Joe Smith: 1 year, $1.75 million (1998)
Joe Smith never really lived up to the hype of being the #1 overall pick in the 1995 NBA Draft. But Smith found a home in Minnesota, playing alongside superstar Kevin Garnett. But Smith’s contract extension in 1998 will go down as one of the worst in NBA history, not because of the amount, but because of the damage it caused to the franchise.
Smith and the Timberwolves agreed in an illicit deal where Smith signed a deal “below market value,” so the team could acquire some other players in the short term, with the promise of getting paid later. The league fined the Timberwolves franchise $3.5 million, but more severely, it took away five first-round picks. That destroyed the future of the team.