John Heilemann: Did Trump Make an Ominous Shift on Iran?

In this episode of The Bulwark Podcast, host Tim Miller welcomes back chief political columnist at Puck and frequent analyst John Heilemann to discuss Donald Trump's increasingly authoritarian tendencies, particularly his decision to place his face on U.S. passports—a move Heilemann frames as part of a broader pattern of cult-of-personality cultivation reminiscent of Middle Eastern autocrats. The conversation shifts to the absurdity of the FBI's indictment of James Comey over a beach photo with seashells labeled '8647'—a metaphorical phrase meaning 'remove from the menu'—which Heilemann calls a transparent political weaponization of the DOJ. He argues that the timing of the indictment (after nine months) and the lack of any real investigation expose the farce, serving more to sustain the narrative of constant presidential threat than to address actual danger. The discussion then turns to the broader chilling effect on media and corporate America, where streaming giants like Netflix, Amazon, and Apple are avoiding politically sensitive content out of fear of Trump’s retribution, despite YouTube’s growth fueled by unfiltered political discourse. Heilemann warns that Trump’s Iran policy has backfired strategically, strengthening Iran’s regional power while failing to deliver any meaningful win, and that the war’s economic fallout—rising gas prices, supply chain disruptions, and $25 billion spent—is now locked in. He concludes with a sobering assessment: Trump’s political standing is in irreversible decline, with no clear path to recovery, and the Democratic Party may be poised for a wave not because of polling, but due to real electoral performance in recent races. The episode ends with a rapid-fire exchange on the future of American democracy and a playful debate over the New York Times’ list of the 30 greatest living American songwriters.