6. Signing Allan Houston For 6 Years and $100 Million
Allan Houston was a very good player, even helping the Knicks reach the NBA Finals in 1999 as one of the team’s core players. After the 2001 season, James Dolan extended Houston with a six-year deal worth $100 million. These types of deals are uncommon for most teams not owned by James Dolan: After two solid seasons, the aging Houston fell to injuries, and didn’t play the final two seasons of his contract — earning $39.5 million without stepping on the floor once.