President Donald Trump’s ongoing challenges in negotiating with Iran underscore a longstanding pattern of U.S. difficulty in engaging with the country’s complex political leadership, according to experts and historical precedent. Trump’s public frustrations, including recent remarks labeling Iran as “unbelievably duplicitous,” reflect his broader struggle to effectively navigate Tehran’s opaque power structures.

Since the 1979 Islamic Revolution, successive American presidents have sought to decode Iran’s political system, which blends elected institutions with overarching religious authority vested in the supreme leader. Most efforts have fallen short, with some encounters ending in setbacks. Experts note that Trump’s approach—oscillating between aggressive rhetoric and efforts at negotiation—has produced no substantial breakthroughs, despite occasional hopes for progress.

Trump’s handling of Iran intensified after the U.S. strike in February that killed Iran’s long-time supreme leader, Ali Khamenei. In the weeks that followed, Trump openly called for regime change and expressed readiness to select Iran’s next leader. Instead, Iran named Mojtaba Khamenei, the deceased leader’s son, to a prominent role. U.S. officials regard him as more hardline and nuclear ambitions as likely to increase under his influence. Tehran has rejected overtures that do not align with its core interests, including Trump’s insistence on halting Iran’s collection of fees in the strategic Strait of Hormuz, a vital artery for global oil shipments.

Despite public walkbacks and revised assessments, Trump continues to voice hopes for a deal that could normalize Iran’s international standing. Iranian officials, however, maintain they are open only to limited negotiations, such as those concerning the Strait of Hormuz and nuclear issues, while ruling out broader reconciliation with the United States, which remains widely viewed within Iran’s political establishment as an adversary.

This dynamic highlights a broader challenge pointed out by longtime observers: the U.S. has consistently underestimated the entrenched ideological commitments of Iran’s ruling elite and the institutional power held by religious and military leaders. Suzanne Maloney, a foreign policy specialist, notes that the war has further consolidated the influence of Iran’s hardline factions, leaving few internal alternatives for a shift in policy.

Historical parallels reinforce this persistent difficulty. From President Jimmy Carter’s failed hostage negotiations in 1980 to President Ronald Reagan’s covert arms sales during the Iran-Contra affair, U.S. attempts to engage Iran have often encountered unexpected resistance or backlash. President Bill Clinton saw a brief opening with reformist President Mohammad Khatami in the late 1990s, which included gestures toward improved relations, but this was ultimately undercut by hardline opposition within Iran’s hierarchy. Similarly, President Barack Obama’s 2015 nuclear agreement, negotiated with moderate Iranian leadership, marked a rare diplomatic achievement but failed to yield broader rapprochement, as Tehran’s supreme leader remained opposed to major political change with Washington.

Since Trump withdrew from the 2015 deal in 2018 and reinstated sweeping sanctions, Iran has accelerated its nuclear activities, raising tensions that culminated in the recent military confrontations. Analysts emphasize that Tehran’s calculated patience has often outmaneuvered U.S. urgency, with Iranian leaders operating from a long-term perspective that views time and endurance as strategic advantages.

As the United States continues to grapple with Iran’s multifaceted leadership and strategic priorities, the pattern of misreading and miscalculation appears unlikely to change in the near term, according to multiple assessments from seasoned diplomats and regional experts.