With the 2024 NBA Draft now in the books, fans turn their heads to what is arguably the most entertaining part of the NBA offseason – free agency. Player movement is higher than ever before and we’ve already witnessed three future hall-of-famers find new homes in Paul George, Chris Paul, and Klay Thompson.
Were the Toronto Raptors ever in the mix? No, not really – but with salary cap complications from a team with a rebuilding perspective, the Raptors are most likely not after the headline names this summer. Let’s take a look back at five times the Raptors invested in a notable free agent and how the deal eventually turned out.
2009: Hedo Turkoglu (five-year, $53 million)
Of course when discussing the Toronto Raptors and free agent signings, we have to start off with the biggest name they’ve signed – and by far the most regrettable deal.
After an extremely disappointing 2008-09 season where the Raptors finished 33-49 despite acquiring six-time All-Star Jermaine O’neal during the summer prior, GM Bryan Colangelo decided to give it another try but this time on the free agent market.
Turkoglu had seemingly already made up his mind after reports came out saying there was a deal in place with the Portland Trail Blazers. Now whether it was the prospect of playing with Chris Bosh (or maybe just a lot more money), the Raptors were able to convince Turkoglu to instead ink a deal with Toronto on a five-year pact.
Initial thoughts on the deal were extremely positive – Turkoglu was coming off an NBA finals run as the second-option for the Orlando Magic, and chose Toronto over many other suitors giving fans hope for a deep postseason run.
But of course the Toronto Raptors of the mid-to-late 2000’s were simply not allowed to have nice things. Turkoglu struggled throughout the season, was allegedly found partying after he skipped a game because of an illness, and requested a trade out of town by bluntly stating “I do not want to go back to Toronto” during an interview.
This was supposed to be the deal that not only changed the Raptors trajectory with Chris Bosh, but also the narrative of free agents not wanting to come to Toronto – it miserably failed at solving both.
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.
2005: Jose Calderon (three-year, $7 million)
Now that we got all of that free agency frustration out let’s focus on some of the positives – and yes there actually were some positives for the Raptors in 2005.
Toronto was looking for a point guard they could plug into their rebuild after a yearly carousel of Alvin Williams, Jalen Rose, and Rafer Alston, and decided to sign Jose Calderon – a 24-year-old point guard out of the EuroLeague.
Despite Calderon’s rookie season struggles, the Spaniard turned out to become one of the best pure shooters in Raptors history. Calderon joined the 50-40-90 club in 2008 and set the record for the highest free-throw percentage during the very next season. Calderon was the team’s starting point guard during the Raptors back-to-back postseason appearance from 2006-2008 and played 525 games in Toronto before being traded to the Detroit Pistons in 2013.
The Raptors eye for international talent hasn’t always worked out (especially in the draft), however Calderon’s deal with the Raptors turned out to be one of the best-value deals for the franchise and quite possibly the only positive from the Mike Babcock era.
1999: Dell Curry (three-year, $6 million)
This is a deal that doesn’t get talked about enough (possibly because it was 25 years ago) but before Steph Curry dominated the NBA, his father Dell was a household name across the league that joined the Raptors in free agency.
Curry was a dominant three-point specialist who is best remembered for his ten seasons with the Charlotte Hornets. After playing the 1998-99 season with the Milwaukee Bucks, Curry had reportedly agreed to return to the Bucks on a two-year extension before Raptors GM Glen Grunwald stepped in with a bigger offer.
The 35-year-old played a vital role as a veteran leader towards the young core of Vince Carter and Tracy McGrady, and served as a valuable shooter off the bench during his time in Toronto which included a trip to the postseason in all three seasons.
