19. Kendrick Perkins to the Thunder
Trade: Boston Celtics get Jeff Green, Nenad Krstic, cash, and a 2012 1st Round Draft pick (Fab Melo); Oklahoma City Thunder get Kendrick Perkins and Nate Robinson.
Trades where everyone loses are always sad, but this one takes the cake. Perkins and Jeff Green have both gotten individually worse since the trade, while their teams have generally played well, masking how bad this trade was. OKC traded Green along with a draft pick and cash for Perkins and overpaid Perkins in a four-year, $22 million extension. While Green had to get heart surgery causing him to miss the 2012 season. But Boston believes in him and gave him a four-years, $36 million. Pressure busts pipes, but also makes teams re-sign players at ludicrous prices.