
25. Jay Cutler
Cutler never became the bonafide franchise quarterback Chicago expected. The Bears traded for him in a complex blockbuster deal in 2009. The Broncos were happy to move on after the arrival of Josh McDaniels. Meanwhile, Cutler believed he was a perfect fit for the Windy City. In the end, the Bears just treaded water for a few years (via USA Today).

This three-way trade saw the Broncos receive Kyle Orton and multiple picks. Cutler had a mediocre first season in Chicago as they missed out on the playoffs. However, he improved the following year and the Bears won the NFC North. Then a thumb injury affected him and he never properly recovered. It’s a tale of what could have been for the franchise.