3 times the Raptors bombed in free agency, and 2 times they reaped the rewards

2012: Landry Fields (three-year, $20 million)

Some of you may know Landry Fields as the front office exec who continuously seems to be making questionable moves for the Atlanta Hawks this offseason – but once upon a time Landy Fields was the future of the New York Knicks and even had Spike Lee wearing his jersey courtside at Madison Square Garden.

After being drafted 39th overall by the Knicks in 2010, Fields instantly became a fan-favorite in New York and finished fourth in Rookie of The Year Voting. After experiencing a slight sophomore slump in year two, Fields was eligible for free agency and signed an offer-sheet with the Toronto Raptors – a team who was looking for a consolation prize after losing out on the Steve Nash sweepstakes.

Many Raptors fans were intrigued with the signing – Fields was a 3-and-D player who at best could return to his rookie year success, or at worst compliment DeMar DeRozan as a kick-out option.

Well there was an option that wasn’t being considered for the 24-year-old forward – losing his ability to shoot the ball.

Fields suffered an extremely rare nerve injury in his shooting elbow which caused him to miss a lot of shots (and a lot of time) playing in only 107 games throughout the span of his three-year deal. Sadly for Fields, the elbow never truly healed and those three years would be his last as a player in the NBA. 

2015: DeMarre Carroll (four-year, $60 million)

I’m going to give Raptors President Masai Ujiri the benefit of the doubt on this one and assume he was trying to forecast the salary cap jump that led to an infamous 2016 free agency – but this deal still made very little sense from the get go.

After back-to-back career seasons for DeMarre Carroll, the 29-year-old forward hit free agency as the best 3-and-D option playing for a 60-win team in the Atlanta Hawks. The Raptors were coming off two straight first-round exits and were looking to add a third option behind DeMar DeRozan and Kyle Lowry and Carroll’s defensive identity was a perfect fit for Dwane Casey’s system.

Well, not really.

Carroll was already rehabbing a knee injury the summer he signed the deal, and only appeared in 26 games for the Raptors in 2016. Despite holding his own on the defensive end, Carroll struggled to mesh with the Raptors offensive system and produced a negative plus/minus on the offensive end in both seasons with the team.

The Raptors eventually traded Carroll as a salary dump to the Brooklyn Nets halfway through the deal, and had to attach draft compensation to make it happen.