Skip Bayless Slams Tom Brady Amid Growing Backlash for Dual Roles With Raiders, Fox

Week 2 of the 2025 NFL season delivered fireworks on the field, with more than 800 points scored across the league.

Yet as Monday night’s divisional clash between the Los Angeles Chargers and Las Vegas Raiders wrapped up, the conversation quickly shifted away from the scoreboard.

All eyes were on Tom Brady, whose appearance in the Raiders’ coaches’ box sparked a new wave of controversy.

What Is the Controversy Surrounding Tom Brady’s Role With the Raiders and Fox Sports?

Former Patriots legend Tom Brady, now a minority owner of the Raiders, was seen inside the coaches’ box with a headset on. While that alone raised questions, the issue runs deeper.

As Pete Carroll confirmed, Brady has been working closely with the Raiders’ offensive coordinator, Chip Kelly, while still fulfilling his role as a lead broadcaster for Fox Sports.

That unique dual role gives him access to rival teams for interviews, blurring the line between his ownership interests and media obligations.

Analysts and fans alike pointed to the glaring conflict of interest. For Fox, Brady is tasked with gaining insights from opposing players and coaches.

For the Raiders, however, he holds a stake in shaping the team’s football operations. As Skip Bayless argued, “it’s such a bad look” for the NFL and “everybody that is involved.”

Bayless went further, saying Brady has put the league in a no-win situation. “He’s bullying this league. He took a deal to work for Fox, 10-years for $375 million,” Bayless said on his show.

“Then, he turned right around on top of that, and he bought five percent of the now Las Vegas Raiders… He is blatantly ‘f-you’ing’ the entire league and my former network.”

The incident reflects a larger trend of overlapping interests within professional sports. As highlighted, the NFL itself now owns a stake in ESPN and, by extension, profits from gambling tied to ESPN Bet.

For critics, Brady’s highly visible presence in the Raiders’ booth is just the latest and most public example of blurred ethical lines.

Bayless argued that the most straightforward solution would be for Brady to step away from broadcasting altogether.

He warned that players could begin withholding information if they fear it may indirectly benefit the Raiders.

“His duties as a Fox broadcaster allow him… to obviously interview all of you the day before he would commentate on your game.”

Bayless argued that this overlap in responsibilities puts Brady in a position where the playing field is no longer level.

Still, with a reported nine-figure contract on the line, Brady seems unlikely to walk away from Fox. That leaves the NFL facing a potential credibility crisis.

Without firm guidelines to prevent conflicts of interest, both Brady and the league could see their reputations tested in the long run.