21. Trading Clyde
Lest you think the Knicks only started to make soul-crushing, head-scratching moves in the 2000s, recall that the team traded Walt "Clyde" Frazier—the coolest player in basketball history. You could argue that the move made sense from a basketball standpoint; Clyde was 31 and on the decline, and the player they essentially traded him for, Jim Cleamons, was 28, and... Actually, you can't even make that argument, not even close. In his first season in Cleveland, Clyde played 51 games, and averaged 16 points and 4 assists. In three seasons in New York, Cleamons played a lot more games, but not nearly as well. Plus, Clyde off the court >>> Cleamons on it.