Iran may learn the hard way that the days of Obama are gone

The real question is not whether negotiations will succeed or fail, but rather if Tehran will recognise that the rules of the game have changed

Iran may learn the hard way that the days of Obama are gone

In 2015, Iran signed the nuclear agreement under Barack Obama’s administration, which separated the nuclear file from missiles and regional influence and, in practice, accepted Iran’s strategic advance in return for nuclear restrictions. That agreement was the product of an exceptional moment: an American president willing to build legal arguments and pursue diplomatic compromises, a favourable international climate, and an Iran on the rise across the region.

The agreement did not last long. Trump took office in 2017, withdrew from the nuclear deal in 2018, imposed a campaign of maximum pressure, and ordered the assassination of Qasem Soleimani in 2020.

During Joe Biden’s presidency, Iran gambled in the 2022 Vienna talks on the assumption that the war in Ukraine would divide the West and heighten the need for alternative energy supplies to offset reduced Russian exports. It believed that this would strengthen its negotiating position and raise the value of its resources. It did not. By clinging to the remnants of the Obama approach, Iran squandered the chance of an agreement that could have eased sanctions.

During Trump’s second term, Tehran bet in June 2025 on the Muscat and Rome talks and on extending the 60-day deadline set by Trump. It sought to buy time and keep the files separate, as it had under the Obama administration, but Trump caught it off guard by bombing nuclear facilities. The negotiations and deadline were seen by many as a ruse.

Same story, bigger risks

Today, we see the same story repeating itself, but the risks are far greater. Trump’s message is clear: either an agreement that covers the nuclear issue, missiles, and Iran’s regional role within a limited timeframe, or military confrontation. An unprecedented military deployment in the region is already in place.

Institutional rigidity seems to be clouding Iran's better judgment. Confidence can breed complacency and lead to underestimating risk.

For its part, Tehran is betting on dragging out the process, while Washington wants quick capitulation.  And while Iran must surely understand that it is in a far weaker position after October 7 2023—when Israel severely weakened it, along with its proxies across the region—it is still working on outdated templates that may have once worked but no longer apply in this contemporary predicament.

Clouded judgment

Institutional rigidity seems to be clouding Iran's better judgment. Confidence can breed complacency and lead to underestimating risk. So the real question is not whether negotiations will succeed or fail, but rather if Iran will recognise that the rules of the game have changed.

In the past, Iran recognised when it was time to throw in the towel. In 1988, then-Supreme Leader Ayatollah Khomeini famously described accepting UN Resolution 598, which ended the 8-year Iran-Iraq War, as "drinking from a poisoned chalice"—a decision he deemed humiliating but necessary for regime survival. It also accepted the fall of Assad in December 2024 and cut its losses there, losing its only state ally in the region.

Iran faces a similar test today, but in a more complex setting and one less forgiving of miscalculation. In brinkmanship, wars rarely begin because the parties want them, but because each side is convinced the other will blink first. If Iran keeps negotiating as if this were 2015, it may learn the hard way that the days of Obama are long gone.

font change