Skip Bayless has never quite been known to mince words. However, this time around his target was the former New England Patriots superstar and the NFL GOAT, Tom Brady.
The seven-time Super Bowl champion recently signed a 10-year, $375 million contract with Fox as a commentator. This was followed by Brady's purchase of a 5% stake in the Las Vegas Raiders, a transaction that was approved unanimously by 32 NFL owners.
“This is so wrong. It’s such a bad look for everybody involved starting with Tom Brady. I defended him for years. He is the runaway GOAT, was as a quarterback. And now in retirement the runaway GOAT is trying to flex and flaunt. He is bullying this league. He is big-footing this league,” Bayless explained during his appearance on The Arena: Gridiron show.
“Tom Brady is F you’ing the entire league and my former network… He should just drop the Fox deal."
Skip Bayless did NOT hold back on Tom Brady being in the coaches' box 🗣
(via @ArenaGridiron)pic.twitter.com/xyJCGNcmDg
— NFL on ClutchPoints (@ClutchPointsNFL) September 17, 2025
The controversy had worsened when Brady was recently seen sitting in the Raiders’ coaches' box during the loss against the Los Angeles Chargers on Monday Night Football.
“5% is worth $400 million. I fell out of my chair last night when I saw him sitting in the coaches box with a headset on… He is blatantly ‘f-you’ing’ the entire league and my former network,” Bayless said.
I have defended Tom Brady for years as the runaway NFL GOAT. But now he wants his cake and eat it, too? He took a reported $370 mil for 10 years from Fox then bought 5% of the Raiders, which severely limits his ability to do his Fox job? Now he's advising/coaching? Big-footing.
— Skip Bayless (@RealSkipBayless) September 16, 2025
Skip believes that purchasing the 5% stake is a major problem for Fox as players and coaches will not want to confide in him.
“The players and coaches are going to confide in you. They are going to open up to you. Now, if I’m the Bears, I am shutting up, man. I am closing down. He should just drop the Fox deal,” Bayless said.
Raiders head coach Pete Carroll recently stated that he talks to Brady regularly, with Bayless posting multiple follow-up tweets on X.
Wait, Raiders owner Tom Brady is sitting in the coaching box with a headset & ESPN says he talks often during the week to O.C. Chip Kelly??? How can the NFL allow Brady to even remotely interview players/coaches of other teams as part of his Fox prep? This is just wrong.
— Skip Bayless (@RealSkipBayless) September 16, 2025
Brady is yet to publicly comment on the matter, with the NFL recently stating that there were no rules that prohibited a part-owner from sitting in the coaches' booth or wearing a headset during a game.