What Jason Whitlock’s Role at Outkick Really Means for His Career

Sports media is built on polarizing personalities. Skip Bayless, Colin Cowherd, and regional figures like Mike Francesa — all are generally considered abrasive even by their fans. It’s a hard line to walk; not every larger-than-life voice is capable of pulling it off. Jason Whitlock, for his entire career, has landed in this space.

His uncompromising style gets him repeated shots at high-profile media positions. But his latest endeavor could be the end of this part of his career. Let’s look at Whitlock’s time in sports media and his latest project.

Jason Whitlock’s fraught sports media career

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Whitlock’s sports bona fides stem from his time on the field. He played football for Division I school Ball State, according to The Daily. Injuries marked his final year of eligibility, so he dropped out of the game entirely. He put his sights straight to sportswriting in 1992, covering the team he just finished playing for.

By 2002, he worked his way up the newspaper ranks with his provocative writing enough to catch ESPN’s attention. He worked for several years as a regular guest on ESPN programs. The Big Lead notes that this stint was cut short in 2006 when Whitlock disparaged several coworkers in an interview.

His time with Fox, mostly writing Fox Sports on MSN columns and guesting on radio programs, ended roughly. Hyphen Magazine caught on to a horrid tweet that involved racism and sexually-charged content about then-New York Knick Jeremy Lin. It was too much for Fox; they cut him loose in 2012.

Whitlock’s biggest contracts and fastest flameouts

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On an episode of the B.S. Report Whitlock revealed he was in talks to return to ESPN. At this point, the looming Fox Sports One competing channel worried the network. The stock for attention-grabbing controversial sports personalities was high. So Whitlock was back on board, signing yet another major sports media contract.

This excursion was his shortest yet. ESPN had big plans for Whitlock and gave him the reins of a new website called The Undefeated. It was meant to be like Grantland from an African-American perspective. The site’s launch dragged on for months. Eventually, Deadspin revealed the cause: Whitlock’s unstable leadership. The network ousted him once more.

Fox Sports One, in the business of courting controversial figures, swiftly signed Whitlock, reports Inside Hook. They paired him with their reliably controversial Cowherd. After two years, Whitlock yet again moved on from a major media position. This time, it involved money. The network offered to re-up Whitlock’s contract but declined to offer a raise.

What Whitlock’s latest role means for his career

Whitlock’s next move appears to be a downward turn. Clay Travis, another FS1 personality, runs an independent sports outlet called Outkick. A Forbes interview with Travis illuminates the purpose of the effort: to court controversy.

It’s seemingly a great fit for the blog’s latest hire, Whitlock. In his first column, the cranky ex-Fox firebrand says so. “It’s hard to be me at a modern mainstream media company,” Whitlock wrote. “Racial polarization, the promotion of anecdote-driven worldviews and the silencing of ideas and thoughts that contradict mainstream media narratives are tearing America apart.”

He’ll likely flourish there, as long as he stays on Travis’s good side. Reading between the lines of this move, though, it’s hard to imagine that this ideological fit is exactly where Whitlock’s long-running career should be.

He now works for a blog run by one of his previous co-workers. That lack of media conglomerate muscle might be freeing for Whitlock’s baiting approach to sports coverage. But it is unlikely to come with a paycheck to match.