Iran's leadership is betting it can outlast an embattled US President Donald Trump in high-stakes negotiations, despite analysts warning this strategy relies on a volatile mix of brinkmanship, economic pain tolerance, and potential geopolitical miscalculation. With a fragile ceasefire holding nearly two-and-a-half months after a US-Israel war on Iran, tensions remain high, with Trump dismissing Tehran's settlement proposal as inadequate and warning the truce is "on massive life support." However, Iranian leaders appear convinced they can absorb pressure longer than the US can sustain confrontation.

Analysts note Iran's leadership believes that negotiating the best possible conditions is essential for their survival, making them willing to endure significant economic pain to outlast Trump. Sanam Vakil, from Chatham House, stated, "They do think they can outlast Trump. The war is existential for them." This perspective is reinforced by their belief that they have a "magic bullet" in controlling the Strait of Hormuz, the first time they have restricted shipping traffic through this key bottleneck for trade and energy supplies after years of threats. This control gives them significant leverage, with Thomas Juneau suggesting the "Hormuz lever is essential for Iran" and that Trump will lose patience due to higher oil prices as US midterms approach.

Despite this defiance, analysts caution that Iran's leadership is taking a gamble, facing a "hugely discontented population," a struggling economy, and major damage to civilian and military infrastructure from previous US-Israeli attacks. Maziar Khosravi, a journalist and political analyst, remarked that Trump and Israel can no longer effectively use the threat of military action to pressure the leadership. However, some analysts view Iran's approach as "delusional" and fear it could backfire, leading to a resumption of war, as the Trump administration may misunderstand the rigidity of Iran's leadership mindset.