Before Matt Taibbi was sparring with Democratic members of Congress on Capitol Hill earlier this year over the Twitter Files, he was a darling of the progressive left, appearing regularly on shows like Democracy Now! and others hosted by Bill Moyers and Rachel Maddow. Though he was always a fierce critic of the Democratic establishment, the rise of Donald Trump suddenly meant that anyone nominally left of center—including progressive journalists like Taibbi—was expected to support Hillary Clinton unconditionally. So when he attacked her as a sellout, argued that the Russiagate narrative was mostly bullshit, and equated the manipulative tactics of right and left media personalities, progressives gave him the cold shoulder. Elected Democrats started treating him like a puppet of the right. In 2020, Taibbi started publishing his work on Substack and quickly became one of the platform’s most popular writers, earning far more than he ever did at Rolling Stone, where he had been chief political reporter. He became even more of a pariah by publishing exhaustive reports that documented how the government sought to control what was said on Twitter about COVID-19 and efforts by Russia to influence U.S. elections. Congressional Democrats unconvincingly pilloried him as a fake journalist, an apologist for Vladimir Putin, and a stooge for Elon Musk. I caught up with Taibbi at FreedomFest, an annual gathering held this year in Memphis, to talk about the new challenges to free speech, why legacy media is dying, and how identity politics are poisoning political discourse.