8. Vin Baker

Year: 1998
Contract: $87 million/Seven years
Team: Seattle SuperSonics
After putting up All-Star stats (19 points and eight rebounds per game), the Sonics rewarded Baker with one of the biggest contracts in the league at the time. Baker rewarded them by only playing in 34 games in the first year of his contract. The remaining years would be plagued by his battles with the bulge and the bottle before he was traded to the Celtics in 2002.