Charlie Sykes On The Mob-Boss Presidency

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Jan 16, 2026

Charlie Sykes, a seasoned journalist and former conservative talk-show host, explores the complexities of today's political landscape. He shares insights from his contrarian upbringing and how it shaped his views. Sykes discusses the dangers of audience capture and the tribalism in modern discourse. He reflects on the rise of talk radio, the influence of figures like Gingrich and Limbaugh, and how they transformed conservatism. Additionally, he critiques the failures of both parties and the changing dynamics of political argument.

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ANECDOTE

Contrarian Childhood Shaped Independence

Charlie Sykes grew up in a contrarian, debate-filled household that shaped his independence.
He credits childhood argument culture for making him comfortable walking away from groups and pursuing an independent career.

ANECDOTE

Early Political Education With Eugene McCarthy

Charlie's father ran Eugene McCarthy's 1968 Wisconsin campaign and gave him early political exposure.
Young Charlie flew to rallies and met McCarthy, which deeply influenced his idea of political leadership.

ANECDOTE

Conversion To Catholicism In College

Charlie converted to Catholicism in college after reading Lewis, Chesterton, and Newman.
He was baptized around age 19 or 20 and says the conversion was one of his life's most important moments.

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Charlie is a journalist and podcaster. From 1993 to 2016, he hosted a conservative talk show on WTMJ in Milwaukee. He was also the editor of Right Wisconsin, the editor-in-chief of The Bulwark, and a commentator on MSNBC. He recently went fully independent with his own substack, “To the Contrary” — subscribe! The author of many books, the latest was 2017’s How the Right Lost Its Mind.

An auto-transcript is available above (just click “Transcript” while logged into Substack). For two clips of our convo — on the Trump admin’s soulless response to the ICE killings, and if the GOP is starting to turn on Trump — head to our YouTube page.

Other topics: growing up in a contrarian liberal home; his dad a journalist prof who ran Eugene McCarthy’s 1968 campaign in Wisconsin; Charlie converting to Catholicism in college; TS Eliot’s influence on his faith; writing his first book based on his dad’s essay against academia; getting into talk radio in the early years; the Limbaugh effect; the MSM disdain over talk radio; my early campaign for marriage equality reaching Charlie’s show; the lost culture of healthy debate; Gingrich’s contempt for the opposition; Vince Foster; Bush discrediting conservatism; the demonization of Obama; the failure of GOP gatekeepers; both parties embracing mass migration; “The Flight 93 Election”; the groups controlling the Dems; Biden empowering Trump on immigration; the Fox News fallacy; the anti-Semite card with respect to Israel and the settlements; Gaza; the war in Ukraine; the ICE killing in Minneapolis; JD’s soulless presser; the indecency of Matt Walsh and Megyn Kelly; the threats to Greenland; the persecution of Jerome Powell; civil war rhetoric; the Caribbean boats and Maduro’s ouster; our Viking foreign policy; Cardinal Dolan embracing MAGA; Pope Leo replacing Dolan; tariffs as protection money; the abuse of the pardon; ICE recruitment ramping up; and how dogs are the best people.

Browse the Dishcast archive for an episode you might enjoy. Coming up: Kevin Williamson on the devolution of the GOP, Jeffery Toobin on the pardon power, Jason Willick on trade and conservatism, Vivek Ramaswamy on the right’s future, and Michael Pollan on consciousness. Please send any guest recs, dissents, and other comments to dish@andrewsullivan.com.