Donald Trump has again left the door open to negotiations with Iran, raising the possibility that diplomacy could eventually reach the highest level — a direct meeting with Iran’s new Supreme Leader, Ayatollah Mojtaba Khamenei.

The idea is extraordinary because the war is deeply personal for Khamenei. His father, former Supreme Leader Ayatollah Ali Khamenei, was killed in the opening U.S.-Israeli strikes on Iran in February. Reports also said Mojtaba’s wife Zahra, one of his sons, a sister and other relatives were killed in the attack, while Mojtaba himself was wounded.

For Tehran, sitting across the table from the American president would therefore be far more than an ordinary diplomatic meeting. It would mean negotiating with the leader of the country that Iran holds partly responsible for killing members of the supreme leader’s own family.

So why would Iran even consider it?

The first answer is simple: states often negotiate with enemies they despise when the cost of continuing a conflict becomes greater than the political cost of talking.

Iran is under enormous pressure. The war, sanctions, disruption to oil exports and the confrontation over the Strait of Hormuz have all placed further strain on an economy already struggling with inflation and isolation. The Trump administration has also intensified its economic pressure on Tehran while continuing to insist that Iran cannot obtain a nuclear weapon.

That gives Iran a powerful reason to keep a diplomatic channel open, even if the leadership has little trust in Washington.

But there is an important distinction between talking and surrendering.

Mojtaba Khamenei has already shown that he is willing to permit direct negotiations with the United States under certain conditions. In June, he approved direct talks after an interim memorandum between Washington and Tehran, while publicly stressing that negotiations did not mean accepting the American position.

That is likely to remain the Iranian calculation: diplomacy can be used as another battlefield, not necessarily as an act of reconciliation.

What could Iran gain from talks?

For Tehran, a direct meeting could offer several potential advantages.

It could provide a route towards sanctions relief, the release of frozen Iranian assets, reduced military pressure and an agreement over shipping through the Strait of Hormuz. Iran has publicly demanded that Washington lift its blockade of Iranian ports, remove oil sanctions, release frozen assets and end military threats and operations.

A meeting could also allow Iran to press those demands directly at the highest political level rather than relying entirely on intermediaries.

There is another consideration: preventing another major escalation.

After months of strikes, threats, collapsed agreements and contradictory public statements, direct communication between the two sides could reduce the possibility that a misunderstanding or miscalculation triggers another round of large-scale fighting.

There is also a domestic political argument.

Iran’s leadership is facing competing pressures over how to deal with Washington. President Masoud Pezeshkian and other officials have pushed for negotiations to bring the conflict to an end, while harder-line elements have argued for maintaining military pressure and demanding greater concessions from the United States.

For Mojtaba Khamenei, agreeing to personally meet Trump would therefore carry enormous political risk.

Hardliners could portray the move as weakness, particularly after the deaths of his father and other members of his family. Any meeting would almost certainly have to be presented inside Iran as negotiations from a position of strength — not an attempt at friendship, reconciliation or surrender.

The symbolism would be enormous

Trump has previously said he would be willing to meet Mojtaba Khamenei if it helped produce a deal.

But the current diplomatic picture remains unstable.

On August 18, Trump said there were no U.S.-Iran talks taking place and none were scheduled. The following day, when asked when negotiations could resume, he said it might happen “at some point.”

So, despite talk of direct diplomacy, there is currently no confirmed Trump-Khamenei summit on the calendar.

But the possibility remains politically significant because both sides still have reasons to avoid an open-ended confrontation.

Iran wants economic breathing room, relief from sanctions and assurances against further attacks. Washington wants restrictions on Iran’s nuclear program, greater stability around the Strait of Hormuz and an agreement Trump can present as a successful outcome of his pressure campaign.

Those interests do not mean the two governments trust each other.

They do mean there is something to negotiate.

Could Khamenei really sit across from Trump?

The personal dimension makes any potential meeting unlike almost anything seen in modern U.S.-Iran relations.

If Mojtaba Khamenei were eventually to sit face-to-face with Trump, he would be meeting the American president after a war in which his father, wife, child, sister and other relatives were reportedly killed.

For many Iranians, seeing such a meeting could be extremely difficult to accept.

For Iran’s leadership, however, the final decision would ultimately be based on national power, regime survival and strategic advantage rather than personal emotion alone.

History is filled with governments negotiating with countries they had recently fought. Diplomacy between enemies is rarely built on trust or affection. Sometimes it begins because both sides decide the alternative is becoming too costly.

Iran may believe sitting down with Trump could win concessions that continued confrontation cannot. Washington may believe direct talks could force Tehran into commitments that military and economic pressure have so far failed to secure.

Neither calculation requires forgiveness.

The question is therefore not whether Tehran has reasons to reject Trump.

It clearly does.

The real question is whether Iran eventually decides it can gain more by sitting across the table from him than by continuing the confrontation.

And after everything Mojtaba Khamenei has personally lost, a face-to-face meeting would be one of the most extraordinary diplomatic encounters of the conflict.