If the Buccaneers want to move on from Winston in 2019, then they should start by benching him for the duration of the season. If they play Winston in the coming weeks and he gets hurt, they will be obliged to pay his fifth-year option if he’s not healthy by the start of the next league year in March. Then they’d be on the hook for his $20.9 million salary for 2019, which would limit their ability to bring in another quarterback.
A similar situation transpired last season when Blake Bortles got wrist surgery after the 2017 postseason. His decision to play the rest of the season helped the Jacksonville Jaguars get into the AFC title game. But it also helped Bortles force the Jaguars’ hand in paying him. Because he might not have been healthy before the deadline, the Jaguars could have had to pay him for the year on his fifth-year option. Instead, Jacksonville extended Bortles on a new deal. (Whoops.)
In the case of benching Winston, the largest driving factor is likely that Ryan Fitzpatrick has been the better quarterback. The problem is that Fitzpatrick hasn’t been much better nor has he been consistently better. Thus, the Bucs have flipped back and forth between Fitzpatrick and Winston.
Logically, they could give Winston one more spin to see whether their young quarterback is worth an extension, especially if their season ends early through playoff elimination in a very competitive NFC South. At that point, which is coming very soon for Tampa Bay, they have nothing to play for but development and self-scouting for the offseason. Playing Winston would be a mistake, however. The Buccaneers should move on from him in the immediate future, and shouldn’t risk being financially tied to him for another year.
Winston should get interest in free agency, though his value couldn’t be lower. There are enough teams that could be in need of a veteran (Buffalo Bills, Jacksonville Jaguars, New York Giants, Baltimore Ravens), whether they intend on drafting a rookie quarterback or not.
But the Bucs shouldn’t give Winston a shot to increase his value this season, lest they are willing to pay him $20.9 million, which he certainly doesn’t deserve.