For starters, Brady put into his contract last summer that it voids at the start of the 2020 league year (March 18) and that he cannot be hit with the franchise or transition tag. The quarterback cannot sign with any other team before March 18 and furthermore, he and his representatives cannot even speak to other teams until March 16, the day the legal tampering window begins.
With that being said, the Patriots can sign him to a new contract at any point — they have the exclusive rights to negotiate with him up until March 16.
What happens also has implications on the Patriots’ 2020 salary cap.
If Brady were to retire, the Patriots would have $13.5 million of dead money in 2020. If he re-signs with the Patriots prior to March 18, the number would be split over 2020 and 2021, so $6.75 million would be added to the Patriots’ 2020 salary cap. If Brady were to sign a new contract before March 18 and his 2020 cap hit was $20 million, it really would be $26.75 million.
If he were to sign with the Patriots or another team after March 18, there would be $13.5 in dead money for the Patriots in 2020. That means if Brady signs a deal with a $20 million cap hit with the Patriots after March 18, his cap hit would really be $33.5 million.
So, if the Patriots are going to bring him back, it makes a ton of sense for it to happen before March 18. But, that might be difficult to do because Brady wouldn’t get a true sense of what his value is on the open market.