Donald Trump has long had a penchant for correspondence, a trait evident during his first term as President of the United States. Notably, he engaged in a substantial exchange of letters with North Korea's leader, Kim Jong Un, resulting in 27 letters over just 16 months. Additionally, he composed a memorable message to Turkey’s President, Recep Tayyip Erdoğan. As his second presidential term unfolds, Trump has surprisingly found a new pen pal: Iran's Supreme Leader, Ayatollah Ali Khamenei.

In early March, a high-ranking diplomat from the United Arab Emirates facilitated the delivery of a letter from Trump to Khamenei. This diplomatic communication has since been reciprocated, with Iran sending Khamenei’s response through its intermediary of choice, the Sultanate of Oman. The contents of this letter are said to be detailed and strategic, leaving the door open for potential negotiations. A source familiar with the Iranian political landscape disclosed this information on the condition of anonymity, emphasizing the sensitivity of these discussions.

Just two months prior, Khamenei publicly declared that engaging in dialogue with the United States was “neither rational, nor smart, nor honorable.” This statement aligned with his longstanding stance during Trump's first term; in 2018, he firmly stated that Iran would “never” engage with the Trump administration. A pivotal moment occurred in June 2019, when Japan’s Prime Minister, Shinzo Abe, traveled to Tehran bearing a letter from Trump, only for Khamenei to dismiss the gesture, proclaiming the U.S. president unworthy of a response. Moreover, despite the logistical efforts of French President Emmanuel Macron to organize a videoconference between Trump and then-Iranian President Hassan Rouhani, the meeting ultimately did not materialize.

In the past, however, Khamenei has shown a capacity for compromise, often reframing his decisions as strategic retreats. This concept of 'heroic flexibility' originated from his admiration for a Shiite imam who chose peace with a former adversary. Khamenei invoked this phrase in 2013 to justify Iran's negotiations with the Obama administration, which had commenced with a similar exchange of letters between then-President Barack Obama and the Supreme Leader.

Despite his advanced age of nearly 86 and a deeply ingrained animosity towards the U.S., Khamenei faces significant domestic challenges. Iran's economy is under severe strain, with rising public discontent. Trump's consistent message to Iran has remained clear: engage in dialogue, agree to halt nuclear weapon pursuits and cease support for regional militias, and in return, the U.S. will allow Iran to prosper. Should Iran refuse this opportunity, Israel, emboldened by its recent military successes against Iranian-aligned groups like Hamas and Hezbollah, may consider military action against Iran's nuclear facilities. Furthermore, Trump’s previous policy, dubbed “maximum pressure,” threatens to inflict further economic damage on Iran, particularly targeting its oil trade with China, which constitutes a vital source of foreign currency.

The impact of these pressures is evident. Currently, the U.S. dollar trades for over 1 million Iranian rials, marking an increase of nearly 75% in just a few months. This drastic depreciation ranks the Iranian currency among the most devalued globally. The extreme economic situation thus provides a compelling incentive for Iran to engage in negotiations. However, Khamenei is acutely aware of the precariousness of his position, leading him to project an image of toughness. In a recent Eid al-Fitr address, he maintained that Iran's positions remain unchanged, despite the perceived threats from the U.S. and Israel. He warned of a “firm blow” in response to any attacks, although he noted that such an attack was “not very likely.” He reiterated the longstanding Iranian commitment to the destruction of Israel, stating that all nations have a collective duty to work towards eliminating it from the region.

This rhetoric is not isolated; other Iranian military leaders have issued similar threats against American bases throughout the region. Ali Larijani, a centrist politician and Khamenei’s advisor, claimed that while Iran has no intention of developing nuclear weapons, it could be compelled to do so if attacked. Though these statements may come across as aggressive, they serve more as a tactical maneuver in negotiations than actual declarations of intent.

Larijani has expressed hope for “tangible results” from diplomatic efforts with the U.S., even praising Trump as a “talented businessman.” Other Iranian officials have echoed these sentiments, despite expressing grievances about what they term Trump’s “bullying” and threats of military action. Iran's Foreign Minister, Abbas Araghchi, recently asserted that Iran is “always ready to negotiate on an equal footing,” signaling that the initiative now lies with the U.S. A top communication official in President Masoud Pezeshkian's office reiterated that the onus is on the U.S. to respond positively.

Iran’s mixed signals may stem from a dual strategy of preparing for both diplomacy and confrontation. Mostafa Najafi, an expert on Iranian security matters, noted that Iranian authorities had reached out to Trump’s team even before his inauguration, indicating a preference for diplomatic solutions while simultaneously strengthening their defenses. Najafi indicated that Iran seeks a two-step process involving direct talks following current indirect communications, preferring to keep such discussions confidential. Iran aims to keep its missile and drone capabilities off the negotiation table, while showing willingness to discuss regional tensions. Nevertheless, he clarified that this does not imply compromising on their support for groups aligned with the Axis of Resistance.

This inclination towards dialogue resonates within Iran’s populace. Editorials in both business and political circles argue that Iran has little choice but to engage with the West. A recent online poll revealed that a striking 82% of respondents favored direct negotiations with the U.S., with only 11% opposed to any form of talks. Former Iranian ambassador Mohammad Ali Sobhani suggested that Iran might consider offering business opportunities to American firms to incentivize the Trump administration towards a deal.

Should Iran and the U.S. renew their discussions, various external factors could significantly influence the outcomes. Israel may attempt to dissuade Trump from pursuing negotiations in favor of military action aimed at keeping Iran weakened. Conversely, some voices within Trump’s circle appear to advocate for a more diplomatic route. Notably, media personality Tucker Carlson, who has maintained close ties with Trump, has vocally opposed military action against Iran. His exchange with Trump’s Middle East envoy, Steve Witkoff, which indicated an openness to dialogue, was closely monitored in Iran. The subsequent discussions surrounding diplomatic engagement have generated buzz in Tehran.

The political landscape has changed considerably since the Obama era when Arab allies in the Gulf were apprehensive about a nuclear deal with Iran. Now, these leaders are likely to counsel Trump against escalating tensions through military engagement, recognizing a need for stability in the region.

While Trump’s correspondence with Khamenei is unlikely to evolve into the type of personal rapport he established with Kim Jong Un, which ultimately faltered due to the absence of necessary technical negotiations, Iran is actively attempting to reaffirm its commitment to the terms of the previous nuclear deal. The Iranian leadership seems to understand that if they wish to negotiate a new agreement with the U.S., they must adapt to Trump’s distinctive diplomatic style, which prominently features his preference for written communication.