8. Jermaine O’Neal
The Raptors were coming off back-to-back first-round playoff exits when they traded the 17th overall pick in the 2008 draft, T.J. Ford, Rasho Nesterovic, and Maceo Baston for O’Neal and the 41st selection. It was a massive gamble, but Bryan Colangelo dreamed of Bosh and O’Neal being the perfect frontcourt pairing that pushed Toronto to new heights.
The six-time All-Star lasted just 41 games with the Raptors. He was starting to decline but still produced strong numbers as he averaged 13.5 points, 7.0 rebounds, and 2.0 blocks in 29.7 minutes per game. The frontcourt fit was not ideal and the Raptors were near the bottom of the Eastern Conference standings when they traded O’Neal to Miami in February. It cost them two draft picks and Jamario Moon to get Shawn Marion and Marcus Banks.
Jermaine O’Neal played five more years in the NBA before retiring in 2014. His time with Toronto was certainly forgettable, but it was just the beginning of a rough stretch for the Raptors. Chris Bosh left in free agency in 2010, and the franchise missed the playoffs five straight years.
Toronto Raptors fans are more scorned by this trade because the Pacers selected Roy Hibbert with the 17th pick, who was arguably a better fit next to Chris Bosh and could have changed things in Toronto.