As the United States enters another potential phase of engagement with the Islamic Republic over its nuclear program and other critical issues, the course of action under President-elect Donald Trump remains uncertain. Whether he opts for negotiations or a different approach entirely, the stakes are undeniably high. Renewed diplomacy raises profound questions about its strategic feasibility and potential repercussions. The Trump administration faces a geopolitical landscape marked by entrenched ideological divides, shifting alliances, and the lingering impact of past U.S. administrations, including the disastrous appeasement attempts during President Joe Biden’s tenure to revive the Joint Comprehensive Plan of Action (JCPOA). Reflecting on these experiences and the manipulative tactics of the Islamic Republic’s leadership, this article examines why a new attempt at negotiations may fail and risks damaging Trump’s personal reputation while exploring alternative strategic considerations.

The Islamic Republic’s Ideological Constraints on Negotiation
Expecting the Islamic Republic to engage in meaningful negotiation is like asking a fish to climb a tree. Their worldview fundamentally opposes negotiation as a means to solve disputes. Rooted in an uncompromising narrative of resistance against perceived external oppression, their foreign policy aims not at compromise but at enforcing their vision of divine justice, which leaves no room for traditional diplomacy. The ultimate goal of the Islamic Republic’s leadership—to implement the rule of Allah globally—fuels their ideological rigidity. Negotiation, as understood by the West, is not a skill valued or available within their operational framework.

This rigidity is amplified in dealings with the United States, which the Islamic Republic frames as the archetypal oppressor. Manipulative tactics like the "good cop, bad cop" routine—frequently employed by figures such as Mohammad Javad Zarif—further highlight the futility of expecting substantive outcomes from such interactions. Israel’s security apparatus has repeatedly highlighted this strategy, underscoring that the Islamic Republic’s endgame is not reconciliation but the advancement of its ideological and nuclear ambitions.

Lessons from the Biden Administration’s Disastrous JCPOA Revival Attempt
The Biden administration’s appeasement-driven approach to reviving the JCPOA underscores the pitfalls of engaging with the Islamic Republic. Despite initial optimism, the strategy collapsed under its own contradictions:

1. Failing to Recognize the JCPOA’s Demise: The JCPOA was effectively a dead letter by the end of the Obama administration. Trump’s public declaration of withdrawing from the deal merely acknowledged this reality. Any successor — Republican or Democrat — would have faced the task of managing the deal’s failure. Biden’s decision to pursue revival efforts ignored this fundamental truth and only exposed his administration to further setbacks.
2. Miserable Failures of Appeasement: Biden’s “A Team” strategy was anything but, proving to be a recipe for failure. The administration’s concessions—including reduced economic pressure on the Islamic Republic—enabled their leaders to redirect funds toward hostile activities, potentially endangering U.S. personnel and interests. Unlike Trump’s decisive responses to threats against Americans, Biden’s hesitancy undermined U.S. credibility.
3. Ignoring Ideological Realities: Biden’s team seemed to operate under the delusion that the Islamic Republic’s leadership could be persuaded to change. This failure to acknowledge their ideological rigidity and manipulative tactics doomed the negotiations from the outset.
4. A Regional Domino Effect: Reduced pressure on the Islamic Republic emboldened its proxies and allies across the Middle East, destabilizing the region further and straining alliances forged under the Abraham Accords. Israel’s proactive measures against Iranian proxies like Hamas and Hezbollah illustrate the necessity of maintaining pressure.

Challenges Ahead for the Trump Administration
If President Trump opts to re-engage with the Islamic Republic—even on a limited basis, as suggested by “Richard Nephew’s” Richard Nephew’s "last-chance diplomacy" proposal—his administration must contend with significant challenges:

1. Ideological Intransigence: The Islamic Republic’s leadership perceives negotiations as a tactic for powerful adversaries to impose their will. This perception—rooted in their theological framework—renders genuine dialogue impossible. Any overture by the U.S. will likely be exploited by the Mullahs as an opportunity to buy time while advancing their strategic objectives, including achieving nuclear bomb capability amongst other hostile goals. Negotiation, as a tool, is simply not available to them or is not in their toolbox.
2. Domestic Political Constraints: Domestically, Trump faces a politically charged environment. Renewed engagement with the Islamic Republic risks alienating key segments of his political base while providing ammunition to critics who view his foreign policy as inconsistent. Any failure could undermine Trump’s image as a dealmaker—a reputation he has cultivated as a cornerstone of his leadership.
3. Shifting Regional Dynamics: The Middle East’s alliances have evolved significantly. The Islamic Republic’s partnerships with China and Russia offer it leverage but are not as robust as Tehran might hope. These relationships serve more as tools for Beijing and Moscow to counter the West than as strategic partnerships. Meanwhile, the Abraham Accords have strengthened the bloc of regional actors countering the Islamic Republic. Israel, in particular, remains a decisive force, pursuing actions that weaken Tehran’s proxies, such as Hamas and Hezbollah, while shaping the regional response to any U.S. engagement with the Islamic Republic.
4. Pressure vs. Diplomacy: The "maximum pressure" campaign imposed substantial economic costs on the Islamic Republic but failed to achieve comprehensive objectives. A purely pressure-based approach risks further entrenching hostility, while a sudden pivot to diplomacy undermines credibility. Addressing these challenges requires additional measures and creative tools, particularly as critical deadlines, such as October 2025’s sanctions sunset, loom large. Mechanisms like the snapback provision could provide leverage but require careful implementation.
5. Managing Reputational Risks: Engaging the Islamic Republic entails significant reputational risks for Trump. Failed negotiations could reinforce perceptions of inconsistency or impulsiveness, while perceived concessions might erode his image as a strong leader. The Mullahs’ predictable exploitation of U.S. missteps to bolster their domestic and international standing only heightens these risks. Recognizing the inherent limitations of negotiations and preparing for alternative strategies—akin to acknowledging the impossibility of teaching a fish to climb a tree—will be critical.

Conclusion: Navigating a Rocky Road
Engagement with the Islamic Republic remains a high-stakes venture fraught with ideological, political, and geopolitical complexities. The lessons from Biden’s appeasement failures illustrate the challenges of diplomacy with the Mullahs, while the Islamic Republic’s manipulative tactics continue to undermine any credibility in negotiations.

For Trump, the path forward demands a realistic and clear-eyed assessment of diplomacy’s limitations. By learning from past missteps and leveraging broader geopolitical dynamics, his administration can navigate the intricate U.S.-Islamic Republic relationship with greater strategic clarity. Ultimately, the stakes are both diplomatic and deeply personal, as Trump’s reputation as a leader capable of decisive action hangs in the balance. In doing so, time remains the single biggest challenge and enemy for Trump’s administration, requiring swift yet calculated moves to maintain leverage and protect U.S. interests.

Mehran Mossadegh is an expert negotiator and strategic thinker, the founder of NegotiationWise and has written further on the P5+1 and Iran negotiations below. He holds a masters in commercial law from Monash University and a bachelor of Engineering from University of Technology, Sydney.