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Tom Brady Always Knew This Was Possible

For years, Brady has talked about possibly playing for a team other than the Patriots. Even if he was joking, he always knew it could happen. He knows how business is handled in New England.

I don’t remember exactly when the conversation happened, but it was at some point around when the Patriots played San Francisco in 2012, and after the deal for the 49ers’ new stadium was done. It was in the New England locker room, on a weekday, and I mentioned to Tom Brady a conversation I’d had with someone else about Candlestick Park, where his dad was once a season-ticket holder.

You realize you’ll retire never having played there?

By weird happenstance, he hadn’t before. The NFL’s 2002 realignment and scheduling formula changes made it so Brady didn’t play his hometown team until his sixth year, 2005. That one was at Gillette. The Patriots then visited Candlestick in 2008, the year Brady lost to a torn ACL. And by the time they go back, in 2016, Levi’s Stadium would be finished and Candlestick would be gone. It was something, in the moment, I don’t think he’d considered.

He fired back: Well, I’ll probably get traded to the Rams or something and play there.

Brady, clearly, was joking. But there was a layer of truth in how he responded. The kid from San Mateo, who grew up idolizing Joe Montana, was a teenager when his hero got traded to the Chiefs. He didn’t enter the league as a high draft pick, entitled to a headline spot in the organization that picked him. And he hadn’t even started his fourth year, when he was dealt a strong reminder that the NFL is a business—and that no one is exempt from that reality.

That September, one of his best friends on the team, and a captain on the Patriots’ first Super Bowl team, Lawyer Milloy, was unceremoniously dumped just days before the season opener, after Milloy refused to take a pay cut. People around Brady would always tell you that one stuck with him.

Brady and the Patriots won their second Super Bowl that fall, won again the year after, and would go on another run a decade later to their fourth, fifth and sixth Lombardi trophies. Along the way, the quarterback won an unprecedented four Super Bowl MVPs, along with three regular-season MVPs.

But my sense is that he was unlike most of the few athletes who have reached the level that he has. He never assumed he was entitled to finish his career where he started.

In fact, there were times, like the one I explained above, when it seemed like he assumed that, like Montana or his old buddy Milloy, that wouldn’t happen. And maybe that’s why it ended like it did on Tuesday morning, with simple posts on Instagram and Twitter.


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There will be a lot of blame assigned, of course, for why the greatest pairing in NFL history—the partnership between Brady and coach Bill Belichick—had to screech to a halt like this, but, in a way, it might’ve been inevitable, and the result of what both of these guys were able to accomplish over two decades.

On one side, you had the coach who’s unrelentingly disciplined in how he runs his organization, and how he separates professional relationships from personal ones. He won’t let players age on his roster with big financial numbers. He won’t coach the quarterback much different than he does a gunner on the punt team. And Brady, in his willingness to take less, and fight age, and take hard coaching, enabled all of it.

The message to the rest of the team: If he can pay and coach Tom Brady that way, I better sit up straight and not complain.

On the other side, you had the player who entered the league as a sixth-round pick, and grew into a brand of his own; who’d lived within the old-school, disciplinarian culture for longer than anyone; who’d been leveraged in contract negotiations, and used as an example for his younger teammates not just in how to do things, but also how much crap to take. It’s fair to think than anyone, even someone like Brady, would eventually get worn down by it.

But for 20 years, it worked to an unprecedented level. The Patriots won more Super Bowls than the Niners Brady cheered for as a kid did, and Brady himself took home more Super Bowl MVPs than his hero Montana. A team that was once the NFL equivalent of the L.A. Clippers became the seventh most valuable sports franchise on the planet, just behind Manchester United and just ahead of L.A.’s other basketball team, the Lakers.

The ending? Well, it probably wasn’t what anyone envisioned.

Yes, Robert Kraft and Brady met. But there was no great last-ditch effort by Belichick to hold onto the quarterback that he’ll be forever connected to. Instead, the coach, ahead of free agency, talked to Brady over the phone and told him where he stood.

In the end, it was just business—and probably just as Brady himself expected.

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