4. LaMont Jordan, RB, New York Jets
LaMont Jordan turned a four-year stint as a backup on the New York Jets in to a five-year, $27.5 million with Raiders before the 2005 season. Initially the contract looked like a steal as Jordan had his first 1,000 yard season and led all running backs with 70 receptions. He lead the Raiders with 11 total touchdowns and looked like he could be the Raiders lead back for the length of his contract. The 2006 season started off well for Jordan but in November he tore his MCL and missed the rest of the year.
After the injury Jordan lost his starting job to Justin Fargas and was never quite the same player. Jordan still managed to rush for 549 yards in his final year with a Raiders in a reduced role, but he was certainly not the player Al Davis expected him to be after giving him that five-year deal. Perhaps if he had not gotten injured then he could have continued to be the feature back he was paid to be, but health is always a factor when judging the value of a player and his contract.
Jordan was released and played another two years in the league as a backup in New England and Denver but as is typical of NFL running backs, lost his burst and found himself out of the league shortly after his 30th birthday.