For years, Donald Trump and his supporters often said that Iran never wins wars, but never loses negotiations either. This critique was often made about U.S. administrations, particularly the Obama administration and the 2015 nuclear deal, which Trump called one of the worst agreements in American history. However, under Trump’s leadership, recent events suggest a different, even ironic, outcome. It seems Trump has lost both the military confrontation with Iran and the negotiations that followed.
By disrupting maritime traffic and amplifying fears of a prolonged energy shock, Iran demonstrated the economic costs of ongoing escalation.
The February 2026 U.S. intervention and the negotiations that followed produced a very different result. Although Washington entered the confrontation with overwhelming military superiority and ambitious objectives, it ultimately failed to achieve its central political goals—largely due to incompetence in political leadership and a lack of true understanding of the Islamic Republic. The United States was unable to compel the Islamic Republic to fundamentally change its ideological identity, regional posture, or strategic orientation. Instead, Tehran leveraged one of its few remaining sources of influence—its ability to disrupt the global economy by closing the Strait of Hormuz. By disrupting maritime traffic and amplifying fears of a prolonged energy shock, Iran demonstrated the economic costs of ongoing escalation. As oil and gas markets responded, pressure grew on Washington to find a quick resolution to the crisis, as even President Trump noted.
The outcome seems to be a memorandum of understanding giving Tehran many concessions at the expense of some limited structural changes. The reports about easing sanctions, economic opportunities, and exemption periods show a degree of flexibility that would not have been politically possible in previous periods of Trump’s Iran policy. For instance, Iranian sources claim that the negotiation team arrived at an agreement in Switzerland regarding the release of $12 billion in frozen Iranian assets. If these reports turn out to be true, the administration that called any negotiations with Iran appeasement would have entered into an agreement in which Iran receives considerable economic gains without making any behavioral or ideological changes to the regime. So far, the main thing that Tehran has agreed to do is open the Strait of Hormuz, which was open before Trump started attacking Iran.
Trump and Vice President J.D. Vance are both touting the deal as a diplomatic victory, although the long-term ramifications may be quite the opposite. Sanctions relief and renewed access to foreign investment would give the Islamic Republic resources at a time when its military credibility and regional influence have been severely hurt. But there is little evidence that the regime has abandoned its core objectives. Rather, Tehran appears to be pursuing what late Supreme Leader Ali Khamenei has long described as “heroic flexibility”—a tactical adjustment designed to preserve the regime, reduce immediate pressure, and create favorable conditions for future recovery.
While military force can erode capabilities, devastate facilities, and impose costs, it cannot easily force ideological transformation in a regime such as the Islamic Republic.
At the same time, the United States faced constraints of its own, since escalation threatened energy markets, regional stability, and the broader global economy. Rising economic costs increased pressure on Washington to seek a negotiated exit from the crisis; it did so. As the risks of prolonged conflict mounted, the administration’s bargaining position weakened. The result was a familiar paradox: the stronger military power found itself making concessions to stabilize the very situation it had sought to control.
This outcome of the U.S.-Iran conflict will carry a broader lesson about coercive diplomacy; most critically, that the assumption that military pressure automatically produces political surrender is flawed. This is especially true when it is done by an incompetent administration, which alienated its allies and was not able to create a global alliance. It is even more true when dealing with revolutionary regimes. The Islamic Republic’s leadership has consistently demonstrated a willingness to absorb extraordinary costs in pursuit of regime survival. Military action can influence Tehran’s calculations, but it cannot by itself resolve the underlying political conflict between Washington and Tehran.
For Trump, the political implications are especially significant. His critique of the Obama administration rested on the argument that American negotiators traded sanctions relief for inadequate concessions. Yet the emerging agreement may expose him to the very same criticism. If Tehran retains its essential political and strategic characteristics while receiving substantial economic benefits, critics will rightly argue that the administration accepted a deal even less favorable than the one it spent years condemning.
Military action can influence Tehran’s calculations, but it cannot by itself resolve the underlying political conflict between Washington and Tehran.
Published originally on June 25, 2026, under the title “Trump Lost Both the War and the Negotiation.”
