New Orleans Saints
With Drew Brees likely retiring, the New Orleans Saints will have major quarterback controversy this offseason. Taysom Hill is back next season and Jameis Winston is expected to be re-signed as well, but Winston may want to land somewhere else where he won’t have to compete with the coach’s favorite player for the starting job.
Trubisky could be a perfect fit for this team. As he drew (see what I did there?) many comparisons to Brees coming out of college, Sean Payton could be the coach to fix Trubisky. With the offense being based on getting the ball to their playmakers like Michael Thomas, Alvin Kamara, and others, Trubisky is best suited for that.
Additionally, Trubisky would learn from one of the greatest offensive coaches in the NFL. Behind that elite offensive line, Trubisky would virtually never be pressured and would have all the time in the world to practice reading the field. We already saw Payton succeed with both Bridgewater and Hill.