It’s weird what sticks with you. For me, it was a television segment during the summer of 2008. I’d just moved back to Massachusetts from Texas, and on the screen behind me was a picture of Tom Brady at the end of Super Bowl XLII, with a tagline that played off the title of a Buster Olney book on the Yankees reading, “The Last Night of the Patriot Dynasty?”

Brady was turning 31. The core around him—the group he grew up with and had won three Super Bowls and got to 18–0 with in 2007—had aged significantly. Bill Belichick was 55, and New England had started to bleed lieutenants, with scouts and coaches leaving for new opportunities elsewhere. So we were trying to see the future for the team, and the quarterback, and put in perspective the historic run we’d just witnessed.

What a joke that turned out to be.

That was nearly 15 years ago.

Belichick and Brady made nine Super Bowl appearances for the Patriots, winning six world titles.

Kirby Lee/USA TODAY Sports

Brady’s retired, again, and we all have stories of where we were when he was coming up. I was a freshman and sophomore at Ohio State the two years he started at Michigan and can remember being in the front room of my frat house for the “Tuck Rule” game my senior year. People graduating high school this spring weren’t alive for his first three championships.

And so, for me, the obvious first takeaway from Brady finally calling it quits is the obvious one—the guy didn’t just define his generation of football players; he actually connected generations. The Buccaneers’ top draft pick this year, Logan Hall, who is 22, was born a week after Brady was drafted by the Patriots. The punter Brady played his first two years, Lee Johnson, is now 61. The Patriots’ left tackle his rookie year, Bruce Armstrong, is 57.

So Sunday, sitting in the Lincoln Financial Field press box, I thought about all this in a slightly different context, with the 49ers’ quarterback situation unraveling. My immediate thought, of course, as the game slipped from San Francisco’s grasp, was whether Brady would consider rescuing his hometown team—arriving in 2023 for a 24th season to stabilize the most important position on a loaded roster.

Then, I considered how ridiculous it was that the idea was actually a really normal thought. The 49ers couldn’t keep their quarterbacks healthy, and were effectively on their fifth guy at that point, having gone from Trey Lance to Jimmy Garoppolo (once drafted to back up Brady in his 15th season) to Brock Purdy to Josh Johnson and then, finally, to a bootleg version of Purdy, who literally couldn’t throw because the Niners literally ran out of QBs.

A few weeks after that liveshot in 2008 asking whether it was the end of the Patriot dynasty, Brady tore his ACL and MCL against the Chiefs. The injury cost him the final 15 games of the season, and led to a painful and sideways rehab process. He made it back for Week 1 that year, for the 14 seasons to follow, and for his final game three Mondays ago, without missing a single start due to injury.

Which made it, again, normal that I, or anyone else, would be thinking that the Niners’ elixir for a quarterback durability problem on the roster would be acquiring a guy who will turn 46 in August for his 24th year of professional football, a sport in which the injury rate is 100%.

But that’s who Brady was, and over time, we’d learn.

In 2008, we all thought the normal rules applied to him. Terry Bradshaw was 31 when he won his final Super Bowl. Joe Montana was 33. So the idea that Brady might have trouble winning one again, or that the Patriots (or the Buccaneers) wouldn’t be able to scale that mountain another time, was pretty rational.

And, now, that idea looks stupid.

So much as he tried to tell us and show us that the rules that apply to the rest of us, and even the rest of pro football, never applied to him.

A few more takeaways from Brady’s second retirement …

• His decision absolutely impacts the 2023 quarterback market. For many of the reasons Brady would’ve made sense for those Niners, San Francisco will have to consider its readiness to rely on two young quarterbacks—Purdy and Lance—coming off injury. The Raiders would’ve been in on Brady, and now they’ll have to look elsewhere, maybe to Garoppolo. And having those two potentially in on other quarterbacks would have a trickle-down effect on how things play out over the next two months.

• The next domino to fall should be Derek Carr. The Raiders are working on trade possibilities, and have until Feb. 15 to agree to a deal before his $32.9 million base for this year, and $7.5 million of his money for 2024, vests as fully guaranteed. I still think the most likely scenario is he gets released that week and gets a one-month jump on free agency. But one of the NFC South teams, or maybe the Jets or Commanders, could make a move earlier.

• The Buccaneers will have to decide whether or not now is the time to rip the Band-Aid off with all the money they pushed into future years to create their three-year championship window with Brady as their quarterback—they currently are $55 million over the 2023 salary cap, according to These things can always be massaged, of course, but if the Bucs can’t land a high-end veteran quarterback, it’s definitely worth asking if now is the time to turn the page on some older players, and reset themselves to get to ’24 with the books clean.

• For the record, what the Buccaneers did the past three years was 100% worth it. They won a championship, and contended for two (plus, won their division in the third year). So if they have a painful year in 2023 as a result, well, that cost of doing business is pretty small in comparison to what they got out of three seasons with Brady.

• And on the flip side of that arrangement, the past three years definitely further burnished Brady’s legacy. He won one Super Bowl without Belichick, who I still believe is the greatest coach of all time, and the Patriots clearly weren’t the same absent No. 12. Consider this—Brady’s worst record in 18 seasons as New England’s starter was 9–7, and that 9–7 came in 2002. The Patriots went 7–9, 10–7 and 8–9 in their first three years without him. Which means, while both guys are historically great sports figures, we can declare a winner in the Brady-Belichick argument.