
26. Khalil Mack
Mack is one of the best defensive players of his generation. It’s a shame that he hasn’t played for a franchise that maximized his talents. For some reason Jon Gruden didn’t want him and traded him to the Bears in a blockbuster exchange. This was a massive trade that saw Oakland receive a pair of first-round picks amongst others (via NBC Sports).

Chicago gave up a lot of draft capital in their pursuit of Mack. Meanwhile, they even made him the highest-paid defensive player ever at the time. However, it’s debatable who won this deal. The Bears failed to make the most of their truly elite talent. He put in Pro Bowl performances but the rest of the team didn’t step up. Finally, he changed teams again in 2022 when the Chargers acquired him.