It was just past sunset on Feb. 21, 2022, when Russian President Vladimir Putin began his infamous speech effectively declaring war on Ukraine. I was in a hotel in Vienna that evening, and all indications suggested that Iran, the United States, and the remaining parties to nuclear negotiations were hours away from announcing an agreement. European Union coordinators told me as much, as did members of the Iranian negotiating delegation.
Then, the war in Ukraine began. The agreement never materialized. Advisors close to the Iranian delegation quickly concluded that the world after the Russia-Ukraine war would no longer resemble the one before it. That assessment was relayed to Tehran’s leadership. One phrase circulated repeatedly among Iranian officials: “Winter is coming,” borrowed from Game of Thrones. The expectation was clear: Europe would face a severe energy crisis, Western unity would fracture, and Iran’s bargaining position would improve.
It was just past sunset on Feb. 21, 2022, when Russian President Vladimir Putin began his infamous speech effectively declaring war on Ukraine. I was in a hotel in Vienna that evening, and all indications suggested that Iran, the United States, and the remaining parties to nuclear negotiations were hours away from announcing an agreement. European Union coordinators told me as much, as did members of the Iranian negotiating delegation.
Then, the war in Ukraine began. The agreement never materialized. Advisors close to the Iranian delegation quickly concluded that the world after the Russia-Ukraine war would no longer resemble the one before it. That assessment was relayed to Tehran’s leadership. One phrase circulated repeatedly among Iranian officials: “Winter is coming,” borrowed from Game of Thrones. The expectation was clear: Europe would face a severe energy crisis, Western unity would fracture, and Iran’s bargaining position would improve.
Winter came and went. The bet failed. Tehran’s wishful assessment deprived it of an agreement that could have partially eased sanctions during then-U.S. President Joe Biden’s time in office. Iran’s strategic sensors either failed or functioned exactly as programmed, reinforcing expectations rather than challenging them.
This failure of judgment now appears less like an isolated episode and more like a recurring pattern, one that has resurfaced at a far more dangerous moment.
Officials involved in the current diplomatic track have underscored a widening mismatch between how Tehran understands negotiations and how Washington now conducts them. One regional diplomat involved in mediation described what he called a growing “velocity gap.” Regional intervention, he said, was the only reason that war had not erupted weeks earlier. His concern was not simply disagreement between the parties but a fundamental misreading of time itself. “This is not a traditional American administration operating according to familiar institutional rhythms,” he said. “Trump is looking for quick, visible victories. Patience is not his strategic instinct.”
The diplomat’s message was blunt: If Tehran believes that it can prolong negotiations toward U.S. midterm elections to gain leverage, then that would be a serious miscalculation. Washington’s tolerance for delay may expire long before any diplomatic timeline that Tehran considers realistic. The diplomat’s warning echoes earlier moments when Iranian strategic expectations collided with unfolding reality.
On the eve of Israel’s war against Iran last June, Iranian officials assessed, based on diplomatic signals, that Israel would not strike before the sixth round of negotiations in Muscat concluded. Military planners believed that any attack would focus narrowly on nuclear facilities rather than Tehran itself.
Instead, Iran’s capital awoke before dawn to coordinated airstrikes and internal drone operations that eliminated much of the country’s senior military leadership. The war lasted 12 days, and U.S. President Donald Trump authorized direct U.S. strikes on Iranian nuclear facilities toward the end of it.
Perhaps the most striking revelation came afterward: Iranian officials acknowledged that enriched uranium at the 60 percent level had not been moved out of nuclear sites beforehand. Tehran had not anticipated U.S. entry into the war. But Washington entered, nonetheless.
When the conflict ended with a cease-fire, following what Tehran described as a largely symbolic strike on Al Udeid Air Base in Qatar, Iranian officials assumed that negotiations could resume under familiar terms. But the reality had fundamentally changed. The war had occurred, disabling key infrastructure and reducing enrichment to effectively zero. Iran’s bargaining leverage, nuclear and regional alike, was significantly weakened.
And yet, Tehran still behaved as though the previous negotiating framework remained intact. A former Iranian official offered a candid explanation during a conversation shortly after the war. The problem, he argued, was not ignorance but institutional inertia. “The establishment here is stuck with the 2015 model,” he said. “But the way the stars aligned in 2015 was unprecedented. It cannot be repeated.”
The 2015 agreement, known as the Joint Comprehensive Plan of Action, emerged from a rare convergence: political willingness in Washington, strategic flexibility in Tehran, and an international environment conducive to compromise. None of those conditions exist today. Now, with Washington insisting that ballistic missiles and regional activity be addressed alongside nuclear restrictions, the old negotiating toolkit has become largely obsolete. From this perspective, Tehran is attempting to fight a new strategic confrontation using assumptions shaped by a different era.
This helps explain why Iranian decision-makers continue to interpret mounting U.S. military deployments, including the arrival of a second aircraft carrier, primarily as pressure designed to force negotiations rather than preparation for escalation. The dominant belief remains that Washington ultimately seeks a nuclear agreement and wants to avoid a prolonged regional war.
The problem is not a lack of preparation for conflict. Iran is showcasing its capabilities, and according to Western reports, restocking its arsenal. The problem is Iran’s confidence in a familiar diplomatic ending.
Geopolitically, the environment surrounding Iran has transformed. Syria has completely fallen out of Iran’s strategic equation following the collapse of Bashar al-Assad’s government. Hezbollah and Hamas lost much of their defensive capacity during the 2023-2024 war with Israel. Iraq is recalibrating and distancing itself from regional confrontation.
In short, the Middle East that shaped Iran’s deterrence doctrine before the Israel-Hamas war no longer exists. Yet Iran continues to negotiate as though it does.
Even after Israeli Prime Minister Benjamin Netanyahu’s meetings with Trump in Washington, discussions led by Iranian National Security Council Secretary Ali Larijani in Muscat and Doha remained confined largely to the nuclear file. Iranian officials appear unconvinced that Trump is willing to sustain a conflict capable of paralyzing the region through prolonged missile exchanges.
It’s a classic gamble, and it applies to both the United States and Iran, assuming that turning up the heat is just a way to get what they want, not a plan to burn the whole house down. But the real danger of playing chicken isn’t about what they meant to do; it’s about whether they wait too long to swerve. Sometimes, the clock runs out before “leverage” has a chance to work.
Inside Iran, war is discussed through an unusually revealing sequence: first, the exchange rate, then geopolitics. One segment remains ideologically committed, viewing dissent through the lens of external confrontation and interpreting domestic struggle as part of a sacred defensive mission tied to religious doctrine. Another seeks stability above all else, criticizing governance while fearing national fragmentation more than authoritarian continuity.
A smaller but increasingly audible segment, particularly among younger Iranians, views war itself as a potential rupture that could end what it describes as a slow national decline. During interviews in Tehran, some expressed the belief that external strikes might target institutions rather than civilians and open the door to a radically different political order. Clearly, they are too young to have witnessed the invasion of Iraq in 2003 and its aftermath.
Washington continues to escalate pressure, while Tehran remains convinced that negotiations will ultimately resolve the crisis. Yet U.S. demands now challenge a core pillar of Iran’s defensive doctrine: its ballistic missile program. Accepting such conditions could leave Iran strategically exposed. Rejecting them risks confrontation.
Confidence, paradoxically, may be Iran’s greatest vulnerability. The events of June 2025 transformed what once seemed unthinkable into a plausible strategic opening for Washington and its allies. Sustained pressure may aim less at overthrowing the regime than at reshaping its trajectory through exhaustion and internal strain. Whether such a strategy can succeed remains uncertain. Iran’s multilayered political system is designed precisely to resist sudden transformation.
For now, Tehran remains convinced that the negotiating table will produce a solution. Perhaps it will. But the danger lies in a shared assumption guiding both capitals: that the other side will blink first. And in brinkmanship, wars rarely begin because they are desired, but rather because each side believes it understands the other too well.
