Year: 1999
Contract: 7 years, $86 million

As a four-time All-Star and highly touted college recruit, Vin Baker was certainly deserving of his contract. He just didn't live up to it, which makes him as disappointing as anyone else on our list. After signing his contract, Baker's play consistently dropped for three consecutive seasons before being traded to Boston in 2002, where his struggles with alcoholism were revealed.