12 Players the Raptors never should have gambled on

5. Jerryd Bayless

The Raptors made a regrettable trade in Nov. of 2010 as they shipped out Jarrett Jack and two role players for Bayless and Peja Stojakovic. Jack was the team’s starting point guard, but Toronto was ready to move on after Chris Bosh departed for Miami in free agency. They got Stojakovic, who lasted just two games with the Raptors before being waived only for the 6’10 forward to play a key role on the Mavericks title squad later that season.

Bayless was the prize of the deal for Toronto, but he was primarily the backup point guard behind Jose Calderon. The 6’3 guard had flashes of brilliance and plenty of head-scratching moments during his season and a half with the Raptors. He had two 30-point games and 18 times where he scored two or fewer points.

Bayless was never short on confidence, and it was clear that it was time to move on. An oblique injury limited him to just 31 games in the 2011-12 season, and the Toronto Raptors let him walk in free agency the following offseason. They were ready to get off the roller coaster ride that was the 6’3 guard’s play.

Giving up Jarrett Jack to get Jerryd Bayless was a regrettable move for the franchise. Over the next five years, Jack averaged 12.2 points and 5.2 assists in 29.7 minutes per game as his team made two playoff appearances. Bayless produced 9.1 points and 3.1 assists in 23.6 minutes per game but was the Grizzlies’ backup point guard during their 2013 run to the conference finals.