Jay Cutler

Denver moved Jay Cutler and a fifth-round pick to Chicago after the quarterback relationship deteriorated, receiving Kyle Orton and a package that included two first-round picks and a third-rounder. Denver wrung strong value from an untenable quarterback situation. Cutler gave Chicago legitimate starting-caliber play but never became the franchise-elevating answer the Bears hoped for, while Denver extracted Kyle Orton and multiple premium picks from a broken relationship. The Broncos did not perfectly convert every asset, but the trade return itself was substantial enough to favor Denver in hindsight.

Denver moved Jay Cutler and a fifth-round pick to Chicago for Kyle Orton and a package including two first-round picks and a third-rounder. The Broncos extracted major value after the relationship with Cutler collapsed, but the return was not converted cleanly enough to make this a slam dunk. Chicago got the quarterback stability it wanted for stretches, though not a true franchise breakthrough.