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Reading the enemy

A veteran Mideast diplomat on meeting Khamenei, Iran's war strategy and where the region may be headed

Ambassador Jeffrey Feltman is one of the few Americans ever to have met Iran’s late Supreme Leader Ayatollah Ali Khamenei - a surreal encounter he experienced as a top UN diplomat accompanying Secretary-General Ban Ki-moon to Tehran in 2012. As he told us in our conversation, he was struck by how little Khamenei actually understood about the United States. America’s picture of Iran may have its gaps, but Khamenei, Feltman said, described a caricature of the country - a portrait that bore little resemblance to the Great Satan his regime had spent half a century railing against. He wrote about the experience at length for Brookings, where he is currently a visiting fellow, and it’s well worth a read.

What also struck him was Khamenei’s utter ack of charisma. That stood in sharp contrast to Hassan Nasrallah, the longtime Hezbollah leader whose commanding personality had frustrated Feltman during his years as US Ambassador to Lebanon. Nasrallah was killed in an Israeli airstrike in Beirut in September 2024 - ending a 32-year reign at the helm of one of the region’s most powerful armed movements.

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Few people understand the Middle East’s fault lines - and America’s complicated role within them - quite like Jeff, who has spent decades navigating the region’s most volatile moments from the inside. In our conversation, he shared his unvarnished read on the current war, Iran’s strategic calculus, and what kind of Middle East may emerge on the other side.

Jeff - who oversaw the largest non-combatant evacuation in US history during the 2006 Lebanon war - had little patience for the Trump administration’s failure to evacuate Americans before this war began, calling it a flat-out “dereliction” of duty.

If you missed the live interview, the recording is below. It runs a bit longer than usual, because Jeff had that much to say, and frankly, we could have kept going.

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Danielle Pletka and I are back in business later today with Hot Takes Happy Hour. Much to discuss. Hope to see you at 5:30p ET. Same bat channel, same old bats. 🦇🦇

Thank you Marcie Alexander, Edward F Dijeau, Janice Driver, Renée, Rick, and many others for tuning into my live video with Jeffrey Feltman! Join me for my next live video in the app.

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