Tom Brady's decision to retire puts Fox in the enviable yet still difficult discussion of what to do with Greg Olsen. Assuming Brady stays retired, of course. Olsen has been a fan favorite in his first year alongside Kevin Burkhardt as Fox Sports' new No. 1 booth in the post-Buck and Aikman era. He has garnered great praise during this postseason in particular for his ability to succinctly break down the how and why of crucial plays. He's young, had a great rookie campaign, and clearly has a lot of potential. In any other universe Fox would be in the perfect position right now.
Unfortunately, this universe is the one where the network paid Brady an ungodly amount of money last year to do Olsen's job whenever the QB decided to hang up the cleats. So much money that Brady has to be part of that No. 1 booth. But replacing Olsen with Brady would not only be disappointing for the viewers who grew to enjoy Olsen's commentary this year. It is also a huge risk. Olsen is now a known commodity, an analyst who will be good on most days and great on a few. Nobody knows how Brady will do in the booth with the red light on. Probably not even the man himself.
The worst-case scenario for Fox is shifting Olsen out of the top spot and replacing him with Brady, only for Brady to be bad. That would lock them into a full season of subpar broadcasts and make them a target for an avalanche of criticism for paying Brady so much money without actually knowing whether he'd be any good. Olsen's presence in the No. 2 booth and his work this year would serve as a strong contrast to what the broadcast could have been. It wouldn't be the end of the world but it would certainly be a dominating talking point for the entire season and nobody at the network nor the NFL would love that.