When Donald Trump withdrew the United States from the Joint Comprehensive Plan of Action—otherwise known as the Iran nuclear agreement—in 2018, he declared that his predecessor had signed “the worst deal in history” and promised to do dramatically better. It was a characteristically bold claim—and one that has since metastasized into a strategic trap from which his administration cannot escape. The withdrawal did not simply set the United States and Iran on a collision course realized years later. It established a political baseline that now constrains Trump’s ability to negotiate any agreement at all, because any deal resembling what already existed will be indistinguishable, in the eyes of his critics and his base alike, from defeat.
The logic of Trump’s first-term approach was coherent, if ultimately self-defeating. Maximum pressure sanctions were designed to bring Iran to its knees economically and deliver a more pliable negotiating partner. The assassination of senior Iranian military figures like Qassem Soleimani was intended to sharpen that pressure. What this calculus missed was Tehran’s internal politics. Rather than empowering the pragmatists who had staked their credibility on engagement with the West, Trump’s campaign vindicated the hardliners by demonstrating that accommodation with America not only failed to pay dividends, but it invited further pressure.
Iran’s response to the Trump administration was delivered regionally. To break Washington’s containment architecture, Tehran orchestrated calibrated strikes against the Gulf states that had been cheerleading the maximum pressure campaign. The message was received clearly in Riyadh and Abu Dhabi. Those capitals, recognizing that the U.S. would not reliably defend them in a direct confrontation with Iran, moved bilaterally to defuse tensions by restoring relations and presenting themselves as neutral parties.
When Trump returned to office in January 2025, the regional landscape had shifted dramatically. The regional military conflict that had begun in October 2023 had significantly degraded Iran’s alliance network and left the regime exposed. With the wind at his back, Israeli Prime Minister Benjamin Netanyahu persuaded Trump that the moment was ripe for decisive military action. In June 2025, amid U.S.-Iran negotiations, Israel launched a 12-day aerial campaign, which the U.S. joined in its final phase with a massive strike on Iran’s nuclear program. Tehran’s response—launching a symbolic strike on a single U.S. military base—was restrained enough to be misread in both capitals as a sign of vulnerability rather than strategic caution.
That misreading proved catastrophic. When Tehran again refused to capitulate at the negotiation table, the U.S. and Israel escalated with the current joint military assault at the end of February. The bet was that overwhelming force would topple the regime or compel Iranian submission. It has done neither, and instead backfired spectacularly by unleashing Iran’s military on the region and fundamentally transforming its leverage.
Before the war, Iran’s principal negotiating asset was the scope of its nuclear enrichment program. That asset has now been eclipsed. By seizing effective control of the Strait of Hormuz and holding global energy markets hostage, Iran has acquired a coercive instrument of extraordinary power—something it never possessed during the years of peacetime diplomacy. Simultaneously, the war has largely depleted America’s most valuable negotiating leverage: the credible threat of force. Despite suffering massive devastation, Iran has not only withstood the joint assault but achieved escalation deterrence on the battlefield, exposing the limits of American military power. The two sides now return to the negotiating table with Iran holding new, earned leverage, and the U.S. saddled with the growing costs of a war that has not delivered its objectives.
The result of this emerging power dynamic is an impasse. Trump wants out of the war—that much is evident — but he has no coherent plan for ending it, and no plausible path to an agreement objectively superior to the JCPOA he repudiated. To make matters worse, Trump has systematically hollowed out the agencies and career bureaucracies that would ordinarily provide the analytical depth and diplomatic continuity that complex negotiations demand. In their place, he relies on a tight circle of personal loyalists, like son-in-law Jared Kushner and real estate developer friend Steve Witkoff, who do not possess relevant experience or subject-matter expertise. Closing a nuclear deal with the Islamic Republic of Iran is not, it turns out, analogous to closing a real estate transaction on an office building in New York or a casino on the Jersey Shore. It requires institutional memory, technical mastery, and the ability to construct verification architectures of considerable complexity—none of which the current team can credibly supply.
The problem runs deeper still. Agreements are ultimately about compliance. They are only as good as the commitments underpinning them and the track records of those who made them. Trump’s record is damning. Critics of the 2018 withdrawal warned that it would severely corrode American credibility. Since then, this administration has used nuclear negotiations as diplomatic cover while military options were developed and executed. It has ordered the assassinations of Iran’s top leadership, including Supreme Leader Ali Khamenei, at the outset of the current war, the psychological impact of which cannot be downplayed.
The damage is not simply reputational. It has direct structural implications for any prospective agreement. If Washington cannot be relied upon to negotiate in good faith or honor its commitments, any deal must be underwritten by enforcement mechanisms that compensate—more elaborate verification regimes, more demanding compliance architecture—which require longer and more technically intensive negotiations.
The JCPOA was designed primarily to ensure Iranian compliance, with rigorous monitoring and snapback provisions to that end. This time, Iran is demanding compliance mechanisms for the United States, yet no framework exists to provide them. The old P5+1 structure lacks the standing to hold Washington—let alone Israel—to account. Designing something that ensures compliance on both sides requires a more robust agreement than the world has yet seen. That is why ceasefire negotiations have stalled. And it is why even a genuinely attractive offer from Washington is received in Tehran with warranted suspicion.
Meanwhile, the Trump administration has outsourced the heavy diplomatic lifting to Pakistan and other intermediaries. The president is now waiting on pins and needles and responding in real time—through social media and other channels—to every piece of information that reaches him, which explains the erratic public signaling that has characterized his approach since the war’s opening weeks. His evident puzzlement at Iranian decision-making reflects less Tehran’s political fragmentation—as Trump believes—than the absence of direct communication and the unreliability of filtered information.
The final wrinkle is that overlaying all these structural constraints to a deal is the domestic political constraint. Any agreement resembling the JCPOA will be presented by opponents as proof that the entire enterprise was a costly exercise in political gamesmanship that ended where it began, or somewhere worse. The anti-war left wants to punish Trump and the Republicans politically. The anti-war right wants the episode to serve as a cautionary tale about military adventurism. And the pro-war camp wants the fight to continue until real results are achieved, no matter the cost. Trump is caught between these forces, with no exit that satisfies any of them and therefore supreme difficulty in selling this war as a victory. To make matters more complicated, neither Israel nor the Gulf states wants a bilateral agreement struck over their heads that sacrifices their interests to Iran, and their capacity to complicate or delay a settlement cannot be discounted.
Amid this stalemate, the escalation trap beckons, offering the slim promise that applying more force can alter the equation in Trump’s favor. The most likely outcome under these conditions, however, is not a deal. It is prolonged stasis with no renewed fighting, no resolution, and a slow-motion American withdrawal from the strategic contest over the Strait of Hormuz—leaving other nations to negotiate their own passage arrangements with Tehran.
Trump’s predicament is no longer merely a policy failure. It is a strategic trap from which there may be no politically acceptable exit. The administration destroyed the original nuclear agreement, escalated toward war when coercion failed, and now confronts a negotiating environment in which Iran possesses more leverage and Washington less credibility than before the crisis began. Any realistic settlement risks resembling the very deal Trump once denounced as intolerable. But after years of maximalist rhetoric and military escalation, acknowledging that reality may itself be politically impossible.
