Greg Olsen
This is probably the one that Bears fans are up in arms about the most. No surprise since it’s the most recent. The reasoning at the time that Greg Olsen was traded to the Carolina Panthers was due to offensive coordinator Mike Martz. His scheme didn’t have much use for receiving tight ends. So rather than tell him to find a way to make due, considering Olsen was fairly productive anyway, the Bears dealt him for a third round pick.
Easily one of the biggest steals of the past decade for Carolina. Olsen has become their primary weapon in the passing game. He has posted over 1,000 yards in each of the past three seasons alone and reached three Pro Bowls. In the most bitter twist of fate, Martz was fired following the season that trade was made in 2011. The only thing the Bears salvaged was packaging that pick in a deal to get Brandon Marshall in 2012.