2. Jerome James
The Knicks gave James a five-year, $30 million contract in 2005 in one of the worst free agent signings in NBA history. He was not one of the highest-paid players in the league, but James was 29 years old and had never averaged more than 17 minutes per game for a season. The seven-footer got the contract after a strong playoff run with the SuperSonics where he averaged 12.5 points, 6.8 rebounds, and 1.8 blocks per game.
Those 11 games were all it took for the Knicks to offer a massive salary and it blew up in their face. In year one of the contract, James averaged 3.0 points and 2.0 rebounds in 9.0 minutes per game over 45 contests and things got worse from there. He played a total of 90 games over four years with the Knicks before they dumped his contract on the Bulls in 2009 to get Larry Hughes.
It was clear from the start that the deal was not going to work, but the Knicks held on for four and a half years. Even after he played just two games in the 2007-08 season, New York kept him on the roster. They survived another two games played the following year.
Unsurprisingly, the New York Knicks missed the playoffs every year with Jerome James on their roster and they were one of the worst teams in the league during that stretch.