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The One Dictator Trump Doesn’t Love

What’s different about Khamenei?

Benjamin Parker's avatar
Benjamin Parker
Jun 25, 2025
∙ Paid

Hey, everyone. I’m filling in for JVL today and we’re gonna talk about all the things you’re not supposed to discuss at the dinner table: religion, politics, and Donald Trump.

JVL will be back online tonight with Sarah and Tim for a special live edition of The Next Level. Set a reminder here. We’ll email a link as they go live and post the replay on the site when they are done.

Also, I’ve added a list of some of The Bulwark’s best Iran coverage below, so make sure to check that out!
–Ben


Iranian Supreme Leader Ayatollah Ali Khamenei (Composite by Hannah Yoest / Photos: Sobhan Farajvan/Pacific Press/LightRocket via Getty Images / Shutterstock)

There’s almost no dictator for whom Donald Trump doesn’t have kind words—from rapacious police-state thugs like Vladimir Putin, to aspiring hegemons like Xi Jinping, to monsters like Kim Jong-un, to minor-but-charismatic demagogues like Nayib Bukele, to run-of-the-mill autocrats like Abdel Fattah el Sisi, to ambitious murderers like Mohammed bin Salman.

There’s only one dictator anywhere for whom Trump has demonstrated nothing but hostility and contempt:

Grand Ayatollah Sayyid Ali Hosseini Khamenei, the supreme leader of Iran.1

What makes Khamenei different? He’s not more evil, more hostile to the United States, more abusive to his people at home, or more of an international menace than other dictators.

There are two possible explanations, and they’re not mutually exclusive. The first one is probably the right one. But the second one is probably the more interesting one.

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