4. Marqise Lee, WR (4 yrs., $38 M)
To say that former Jaguars general manager Dave Caldwell was bad at evaluating talent is an understatement. While he was good at finding diamonds on the rough after the draft (James Robinson, Tyler Shatley, Andrew Wingard), he was pretty bad when it came to deciding which players they should re-sign and which ones they should let walk in free agency.
One of them was Marqise Lee. The 39th overall pick in 2014 was outplayed by teammate and fellow second-round draft pick Allen Robinson. That's right, the Jags drafted two wide receivers in the same round the same year but chose to keep the one that wasn't nearly as productive. Maybe they tried to save money, or perhaps they liked another intangible characteristic Lee brought to the table.
Either way, Caldwell re-signed the wrong wide receiver. While Allen went on to have a productive stint with the Chicago Bears after four years in Jacksonville, Lee peaked in 2017, hauling in 56 receptions for 762 yards with three touchdowns. Still, the Jags gave him a four-year deal worth $38 million the following year and all he had to show for was three receptions for 18 yards.
In Lee's defense, the Jaguars wouldn't have predicted that he would tear his ACL in 2018, effectively shutting him down for the year, and a shoulder injury in 2019 would cut his season short. Either way, the former USC standout didn't turn into the playmaker Jacksonville expected. To nobody's surprise, he was let go in 2020.