Tom Brady balances regret over leaving too early with regret over staying too late

The latest testament to the uncanny longevity of Tom Brady‘s playing career comes from the fact that, 16 years after securing the top annual award from Sports Illustrated, he’s once again the Sportsperson of the Year. In a companion cover story with the magazine, Brady’s comments to Jon Wertheim illustrate a delicate balance that Brady hopes to achieve as he selects the perfect time to retire.

As his accomplishments grow larger and larger, the needle he’ll be trying to thread will become smaller and smaller. Put simply, he needs to avoid leaving too early, and staying too late.

“​​I imagine not playing,” Brady told Wertheim. “And I imagine watching football on Sundays going, ‘These guys suck. I could do way better than that.’ And then still knowing in my heart that I actually could still do it. If I stopped, I think I’d have to find something else that I’m pretty good at. And I don’t think that, you know, I’m going to be able to jump into something that has the same amount of excitement.”

That’s the on one hand position. Here’s the other.

“Regressing would be a very difficult thing for me to see,” Brady said. “As soon as I see myself regress, I’ll be like, ‘I’m out.’ I don’t really want to see myself get bad. So it’s just a constant pursuit of trying not to be bad.”

Father Time remains undefeated, even if Brady has staved him off longer than any NFL player has or perhaps will. If he’ll exit “as soon as” he sees himself regress, it opens up the possibility of an unexpected and sudden retirement, perhaps during training camp or even during the season. Would he finish a season that he has started even if he realizes that it’s ending if not over before the season ends? Surely, he’ll want to avoid being in that kind of situation, where he has no choice but to walk away from a team that had expected to have him for the full season.

That makes his effort in each offseason to evaluate the question of whether he can hold it together for another year critically important. He has made it clear that he’ll finish his current contract in Tampa, which runs through 2022. Then, it will become more challenging for Brady to know when to say enough.

There’s another element that Brady needs to be paying attention to, and it’s the dynamic that ultimately drove Hall of Fame coach Bill Parcells out of football. Once the losses create far more torment than the wins generate pleasure, it makes no sense to continue.

“I think if anything, the most challenging part is the emotional aspect of football for me,” Brady told Wertheim. “When we lose, it’s depressing. When we win, it’s a relief. It’s not like the joy, the happiness — it’s a relief. Because when we win, sometimes just winning isn’t good enough for you, because you expect perfection, and when you expect perfection and it’s less than perfect, you feel like there’s a down part to that.”

Maybe he’s always been that way. But if the only true enjoyment for Brady comes from the fleeting rush of adrenaline that occurs when hoisting the Lombardi Trophy (which to be fair lasts long enough for him to get Weekend at Bernie’s drunk on avocado tequila), the question of whether it’s worth all the effort and sacrifice and focus and stress will become louder and louder, the older and older he gets.