The Big Lead

Tom Brady’s coaching booth cameo sparks fiery reaction from Skip Bayless

Skip Bayless blasts Tom Brady after the Raiders legend was spotted in the coaching booth during Monday Night Football, raising questions about his dual role in the NFL.

By Yagya Bhargava

Tom Brady walks the red carpet on Sunday, May 25, 2025, ahead of the 109th running of the Indianapolis 500 at Indianapolis Motor Speedway.
Tom Brady walks the red carpet on Sunday, May 25, 2025, ahead of the 109th running of the Indianapolis 500 at Indianapolis Motor Speedway. / Michelle Pemberton/IndyStar / USA TODAY NETWORK via Imagn Images
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Week 2 of the 2025 National Football League season brought plenty of fireworks with over 800 points scored across all games. But the real controversy started after Monday night's Chargers-Raiders divisional showdown wrapped up.

Cameras caught Tom Brady in the Las Vegas Raiders' coaches' box wearing a headset, and that image sparked immediate debate. The Patriots legend, who now owns a minority stake in the Raiders, has reportedly been working closely with offensive coordinator Chip Kelly, according to Pete Carroll.

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Brady also serves as Fox Sports' lead NFL broadcaster, which means he gets access to rival teams for interviews and preparation. It's a situation that creates obvious conflicts between his media role and ownership responsibilities.

Skip Bayless didn't mince words about Brady's dual roles, calling it "playing both sides" and labeling it "a bad look" for everyone involved.

"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 Brady situation highlights a growing problem across professional sports where business interests overlap in ways that blur competitive lines. Many view Brady's prominent ownership role as the most visible example of these blurred boundaries becoming problematic.

Tom Brady
Former NFL player Tom Brady on the field before the game between the Dallas Cowboys and the Las Vegas Raiders at AT&T Stadium. / Tim Heitman-Imagn Images

Bayless suggested the simplest solution would be Brady stepping away from broadcasting entirely. He warned that players might hold back information during interviews if they suspect it could benefit the Raiders.

With Brady's massive nine-figure Fox contract on the table, stepping aside seems highly unlikely. That leaves the league facing a potential credibility issue that could damage both Brady's reputation and the NFL's image without clearer conflict-of-interest guidelines.

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