Charlie Sykes

Founder and Editor-at-Large, The Bulwark

Fast Facts

Charlie Sykes

Badger State Trump antagonist

Industry: Media
Key previous position: WTMJ Milwaukee
Education: U of Wisconsin, Milwaukee
Notable fact: Former Democrat

NJ50 Profile

“I can’t ever see going back to being a team member again,” said Charlie Sykes. Indeed, the former stalwart of conservative talk radio turned in his proverbial membership card to the GOP club back in 2016, when he publicly—and forcefully—distanced himself from the ascendant Trump movement.

After 23 years hosting one of Wisconsin’s top-rated shows, he laments that there may be no going back to radio, either. Most listeners, he says, are looking for a “safe space” free of dissenting voices. “Every host has either left the air or has become pro-Trump. At the moment, there is no business model that supports anti-Trump conservatives on the radio.”

A Trump-skeptical podcast and website, however? That does seem to be viable.

In 2018, Sykes founded The Bulwark, teaming with a group of exiles from the recently defunct Weekly Standard magazine, to produce smart conservative writing that manages to raise its eyebrow toward both political parties. Sykes, meanwhile, still flexes his radio muscles as host of the daily Bulwark Podcast, which has him interviewing other Republican apostates such as Trump primary challenger Bill Weld, campaign consultant Rick Wilson, and former Republican National Committee Chairman Michael Steele.

Initially, says Sykes, The Bulwark was intended simply as a “stopgap” while he and his colleagues figured out their next moves. “But we’ve been surprised by how much of a mark we’ve been able to make.” He says they’re looking to expand their output of podcasts and newsletters in coming months.

For Sykes, the real test for center-right Trump skepticism will come in 2020, especially if the Democratic Party nominates a progressive candidate like Bernie Sanders or Elizabeth Warren. On the one hand, conservatives will be able to “get back to doing what they do best, which is oppose the Left,” he said. “But at the same time, you don’t go back to a pre-Trump political world.”

It’s a realization he’s finally coming to terms with, as he makes peace with his political homelessness. “There’s still something surreal about being a complete political orphan,” he said, before joking: “One advantage I bring is that I’m an only child, so I’m kind of used to being on my own.”
Jeff Dufour