7. Carmelo Anthony
The ten-time All-Star and member of the NBA 75 squad may be a surprise addition to this list, but the Knicks gave up four players and four draft picks to acquire him in February of 2011. They traded him away in 2017 for two fringe role players and one second-round draft pick, which sounds like the definition of hanging on too long.
Beyond that, the Knicks paid Carmelo $147.4 million over seven years for three playoff appearances and one trip to the second round. New York won 117 games over the final four years combined with Anthony, and it started a seven-year playoff drought for one of the NBA’s all-time great franchises.
Carmelo continued to produce outstanding numbers throughout his tenure in New York. He was an All-Star every year and never averaged fewer than 21.8 points per game, but the Knicks did not win. Blame Anthony. Blame the front office. Blame his supporting cast. It does not matter. Things simply did not work. Teams acquire superstars to compete for championships, and the Knicks never did that with Carmelo Anthony, despite paying him like one of the league’s elite players.
The 6’7 forward’s production immediately dropped off after leaving the Big Apple, and he quickly became a bucket-getting role player over the final four years of his NBA career.