2. Hakeem Olajuwon
Olajuwon is an all-time great and one of the best centers in NBA history. The 12-time All-Star led the Rockets to two championships as he twice led the league in rebounds and made nine All-Defensive teams. The Dream was no longer an elite big man when he arrived in Toronto, but nobody expected the sign-and-trade to completely blow up in the Raptors’ face.
Olajuwon got a three-year $17.4 million from Toronto as a 38-year-old in 2001. Vince Carter was in his prime, and the Raptors had made two straight playoff appearances. They thought The Dream could help them get over the hump, so they gave the Rockets two draft picks, including a first-rounder for the future Hall of Famer.
Olajuwon only played one season with the Raptors where he averaged a career-low in points, rebounds, and blocks per game. He was clearly past his prime and only able to play 22.6 minutes per game. The Dream struggled mightily in the playoffs as the Raptors exited in the first round. Those would be his final games as a back injury forced him to retire in 2002.
The Toronto Raptors dreamed of having an elite defensive anchor that could help push them to the next level, but Hakeem Olajuwon did not have enough left in the tank. The three-year deal turned into a disaster and one that haunted the franchise as they began a rebuild in 2002.