President Donald Trump Upends Expectations In Meeting Iranian Supreme Leader.

Washington DC; June 2026: US President Donald Trump have upended expectations yet again when he told reporters on Friday (05th June 2026) that he would be “honoured” to meet Iran’s Supreme Leader in the event of a peace deal. “If we make a deal, it’s possible that I would meet him”, the US president have said in the Oval Office.

The idea of a meeting between Trump and Mojtaba Khamenei anytime soon borders on inconceivable.
That’s not only because of the death, damage and bitterness caused by the war the US and Israel launched against Iran on February 28th. It’s also because of the specific toll exacted upon Khamenei’s family.

The current supreme leader ascended to the position after his father, Ayatollah Ali Khamenei, was killed in an Israeli air strike on the first day of the war (28th February 2026), alongside Mojtaba Khamenei’s wife and one of his children were also reported to have been killed.

When asked by press reporters, whether this might mean that Khamenei has “hard feelings and wouldn’t want to meet”, Trump replied: “Well, I would say I’m not his favourite person. But, with that being said; he’s probably a professional. In some circles, he has a very good reputation, actually”.

The shockwaves were immediate across the foreign policy world. “I saw that comment and my first thought was, ‘My God, does he know what they think of him?’” said Joel Rubin, who served as a deputy assistant secretary of State during the administration of former President Obama.

But while the notion of a meeting between the American president and the Iranian supreme leader seems shocking to critics, it is consistent with other instances where Trump has been willing to sit down with enemies or adversaries prior presidents would have avoided entirely, or at least treated with extreme wariness.

The most prominent example came during Trump’s first term in relation to North Korea. Having once disparaged Kim Jong Un as “Little Rocket Man” and threatened his nation with “fire and fury”, Trump later became the first president to meet any North Korean leader. He met Kim thrice. During his third meeting, held at the demilitarised zone between North Korea and South Korea, Trump marked another presidential first when he set foot on the northern side of the border.

If other meetings weren’t quite so startling as that one, Trump’s recent trip to China to meet President Xi Jinping was clearly a significant event. So too was his Alaska summit with Russian President Vladimir Putin on 15th August 2025.

Trump clearly enjoys the spectacle of such encounters and the degree of which they spark media fervour. But his critics question whether any real achievements spring from them. The summit with Putin, in particular, faced criticism because of the way it allowed the Russian president to savour the pomp and ceremony while making virtually no meaningful concessions.

Senator Chris Murphy (Democrat-Connecticut) at the time contended that Putin had “got everything he wanted”.

Such jabs, in turn, spurred Trump to hit back. “Murphy is a lightweight who thinks it made the Russian President look good in coming to America. Actually, it was very hard for President Putin to do so. This war can be ended, NOW, but stupid people like Chris Murphy, John Bolton, and others, make it much harder to do so”, Trump contended.

Similarly, the more recent summit with Xi failed to produce any public commitment from Beijing to lean on Iran to open the vital Strait of Hormuz. The Chinese side also issued an ominous warning that the issue of Taiwan would have to be dealt with “properly” or risk “clashes and even conflicts”. Still, Trump called the trip “incredible”, emphasising trade deals.

To be sure, Trump’s propensity to breach norms in diplomatic matters can take an aggressive shape as easily as a more affable one. Most notably, his frustration at a fraying ceasefire between Iran and Israel back in June 2025 boiled over when he told reporters at the White House that the two nations “don’t know what the blunder they’re doing”.

Last week, Trump confirmed reports of another profane phone call with Israeli Prime Minister Benjamin Netanyahu, this time over continuing Israeli attacks on Lebanon.

Independent observers say that Trump is clearly willing to take risks that presidents who operate within more normal parameters are not. The question is whether the risks commensurate rewards.

“To the extent that there is an upside, it is that he is willing to take a risk that goes against the small-c conservative approach, because he doesn’t care about the normal protocol”, said Grant Reeher, a professor of political science at Syracuse University. “He is always looking to surprise people and to go against type. The problem is, he sometimes does that in ways we all wish he didn’t”.

Rubin, the former State Department official and the author of a recent book titled, “Saving Democratic Foreign Policy: How Democrats Can Earn the American People’s Trust to Lead the World Once Again”, contended that the more traditional standards of diplomacy have a real value, one which Trump skates past.

“I’m a big advocate for diplomacy but not for reckless diplomacy”, Rubin said. “He believes you just go meet, and you fix it, and it’s completely devoid of context”. Reeher offered a somewhat more forgiving explanation for Trump’s apparent willingness to meet with Khamenei.

“He tends to think in terms of transactions, and he thinks of it as ‘Would you be willing to meet this person?’ He doesn’t think about it in terms of ‘the leadership of Iran’ or the nature of Iran. He thinks, ‘I can have a productive meeting with any person’”.

If that is what Trump thinks, it may be a long time before the world finds out if he is correct.

Yesterday (Friday, 05th June) Mohsen Rezaei, a military adviser to Khamenei, adamantly poured cold water on the idea of such a meeting. “This will not happen”, Rezaei told media reporters. “Right now, we are in the first stage of negotiations and Mr. Trump has brought the negotiations to a standstill. This will not happen”.

Team Maverick.