2. Derrick Dockery (7 years, $49 million)
In 2007, the Buffalo Bills made a big splash in free agency by signing Derrick Dockery to a seven-year deal worth $49 million. At the time, it was one of the biggest contracts ever for a guard in the NFL.
Dockery was expected to come in, alongside Langston Walker, and help the Buffalo Bills improve their offensive line. He would go on to start every game over the next two years for the Bills but was released before his third season with the team in an effort to create some cap space.
If Dockery was just evaluated by his play on the field, he wasn’t a bad player and at a minimum was consistent. However, when a player receives that type of contract he is expected to bring more than just consistency. The Bills made Dockery one of the top paid players at his position even though he didn’t show he was that caliber during his time with Washington.
The combination of average play along with releasing him after only two seasons is why this contract is ranked where it is.