15. Jay Cutler (2017)
Cutler played for eight years as the Chicago Bears’ QB. However, they only made the postseason once during this era (via New York Times). Finally, the Bears decided to go in a different direction and brought in Mike Glennon from Tampa. After a 3-13 season, the writing was on the wall for Cutler but things didn’t exactly get better for Chicago.
Glennon was shambolic for the Bears and still sends shudders down the spines of their fans. To be fair, Cutler only played in five games in his final season because of injuries. He retired but returned when the Miami Dolphins desperately reached out to him. Cutler enjoyed his final year as an NFL starter before he went off into the sunset.