5. Jameis Winston
Jameis Winston’s future with the Buccaneers remains in flux as we near the start of free agency. Like several teams, Tampa Bay has been linked to Tom Brady and its potent young offense. Ultimately, if Brady were to land with the Bucs, Winston’s future in Tampa would effectively come to an end.
It’s believed that should Winston leave Tampa that he wouldn’t become an immediate Day 1 starter with his new team. So given the Bears want to give Mitchell Trubisky one more chance to prove that there’s something worth salvaging, bringing in a talent like Winston with a slew of upside but someone that won’t be handed the starting job over Trubisky could work in Chicago’s favor. Again, if Trubisky struggles, the Bears could turn to Winston without a concern.