2. Jameis Winston would be an interesting backup for a rookie quarterback
If the Chicago Bears signed Jameis Winston, it would be a sign that they are drafting a quarterback. First, Winston does not have a playing style close enough to Justin Fields to make sense. More than that, when you draft a rookie quarterback, you want to put him in a spot where he does not have to start day one, but he also has the chance to start day one.
If the rookie is not ready, they can lean on Winston, but even Winston knows he is not the long-term answer wherever he signs this offseason. If he can handle mentoring a young quarterback, the fit would be great.
1. The Chicago Bears could improve their defensive line depth in free agency
One last name to keep an eye on is Malcolm Roach. He is a depth defensive line option with 1,033 snaps in four years. Last year, he played 290 snaps and had arguably his best season. Still, he will not sign for much and will sign to be depth. The Bears are losing Justin Jones, but expecting Gervon Dexter and Zacch Pickens to play more. So, Roach can fill the hole without having to take all of his snaps. This could be a nice match in free agency.