I'm just making a case for why it could happen. What people are failing to think about is what other teams may already be making a play for Winston even while the Bucs are deciding. And I think the Patriots could be one. And the Patriots for their part have a business to run, a business of winning championships. They can't sit on their hands and wait around to see if they can squeeze another year out of Old Man Brady.
1) Brady has the power now, but is it the power to get the highest contract? Don't he and his wife have over half a billion dollars or so? What's the difference to him between 25 or 30 or 35 mil? He wants another shot at a title, and that's what he needs to work out. Who can give him the best shot at doing that? Otherwise why keep playing?
2) As Brady thinks about maybe leaving home, he may see the parents already cleaning out his bedroom. Belichick is not patient in these matters. He is very willing to move on from anybody. He also knows his team needs new blood, and keeping Brady around may not serve any purpose, because they aren't going to win a Superbowl in 2020. Should the Patriots try to hang onto the last threads of the bygone past, or is he going to move forward? He needs a QB with leadership skills and experience who can stick around a few years. That basically leaves two guys: Bridgewater and Winston.
3) And for Winston's part, if he's not feeling unconditional love in Tampa, and he isn't, then why not go to a championship caliber organization? He doesn't want to have a legacy of failure.
When you have quarterbacks doing musical chairs, its not just the Bucs sitting back and making their decision. The other teams need quarterbacks too and Winston may not be just a consolation prize for the team that doesn't find a seat.
That's why unless the Bucs tag Winston, and I hope they don't, he may be gone...to the Patriots.
So be amazed, but don't be shocked if Winston ends up in New England. It will be quite the storyline for 2020 to see what happens if Winston is the next QB of the Patriots.