It’s weird what sticks with you. For me it was a TV feature in the summer of 2008. I had just returned 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 slogan playing from the title of a book by Buster Olney about the Yankees reading “The Last Night of the Patriot Dynasty?”
Brady turned 31. The core around him — the group he grew up with, with which he’d won three Super Bowls and gone 18-0 in 2007 — had aged significantly. Bill Belichick was 55, and New England had begun to bleed lieutenants while scouts and coaches sought new opportunities elsewhere. So we tried to see the future for the team and the quarterback and to put into perspective the historic run we had just experienced.
What a joke that turned out.
That was almost 15 years ago.

Belichick and Brady made nine Super Bowl appearances for the Patriots and won six world titles.
Kirby Lee/USA TODAY Sports
Brady is retired again, and we all have stories about where we were when he showed up. I was a freshman and sophomore at Ohio State for the two years that he started in Michigan and can remember being in the living room of my sorority house playing the game Tuck Rule during 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 that Brady finally quit is the obvious one — the guy didn’t just define his generation of soccer players; he actually connected generations. Logan Hall, the 22-year-old Buccaneers’ top draft pick this year, was born a week after Brady was drafted by the Patriots. Punter Brady played his first two years, Lee Johnson, is now 61. The Patriots’ left tackle against his rookie year, Bruce Armstrong, is 57.
Sitting in the press box at Lincoln Financial Field on Sunday, I thought about all of this in a slightly different context as the 49ers’ quarterback situation unraveled. Of course, when the game slipped away from San Francisco, I immediately thought about whether Brady would consider rescuing his team from his hometown — he arrived in 2023 for a 24th season to stabilize the key position in an overloaded roster.
Then I thought how ridiculous it was that the idea was actually a perfectly normal thought. Unable to keep their quarterbacks healthy, the 49ers were effectively on their fifth man at this point, having moved from Trey Lance to Jimmy Garoppolo (once drafted to support Brady in his 15th season) to Brock Purdy to Josh Johnson and then, eventually to a bootleg version of Purdy who literally couldn’t pitch because the Niners were literally running out of QBs.
A few weeks after that liveshot in 2008, while asking if this was the end of the Patriot dynasty, Brady ripped 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 into Week 1 this year, into the 14 subsequent seasons and into his final game three Mondays ago, without missing a single start through injury.
What it did again normal that I or anyone else would think that the Niners’ elixir for a quarterback stability issue on the roster would acquire a man who turns 46 in August for his 24th year of professional football, a sport where injury rates are high is 100%.
But that was Brady, and in time we would learn.
In 2008 we all thought normal rules applied to him. Terry Bradshaw was 31 when he won his last Super Bowl. Joe Montana was 33. So the idea that Brady might have trouble winning another one or that the Patriots (or the Buccaneers) might not be able to climb that mountain another time was pretty rational.
And now that idea looks stupid.
As 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 professional 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 have made sense for these Niners, San Francisco must consider its willingness to rely on two young quarterbacks — Purdy and Lance — who have recovered from injury. The Raiders would have found out about Brady and now they have to look elsewhere, maybe at Garoppolo. And potentially having those two with other quarterbacks would have a trickle-down effect on how things play out over the next two months.
• The next falling domino should be Derek Carr. The Raiders are working on trade opportunities 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 2024 cash are fully guaranteed. I still think the most likely scenario is that he will be released this week and given a month-long free-hand jump. But one of the NFC South teams, or maybe the Jets or Commanders, could make a move sooner.
• The Buccaneers must decide whether or not now is the time to rip the patch with all the money they’ve poured into the coming years to complete their three-year championship window with Brady at quarterback — they currently have 55 Millions of dollars too much according to overthecap.com’s 2023 salary cap. Of course, those things can always be massaged, but if the Bucs can’t land a high-end veteran quarterback, it’s definitely worth asking if they can now time to turn the page on some older players and reset to ’24 with clean books.
• For the record, what the Buccaneers have accomplished over the past three years has been 100% worth it. They won one championship and contested for two (plus won their division in year three). So if they’re having a painful year in 2023, that cost of doing business is pretty small compared to what they got out of three seasons with Brady.
• And on the flip side, the last three years have definitely continued to polish Brady’s legacy. He won a Super Bowl without Belichick, who I still consider the greatest coach of all time, and the Patriots clearly weren’t the same absent No. 12s. Consider this — Brady’s worst record in 18 seasons, when New England’s starter was 9 – 7, and the 9-7 came in 2002. The Patriots went 7-9, 10-7 and 8-9 in their first three years without him. That said, while both guys are historically great athletes, we can declare a winner in the Brady-Belichick argument.