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

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. 

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.