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Politics

The Democratic Party’s Crooked Kingmakers

Avery Collins
Last updated: October 6, 2026 7:53 am
Avery Collins
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On September 18, Jon Lovett, the former Barack Obama speechwriter and host of the political comedy podcast Lovett or Leave It, welcomed left-wing personality Hasan Piker to his show, calling Piker “the star of this year’s midterm elections” and “America’s sweetheart.”

Then, in a mock-serious tone, Lovett, a co-founder of Crooked Media, which produces the podcast, declared: “I do want to get this out of the way: I denounce you.”

That elicited a chuckle from Piker, who replied: “I denounce myself as well.”

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The hard-to-miss point was: All the controversy around Piker—the streamer has declared that “America deserved 9/11,” that accusations of Hamas committing sexual violence on October 7, 2023, are “rape fantasies,” that he would pick Hamas over Israel “every single time,” that the collapse of the Soviet Union “was one of the greatest catastrophes of the 20th century,” that “pound for pound” the U.S. is worse than Al Qaeda—was overblown.

Meaning it’s permissible—desirable—for Democrats to make room for Piker in their “big tent.”

“My view is: I am part of a pro-democracy coalition in the fight against fascism,” Lovett said, addressing Piker, “and it includes everyone from former Republicans like Nicolle Wallace and Tim Miller and Sarah Longwell, it includes establishment politicians, it includes Neera Tanden, it includes Shannon Watts, it includes AOC and Bernie, and it includes voices on the left like you.”

When I asked Watts, an anti-gun violence activist, how she feels about being lumped together with a streamer best known for his misogyny and antisemitism, she said: “What concerns me is the suggestion that, because the stakes are so high, we must overlook rhetoric or behavior we would otherwise reject.”

The deeper problem, Ravi Gupta, a Democratic podcaster, told me, is that Lovett and the rest of the Crooked team portrays themselves as a bunch of friends still in their post-adolescence just sitting around talking about politics, when, in fact, they are making huge decisions with long-term implications for the Democratic Party—like who belongs in the “pro-democracy coalition,” which candidates they’re leaning toward, which candidates they’re leaning against, what’s in, what’s out.

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