Letters to the Ayatollah: Why Obama’s Latest Outreach to Iran’s Supreme Leader Was A Mistake

With a deadline for the Iranian nuclear negotiations set to expire in a few weeks and significant differences still outstanding, President Barack Obama reportedly penned a personal appeal to Iran’s supreme leader, Ayatollah Ali Khamenei, last month. The move betrays a profound misunderstanding of the Iranian leadership, and is likely to hinder rather than help achieve a durable resolution to Iran’s nuclear ambitions as well as other U.S. objectives on Iran.

If the reports are accurate — and the administration has not yet confirmed the scoop by the Wall Street Journal — the letter apparently urged Khamenei to finalize the nuclear deal and dangled the prospect of bilateral cooperation in fighting the Islamic State group (also known as ISIS or ISIL) as an incentive. It marks the fourth time since taking office in 2009 that Obama has reached out to Khamenei personally, in addition to his exchange of letters (and an unprecedented phone call) with the country’s president, Hassan Rouhani.

This constitutes a striking increase in American outreach to the Iranian leadership since the revolution. The two countries have not had direct diplomatic relations since April 1980, and have engaged in direct dialogue only sporadically since that time, most recently in concert with five other world powers in talks aimed at eliminating Iran’s path to nuclear weapons capability.

In dealing with one of the world’s most urgent crises, more direct dialogue is surely a net positive. But the technique and tactics matter, perhaps even more in this interaction than in most other disputes, where contact is more routinized and where there is a more substantial foundation of mutual understanding or at least familiarity. It makes perfect sense, for example, that the U.S. military has apparently utilized Iraqi officials as an intermediary on issues related to the ISIS campaign, which Tehran has waged independent of the U.S.-led effort through its proxies on the ground in Iraq.

However, it is precisely at the tactical level that an Obama letter to Khamenei at this juncture appears so spectacularly ill-conceived. First of all, it poses no realistic possibility of advancing progress in the nuclear talks or any other aspect of U.S.-Iranian relations. After all, only the most naïve and uninformed observer of Iran would believe that a personal appeal from Obama would sway the Supreme Leader in a positive fashion.

Khamenei’s mistrust and antipathy toward Washington has been a consistent feature of his public rhetoric through the 35-year history of the Islamic Republic. He has described Washington with every possible invective; he indulges in Holocaust denial and 9/11 conspiracies; and he routinely insists that the United States is bent on regime change in Iran and perpetuating the nuclear crisis. These views are not opportunistic or transient. Anti-Americanism is Khamenei’s bedrock, engrained in his worldview, and as such it is not susceptible to blandishments — particularly not from the very object of his loathing.

Moreover, the Islamic Republic’s leadership is steeped in a Hobbesian understanding of the international system; as a hardline newspaper wrote, “our world is not a fair one and everyone gets as much power as he can, not for his power of reason or the adaptation of his request to the international laws, but by his bullying…” Interpreted in this context, Obama’s appeal to Iran’s highest power at this critical juncture in the nuclear diplomacy will surely be read as a supplication — and as further confirmation of American desperation and weakness in the face of Iran’s position of advantage.

This may sound absurd, given the relative disparity in the two countries’ capabilities and international influence. And by any objective standard, Iran has a more compelling interest in a swift resolution to the longstanding nuclear impasse, since a deal would begin to curtail the devastating sanctions that have halved Iran’s oil exports and stranded its earnings in foreign banks that are off-limits to the Iranian treasury.

But Tehran has long sought to convince itself and the world otherwise. Khamenei himself regularly revels in his conviction that America is on the retreat in the face of Iran’s superior power. As he explained recently “the reason why we are stronger is that [America] retreats step by step in all the arenas which we and the Americans have confronted each other. But we do not retreat. Rather, we move forward. This is a sign of our superiority over the Americans.”

In addition, the incentive that Obama apparently proffered in his latest correspondence — a willingness to explore the confluence of interest between Tehran and Washington on combatting Sunni extremists — offers very little prospect of meaningful traction. The simple reality is that neither side prioritizes the ISIS battle over the nuclear diplomacy, as evidenced by the fact that Iran’s diplomats sought to use the same implicit linkage to lure Washington into greater nuclear concessions. Meanwhile, Iran’s security establishment has categorically rejected speculation about direct cooperation with the U.S.-led campaign, preferring to pursue its own offensive and convinced (probably correctly) that Tehran and its proxies have the upper hand in both Iraq and Syria.

As a result, there is simply no plausible scenario in which a letter from the President of the United States to Ali Khamenei generates greater Iranian flexibility on the nuclear program, which the regime has paid an exorbitant price to preserve, or somehow pushes a final agreement across the finish line. Just the opposite — the letter undoubtedly intensified Khamenei’s contempt for Washington and reinforced his longstanding determination to extract maximalist concessions from the international community. It is a blow to the delicate end-game state of play in the nuclear talks at the precise moment when American resolve was needed most.

The revelation of the letter also undercuts Obama elsewhere. It deepens tensions with America’s regional allies, whose assistance in strengthening the Sunni opposition to ISIS is sorely needed. It also hurts him at home, and again at the worst possible time, given the mid-term elections’ outcome and incoming Republicans majorities in both houses of Congress. Obama’s rivals on Capitol Hill were already planning an activist agenda on Iran that could disrupt the administration’s diplomatic efforts; the letter will be seen — wrongly — as confirming the right’s most ludicrous conspiracy theories about a covert American-Iranian alliance.

It is difficult to imagine the logic that inspired Obama’s latest missive, other than an utter ineptness in understanding Iranian political dynamics. However, it is consistent with prior mawkishness that the administration has demonstrated toward Iran’s leadership during Rouhani’s two visits to New York for the United Nations General Assembly meetings — an unseemly, artless pursuit of some personal affinity in hopes of advancing bilateral diplomacy.

Obama would hardly be the first American president to delude himself that he can overcome international conflicts through the force of his own charisma — recall, for example, President George W. Bush’s excruciating assertion that he had looked into the eyes of Russian leader Vladimir Putin and sensed his soul. But he might just be the first to fumble a crucial arms control agreement near the finish line out of a misguided overconfidence in the power of his own prose.