Jim McIlvaine: 7 years, $33.6 million (1996)
The old saying in the 1980’s and 1990’s was that if you were seven feet tall and could walk and chew gum at the same time, some NBA team was going to hand you a large contract. Just look at center Jim McIlvaine, who averaged less than 15 minutes per game with the Washington Bullets during his first two seasons in the NBA.
But when he became a free agent in 1996, the Seattle Supersonics signed him to a seven-year, $33.6 million free-agent contract. That deal effectively destroyed a really good Seattle team, as it led to acrimony between Shawn Kemp (who was jealous of McIlvane’s deal) and the Supersonics’ front office.