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Tom Brady Retires as a Monument to Obsession

Esquire 3/10/2023 Jack Holmes

"Good morning guys, I'll get to the point right away," Tom Brady said, looking into his phone camera from what appeared to be the top of a Floridian dune. "I 'm retiring. For good. I know the process was a pretty big deal last time," he said, glancing down with a touch of self-awareness. "So when I woke up this morning, I figured I'd just press record and let you guys know first." And then, a few seconds later, the words caught at the top of his throat. "Thank you guys so much to every single one of you for supporting me. My family, my friends, my teammates, my competitors," Brady said, "Thank you guys for allowing me to live my absolute dream. I wouldn't change a thing."

For perhaps the first time when it comes to the life of Tom Brady, you wondered whether that was really true. Sometimes I think about how I'll never make a billion dollars because I'd be satisfied with way less than a billion dollars. The people who do make that kind of money, with surely some exceptions, are never satisfied with any amount of money. Obsession is a funny thing. It is an engine for success, a rocket ship that carries those caught within it to the most dizzying heights, and yet often it can send them crashing back to earth moments after they arrive amongst the stars. Most professional athletes have it. The greatest always have it. Those untold hours in the gym and on the practice field, untold more studying tape, the superhuman discipline in diet and lifestyle. There are some people whose unbelievable natural ability allows them to skirt a few corners. For every Tim Duncan, there's a Shaq. For every Cristiano Ronaldo, there is a Ronaldinho. But Ronaldinho's name never appears next to "GOAT."

Tom Brady's does. A New Yorker I may be, and we love our gags about Eli Manning and his Kryptonite, but the Boston-haters gave up denying reality long ago. The man has won the Super Bowl seven times. He's appeared in 10. He was MVP in five of them. He was regular season MVP three times. He's the all-time leader in passing yards and completions and touchdown passes and wins by a starting quarterback. He won his first ring in February 2002, at the age of 24. He won his last in February 2021, at 43. That last championship was the only one he secured without Bill Belichick and the famed New England organization around him. It was, in a way, the ultimate testament to his greatness: he could win anywhere, at any age. He never did it on his own, to be sure, but the key ingredient was always Tom Brady. The win with the Tampa Bay Buccaneers was, potentially, the perfect bookend to a near-incomprehensible career—the end of all discussion about his place in the game.

How long did Brady linger to take in the view each time he reached the mountaintop? © Getty Images How long did Brady linger to take in the view each time he reached the mountaintop?

But it wasn't enough. Nothing ever was. It would be fascinating to have some look into the minds of the dozens of players on a Super Bowl champion team, some way to observe how long each of them relished the moment, basked in the afterglow, allowed themselves to stop the locomotive in their minds that had driven them forward, day after day and game after game, from high school ball through college, through the middling seasons with mediocre teams they powered through at the professional level to reach this, the summit, what they saw in their mind's eye while staring at the ceiling in their childhood bedrooms. Some guys, you've got to think, do some laurel-resting through much of the following summer. With others, you wonder if the feeling of satisfaction even lasted weeks, days. The drive that had brought them to this point may be truly unstoppable. Even holding the Super Bowl trophy, their eyes flit towards the next one, the next season, the next game, the next practice, the next tape session. They did not summit a mountain after all. It was a lap on a track.

And then you're forced to wonder if that is what separates them from the merely very good, the greatest from the great. A few degrees of obsession that cause things to boil over, that risk losing any sense of equilibrium. Tom Brady passed on the chance to make his last Super Bowl victory a bookend, then he passed on his own decision to retire a year later. At the time, last summer, the tabloid media was awash in stories that his marriage was beginning to wilt next to this inextinguishable fire. He had decided to return for another season of punishing NFL football in his mid-40s, to expose himself to hits from 6 '6", 240-pound people who run 40 yards in four seconds. Whether or not this decision was the cause, Brady announced he and Giselle Bundchen had finalized their divorce in October, a couple of months into the season.

It was not a season to remember—even if Brady, in all his inevitability, got himself into the playoffs. They were swiftly sent packing in the Wild Card Round by the Dallas Cowboys, and now Brady has announced he's on his way more permanently. But will this, even this, really be the end? It's not impossible to see a swan-song season back in New England, or a jaunt up to San Francisco to become the latest quarterback to slot into an all-around formidable squad. Those paths offer the allure, the tantalizing possibility, of a final chapter befitting the book. Those are rare in athletic careers, though, and not just because of all the externalities that have to align for even the greatest players to have a great season.

That's the enduring allure of sports: its capacity to continually produce the unexpected. Pure unpredictability. And it's the same chaos that the great ones attempt to tame through their own force of will. They are insatiable, willing to sacrifice everything. In the end, we can only hope they were able to linger at the summit and take in the view. That looking back now, they still think it all was worth it.

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