# Charlie Sykes

> Charlie Sykes spent 23 years as one of Wisconsin's most influential conservative talk-radio voices, then walked away and turned his fire on his own movement. He co-founded The Bulwark, became a fixture of the Never Trump opposition, and now writes the Substack newsletter and hosts the podcast 'To the Contrary.' Author of nine books and an MSNBC contributor, he is a rare media figure who publicly reckoned with the part talk radio played in remaking the American right.

- **Role:** Author of 'To the Contrary' newsletter and host of 'To the Contrary with Charlie Sykes' podcast; MSNBC contributor
- **Organizations:** To the Contrary (Substack), The Bulwark, The Weekly Standard, MSNBC, WTMJ, Milwaukee Magazine
- **From:** Seattle, Washington, USA
- **Nationality:** American
- **Education:** High school, Nicolet High School, B.A. in English, summa cum laude, University of Wisconsin-Milwaukee
- **Known for:** Hosted a dominant Wisconsin conservative talk-radio show for 23 years (1993-2016), Author of nine books on higher education, culture, and politics, Co-founder of The Bulwark, a leading center-right anti-Trump media outlet

## Career timeline

- **1975** — Staff writer at The Northeast Post, a weekly in West Allis, Wisconsin
- **1976** — Joins The Milwaukee Journal; later covers the Milwaukee City Hall beat
- **1982** — Moves to Cleveland as a staff writer for Cleveland Magazine
- **1983** — Returns to Milwaukee as managing editor of Milwaukee Magazine
- **1984** — Becomes editor-in-chief of Milwaukee Magazine
- **1988** — Publishes first book, Profscam
- **1989** — Begins talk radio as a substitute host at WISN in Milwaukee
- **1993** — Starts his long-running morning talk show on WTMJ and hosts Sunday Insight on WTMJ-TV
- **2016** — Ends 23-year WTMJ radio run; emerges as a prominent Never Trump voice
- **2017** — Publishes How the Right Lost Its Mind
- **2018** — Co-founds The Bulwark; launches The Bulwark Podcast
- **2024** — Leaves The Bulwark on February 9, citing a desire for a slower pace
- **2025** — Launches the Substack newsletter and podcast To the Contrary

## Achievements

- Hosted a dominant Wisconsin conservative talk-radio show for 23 years (1993-2016)
- Author of nine books on higher education, culture, and politics
- Co-founder of The Bulwark, a leading center-right anti-Trump media outlet
- Former editor-in-chief of The Weekly Standard
- Longtime national television commentator and MSNBC contributor
- Influential figure in the Never Trump movement

## Latest updates

- **2024-02** — Departed The Bulwark after roughly five years of daily podcasts and newsletters, opting for a more measured pace while continuing MSNBC commentary.
- **2025-02** — Launched the Substack newsletter and weekly podcast 'To the Contrary with Charlie Sykes.'

## Links

- Website: https://charliesykes.substack.com/
- Twitter/X: https://x.com/SykesCharlie
- YouTube: https://www.youtube.com/@charlessykes9046
- Bluesky: https://bsky.app/profile/sykescharlie.bsky.social

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Profile page: https://yespress.io/charlie-sykes
Published by YesPress — https://yespress.io
Last updated: 2026-06-02