bessent vowed that a second Trump administration would "shut down Iran’s oil sector and drone manufacturing capabilities" and further sever the country’s access to the international financial system.

This contradiction — the offer of dialogue alongside threats of escalated economic warfare — only further reinforces Iran’s skepticism toward any overtures from Washington. The Iranians have been very clear that they will not negotiate while being pressured. Khamenei has often called the talks with the U.S. “unwise, unintelligent and dishonorable” and this is in concordance with the cultural disposition of the Iranians who have been brought up to suspect the West. 

From the 1953 CIA-sponsored coup that restored the Shah to the imposition of sanctions, Tehran has never seen Washington as anything but a country that wants only to take and has no intention of giving in return.

Trump has always had a combination of threat and compromise with respect to Iran. Although he claims to have a primary interest in preventing Iran from acquiring nuclear weapons, his actions suggest something different. After throwing away the nuclear deal — an agreement that put the most stringent nuclear material oversight program on Iran — Trump effectively pulled away the very mechanism of ensuring Iranian compliance. Instead, his administration adopted a policy of maximum pressure to induce Iran to give up its missile program and cut ties with regional powers such as Hezbollah and the Houthis.

Publicizing a letter before it reaches its intended recipient is an unusual diplomatic move, one that analysts suggest is more about optics than genuine diplomacy. If Trump were serious about negotiations, he would not simultaneously be threatening military action or boasting about crippling sanctions. Iran, having weathered years of economic isolation, is unlikely to be swayed by media theatrics.

Moreover, there is no clear evidence that Trump’s military threats carry much weight. A full-scale U.S. attack on Iran’s nuclear facilities would be quite challenging due to the fact that the country has spread out its nuclear facilities. Any such action would inevitably lead to a severe Iranian counter-response and further escalate the conflict in the region and beyond. The risks are much higher than the potential gains, and yet Trump continues to wield the threat of force as a rhetorical tool.

The broader context of U.S.-Iran relations suggests that Trump’s latest maneuver is unlikely to yield results. Washington’s withdrawal from the nuclear deal not only alienated Iran but also fractured Western unity on the issue. While European signatories initially attempted to salvage the deal, they eventually began imposing their own restrictions on Tehran, contributing to its slow demise.

In response, Iran started rolling back its own commitments in 2020, having concluded that the West had already abandoned its obligations. Iranian leaders, meanwhile, remain defiant. Foreign Minister Abbas Araqhchi dismissed reports of Trump’s letter, stating unequivocally that no such communication had been received. Iranian Parliament Speaker Mohammad-Baqer Qalibaf reinforced this stance, emphasizing that Tehran will not rely on U.S. engagement to resolve its economic challenges. Instead, he argued that Iran should focus on strengthening its domestic economy and fostering ties with non-Western powers.

Trump, for all his self-styled deal-making prowess, has yet to demonstrate a coherent strategy for dealing with Iran. His approach oscillates between threats and vague promises of negotiation, all while deepening Iran’s economic and military resolve. If his goal is to prevent Iran from advancing its nuclear program, his policies have thus far achieved the opposite. By dismantling the Iran nuclear deal, he removed constraints on Iran’s uranium enrichment.

By imposing harsher sanctions, he strengthened hardliners in Tehran who argue that engagement with Washington is futile. Iran’s response to Trump’s letter — whether real or imagined — reflects a broader trend in its foreign policy. The Islamic Republic has long viewed negotiations with the U.S. as a trap, a means for Washington to extract concessions without offering meaningful guarantees. This perception has only hardened in the Trump era, with officials across Iran’s political spectrum voicing deep skepticism toward any overtures from Washington.

As Trump continues to flirt with the idea of renewed talks, the reality remains unchanged: meaningful diplomacy requires trust, consistency, and a willingness to compromise — qualities that have been in short supply these days.

Imran Khalid is a physician and has a master’s degree in international relations.