When Iran's Supreme Leader Ayatollah Ali Khamenei declares: "In negotiations, one must be confident that the other party will fulfil its commitments. When we know they will not, what is the point of negotiating?" he is not merely recycling tired revolutionary rhetoric; rather, his position articulates a strategic calculus firmly rooted in a century of Iranian historical experience with American and Western diplomacy.

Khamenei’s wariness, which has defined Tehran's approach to Washington's recent overtures, stems less from ideological obstinacy than from two concrete wellsprings: a lengthy history of American interventions in Iranian domestic affairs (see Mosaddegh, Rafsanjani, the Shah) and the more recent experience of Washington's withdrawal from the nuclear agreement formally known as the Joint Comprehensive Plan of Action (JCPOA).

The historical dimension of Iran's distrust runs deep through the nation's political consciousness, which stretches far beyond that of Khamenei’s clique. Speaking to university students during a Ramadan gathering, Khamenei dismissed suggestions from domestic commentators that lack of trust should not prevent negotiations.

"This is incorrect," he insisted. "Even those two parties negotiating for peace must be confident in each other's adherence to the agreement; otherwise, they would not negotiate because they know it would be a futile, pointless exercise." This stance reflects a realpolitik assessment rather than mere revolutionary posturing. The Supreme Leader has often cited the cautionary tale of Prime Minister Mohammad Mossadegh, who in the early 1950s sought American support against British interests, only to fall victim to a coup orchestrated by the CIA’s Kermit Roosevelt in August 1953. "Mossadegh approached the Americans... he met with them, negotiated, made requests and trusted them," Khamenei recounted in November 2017.

"The 28th of Mordad (Iranian month) coup was carried out not by Britain but by America against Mossadegh," he said knowing how Mossadegh’s memory permeates both religious and secular Iranians. "They are not satisfied even with people like Mossadegh." For Iranian strategists, this history is not academic; it informs a contemporary understanding that America prefers compliant partners in the region. As Khamenei bluntly expressed it: "They want servants, vassals, people who take orders like who? – Like Mohammad Reza Pahlavi. They want someone of this nature to rule over this resource-rich, strategically important country."

The contemporary wellspring of Iranian scepticism derives from the collapse of the nuclear agreement, which Tehran views as the definitive proof of American diplomatic unreliability. "We spent years negotiating, and then this very person [Trump] threw out and tore up the completed, finalised, signed agreement. How can one negotiate with such a person?" Khamenei asked rhetorically. This experience has calcified into a doctrine that informs Iran's diplomatic strategy. "This experience showed us that we cannot sit and talk with America as a trustworthy partner on any issue," the Supreme Leader has stated. "Sometimes one can speak even with an enemy, but an enemy who adheres to his word and can be trusted not to renege on commitments for whatever reason."

The Iranian leadership's persistent reference to this episode suggests that the nuclear deal's failure represents more than a diplomatic setback; it serves as confirmation of a world view that regards American commitments with total and all-encompassing suspicion. His perspective did not emerge suddenly with the JCPOA's collapse. As early as November 2009, several months into Barack Obama's presidency, Khamenei noted: "The new American president said nice things; he repeatedly sent us messages, both verbally and in writing, suggesting we turn a new page, create a new situation, cooperate in solving the world's problems – to this extent!" But he remained cautious: "From the beginning of Farvardin [March 2009] when I spoke in Mashhad – I said if you wear a velvet glove over your iron fist and extend your hand, we will not extend ours; I gave this warning then – eight months have passed. During these eight months, what we have seen contradicts what they outwardly express."

Iranian officials consistently frame their approach to American diplomacy in terms of a broader strategic analysis about the nature of American interests in the region. In a meeting with government officials in August 2003, Khamenei identified what he considered the primary challenges facing Iran: "The formation of a united front against us, whose members are America and Zionism." He elaborated that "the united and central front working with all its might against the Islamic system has two members: the regime of the United States of America and the Zionist regime with its Zionist supporters throughout the world, whose power, wealth and influence across the globe are not insignificant." This framing places current diplomatic overtures within a historical context that Iranian leadership considers essential to understanding American motivations. "Iran was once America's footstool, and they could do whatever they wanted in this country. They controlled the economic affairs, they controlled cultural matters, important appointments and dismissals were in their hands; in fact, the government was in their control. They took, they consumed, they utilised; but now they have lost this advantage."

From Tehran's perspective, American diplomatic initiatives must be evaluated against this historical background rather than taken at face value. What Iranian officials may not know is that leaked US diplomatic cables reveal American negotiators were instructed to approach Iranians with the understanding that they would "not expect an Iranian readily to perceive the advantages of a long-term relationship based on trust" and to assume that their Iranian counterparts would "attempt to maximise the benefits to themselves that are immediately obtainable." These internal American assessments, which characterised Iranians as having a "bazaar mentality" that "often ignores longer-term interests in favour of immediately obtainable advantages," suggest that American diplomatic approaches were shaped by cultural stereotyping that may have undermined potential progress from the outset.

The practical consequence of these twin sources of distrust is a stance that renders meaningful negotiation extraordinarily difficult. Iranian officials maintain that conducting negotiations amid American threats, and without practical guarantees regarding the implementation of potential agreements, would effectively be engaging in a pointless exercise proposed merely to create an appearance of impartiality on the part of the United States. For meaningful dialogue to resume, Iranian officials have consistently maintained that manifested trustworthiness must precede engagement – a precondition that remains unmet in Tehran's assessment. This is not merely a rhetorical position; it reflects a strategic calculation that the costs of entering negotiations without credible assurances outweigh potential benefits.

Remarkably, leaked US diplomatic cables reveal that American negotiators were instructed to approach talks with Iranians with specific cultural assumptions that mirror Iranian suspicions. These cables advised that one "should never assume that his side of the issue will be recognised, let alone that it will be conceded to have merits," that "interlocking relationships of all aspects of an issue must be painstakingly, forcefully and repeatedly developed," and that negotiators "should insist on performance as the sine qua non at each stage of negotiations" because "statements of intention count for almost nothing."

Most tellingly, American diplomats were instructed that "cultivation of goodwill for goodwill's sake is a waste of effort" and to "be prepared for the threat of breakdown in negotiations at any given moment and not be cowed by the possibility." These internal directives, which characterised Iranian negotiators as having "cultural and psychological limitations," suggest that Washington's approach was fundamentally adversarial, presuming bad faith even with the former regime of the Shah even before discussions began – precisely the dynamic that Iranian officials have long suspected.

Documents like those contained in the CIA’s leaked Wikileaks have been picked through by Tehran dozens of times since their release, and any mutual stance creates significant obstacles to diplomatic progress despite periodic overtures from Washington, suggesting that without addressing the fundamental issue of trust – or creating mechanisms that function effectively even in its absence – the diplomatic impasse is likely to persist, regardless of the administration in Washington or the government in Tehran.