Why Skip Bayless Believes Tom Brady Now Might Reconsider Retirement

Perhaps it’s just wishful thinking, but Skip Bayless isn’t totally convinced Tom Brady is done.

Bayless last week said he heard the Tampa Bay Buccaneers would be pleasantly surprised if Brady returned for the 2022 NFL season, a notion that seemed to be validated Saturday when ESPN’s Adam Schefter and Jeff Darlington reported the quarterback was planning to retire.

Yet, after news of Brady’s impending retirement broke, his agent, his father and the Bucs all downplayed the report, casting some uncertainty over the seven-time Super Bowl champion’s actual plans. And Bayless now believes Brady could change his mind over whether to walk away this offseason.

“I’m here to tell you, knowing Brady the way I know him, that I heard (Sunday night) from several sources, from that inner circle, who said he and they are outraged over this — just the way you said they should be outraged,” Bayless said on Monday’s episode of “Undisputed” on FS1. “Because they wanted to make the announcement when they wanted to make the announcement, because he’s earned the right, I think, after all these years and all those Super Bowls and all those wins. He has earned the right to say, ‘Yes, this is it for me.’

“He went out of the country. They wanted to take some time to let it sink in. So, knowing him the way I know him, he is so competitive, he is so against the grain, that if you call his hand on him the way that ESPN did and say, ‘This is it, you’re retired’ — even though the phrase was ‘planning to retire’ — that it’s possible the door just got cracked about that far open. To where Tom Brady would come back from his trip, let the dust settle in his head and say, ‘Huh, I’ll show them.’ Because he’s been showing people since he was a sixth-round draft pick.”

Despite the confusion, all signs still point toward Brady retiring. Multiple NFL insiders, including Schefter, have continued to indicate such in the days since the initial report.

The holdup (and apparent frustration) instead seems to stem from Brady’s plans being leaked ahead of time. And while Bayless isn’t doubting the validity of ESPN’s reporting, he has seen enough from Brady over the years to know the QB often is motivated by feeling like he’s been wronged.

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Will that lead to a change of heart regarding retirement?

“As devastated as I was on Saturday, as chips started to fall the rest of the day and people dug in — such as (Don) Yee, (Bruce) Arians, (Brady’s) father — I started to get a little hopeful,” Bayless said. “It’s long-shot hope, probably, because you’re probably leaning the right direction that he left the country right after the loss thinking, ‘Yeah, I probably should call it a day now.’ But he might return to all this fallout and say, ‘You know what? I’m just gonna show them again. We’ll see what happens. Watch this.’ “

Farfetched? Probably. But an intriguing hypothetical, nonetheless.