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When will Tom Brady join Fox?

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From the Super Bowl LI 28-3 comeback to the "Tuck Rule Game," Mike Florio and Chris Simms look back at some of the most iconic moments from Tom Brady's illustrious career.

Now that Tom Brady has retired from football, he’ll eventually embark on his next career of talking about football.

Last year, Brady struck a 10-year, $375 million contract with Fox to become the network’s No. 1 analyst. Given that he’s done with football, he can start working for Fox.

Andrew Marchand of the New York Post reports that Fox executives are unlikely to put Brady in the booth for Super Bowl LVII in 11 days. That seems like the obvious play. Current No. 1 analyst Greg Olsen has seen his star rise during the current postseason, an ascension that has coincided with the perception that Tony Romo, the No. 1 analyst at CBS, has faded. It would make no sense to supplant Olsen for Brady for the biggest game of the year.

As Marchand notes, it’s possible that Brady will be part of the Fox pregame coverage. That makes sense, primarily since pregame coverage typically fills five or six hours.

Still, at some point, Olsen will be out and Brady will be in. Unless Fox decides to go with a three-man booth. Which, frankly, most high-end broadcasting talent refuse to even entertain.

So if/when (when) Brady’s arrival knocks Olsen down to the No. 2 team, Olsen will become the sympathetic figure -- and Brady will be relentlessly scrutinized by anyone and everyone who hopes to draw a contrast between Brady and his predecessor.

It will put plenty of pressure on Brady. And, yes, he has thrived under pressure for years. But this is an entirely different kind of pressure, and an entirely different kind of performance.

Unless he chooses not to do it (which would entail giving up a lot of money), Brady will be in the booth at some point. It’s been suggested that maybe he’ll take a year off. But that would only give Olsen another year to become even more entrenched before he inevitably gets the tap.

So we’ll see what happen. And while it’s hard to feel sorry for a guy who’ll make $37.5 million per year, Brady’s next act won’t be as easy to navigate as it may seem.