Khalil Mack

The Chargers acquired Khalil Mack from Chicago for a 2022 second-round pick that became Jaquan Brisker and a 2023 sixth-round pick. Mack delivered real pass-rush production for Los Angeles, but the Bears moved an expensive veteran contract and landed a young defensive starter. Chicago gets the slight hindsight edge on value and roster timing.

Chicago's trade for Khalil Mack gave the Bears an instant superstar and briefly turned their defense into one of the league's defining units. The Raiders received a major draft package, but the return never matched the value of an elite pass rusher in his prime. Chicago paid heavily, yet still acquired the best player. The deal remains a strong Bears win because Mack delivered superstar impact immediately, even if Chicago did not turn the window into a championship.