2. Julius Thomas, TE (5 years, $46 M)
Before inking (and later re-signing) Evan Engram, the Jaguars haven't been known for their tight end play. Sure, Kyle Brady had his moments, and Marcedes Lewis was a mainstay of their offense for more than a decade. However, not many of their tight ends enjoyed name recognition. They expected to change that when they signed Julius Thomas to a monster contract worth $46 million in 2015.
A former Hoops player, Thomas was coming off a pretty successful two-year stretch with the Denver Broncos. Having hardly played in 2012, Thomas enjoyed a surge the next two seasons, hauling in 108 receptions for 1,277 yards with 24 touchdowns. Dave Caldwell — you will see his name pop up often in this article — thought (wrongly) that the Jags could use that kind of production.
The issue is that Thomas didn't come with Peyton Manning, the quarterback who made him look great, and padded his stats in Denver. Another thing Caldwell failed to take into account was that Thomas wasn't a top target in their passing game. Instead, he was often the fourth or fifth option on the Broncos offense behind Wes Walker, Eric Decker, and the late Demaryius Thomas. Last but not least, Thomas would be catching passes from * checks notes * Blake Bortles, not one of the best ones ever to play quarterback in NFL history.
To nobody's surprise outside of Caldwell, Thomas struggled in a more prominent role and tried to get a hold of Bortles' floaters. The Jags tried to make things work out but they cut their losses after two unsuccessful years. Thomas was traded to the Miami Dolphins before calling it quits. Then again, he didn't have to work ever again after getting that one big paycheck from the Jaguars.