1. Eddy Curry
Curry was the fourth overall pick in 2001, and he steadily improved in his first four years with the Bulls before being traded to the Knicks in 2005. A possible heart problem was at the center of the sign-and-trade, but the Knicks gave up three players and four draft picks, including two first-rounders to get Curry, Antonio Davis, and a first-round selection in return.
The Knicks hoped Curry would continue improving, but it did not happen. The seven-footer had the best year of his career in New York where he averaged 19.5 points and 7.0 rebounds in 35.2 minutes per game, but his production quickly dropped off. Injuries, conditioning, and playstyle issues helped him go from a promising prospect to virtually out of the NBA in three years.
The Knicks could have received a significant haul for Eddy Curry after the 2006-07 season, but he was ultimately salary dumped and waived in 2011. It was a stunning fall that made his six-year, $60 million contract with New York one of the worst in league history.
The New York Knicks handed out a lot of regrettable contracts in the 2000s as the franchise became a laughingstock. They appear to be getting back on track, but the Knicks must learn from the past that hanging onto a player for too long can certainly set the franchise back.