1. Hedo Turkoglu
Turkoglu was a first-round draft pick in 2000, but it wasn’t until he arrived in Orlando in 2004 that he broke out. The 6’10 forward quickly became a starter and key contributor as the Magic became a force. They reached the NBA Finals in 2009 with Turkoglu as their third-leading scorer and top playmaker in the postseason.
The 30-year-old became a free agent after that run, and the Raptors were eager to improve their roster as they tried to convince Chris Bosh to stay. It resulted in a four-team sign-and-trade that brought Turkoglu to Toronto for Shawn Marion, Kris Humphries, Nathan Jawai, and one second-round draft pick. The newest Raptor also got a fresh five-year $53 million contract, which instantly turned into a disaster.
Turkoglu’s production dropped off across the board as the Raptors missed the playoffs for the second straight year. The 6’10 forward quickly asked to be traded, and he was sent to the Phoenix Suns for Leandro Barbosa and Dwayne Jones just one year after arriving in Toronto.
The Toronto Raptors quickly regretted signing Hedo Turkoglu, and matters quickly went from bad to worse when Chris Bosh left in free agency in 2010. It was one of many unfortunate moves by the team’s front office. Who will be the next player to make this list? Stay tuned to find out.