4. He’s asking too much
If Winston was an established quarterback who had proven to be a big-time play-maker, he’d easily become the highest-paid QB in the league with this offseason. However, he hasn’t proven that he deserves that money yet.
Winston is going to get a nice contract, but I’m not sure any organization will give him what he wants. The Buccaneers will likely use the franchise tag- if they do choose to bring him back- and that will give Winston a salary of around $27.5 million.
It should be noted that Winston has reportedly said that he’d be “extremely unhappy” if the organization used the franchise tag on him. That difficulty when it comes to negotiation table may be enough for the Bucs to look elsewhere.