Eight years later, the Kawhi Leonard gamble still sits at the center of everything the Toronto Raptors built.
The franchise’s biggest trade ever sent DeMar DeRozan, Jakob Poeltl and a 2019 first-round pick to the San Antonio Spurs and brought back Leonard and Danny Green. It was a stunning move at the time, especially with Leonard carrying just one year left on his contract. But Toronto was staring at a closing window after playoff exits in 2016, 2017 and 2018, and Masai Ujiri made the hard call to shake the roster up.
The payoff came fast. Leonard gave the Raptors the kind of two-way force they needed, and the team was better suited for the postseason because of it. Less than a year after the trade, Toronto won its only NBA championship.
One moment from that run still defines the deal. In the second round against the Philadelphia 76ers, Leonard drilled one of the wildest game-winners the league has ever seen, a shot that bounced around the rim multiple times before finally dropping through.
The risk was obvious from the start. Leonard was never planning to sign a long-term extension in Toronto, and after the title run he left in free agency for the hometown Los Angeles Clippers, where he had always wanted to play.
Now the story has come full circle. After seven years with the Clippers, Leonard is again on the move, with one year left on his deal and a willingness to extend only in Toronto. That possibility only exists because of what happened in 2019, and the Raptors may be positioned to turn that old championship swing into something new.
On June 30, Toronto agreed to a trade with the Clippers that would have sent Brandon Ingram, Gradey Dick and multiple first-round picks to Los Angeles, but the deal has been paused until the investigation regarding the Clippers' alleged salary cap circumvention is complete.
If Leonard ends up back in Toronto, the fit makes sense on the floor too. His defence would line up well alongside Scottie Barnes and Collin Murray-Boyles, while his presence could ease some of the offensive burden on Immanuel Quickley and RJ Barrett.
It’s rare for one trade to shape two championship eras, but that’s the path Toronto could still be walking.
In Other News...
Raptors Offseason Still Hinges On Kawhi As Camp Nears
The Raptors have spent much of their offseason waiting on a deal that has become as much about timing as basketball, with Kawhi Leonard still in the middle of an investigation into alleged salary cap circumvention tied to the Clippers. The review, being handled by Wachtell, Lipton, Rosen & Katz since September, has hung over the process long enough to add real uncertainty to Torontos plans, even as the club has shaped its summer around the possibility of a trade getting done.
Training camp is now close enough that the stakes feel more immediate, but the path forward remains unclear. Leonards situation is still unresolved, the investigation has introduced complications at every turn, and the Raptors cannot count on the move being completed even though it has been central to how they have approached the offseason. [Read more 🡒]
Former Knicks Big Man Now Has Something To Prove In Toronto
Toronto is taking a low-risk swing on its frontcourt by bringing in Trey Jemison III, a center with three years of NBA experience who has bounced around a few different teams and now gets another chance to carve out a role. The move adds some needed depth at a position where teams are always looking for size, rebounding and a little stability, and Jemison arrives with the kind of rsum that suggests he has already seen enough to understand how quickly opportunities can disappear.
For Jemison, the appeal is simple: the Raptors are offering a path, and he gets to show he can fit into a rotation that values effort and functional interior play. His most recent stop came with the Knicks, and while this next chapter does not guarantee anything, it does put him in a spot where a strong impression could matter in a hurry. [Read more 🡒]
Raptors Christmas Day Snub Suddenly Feels Bigger Than The Schedule
The Raptors absence from the NBAs 2026 Christmas Day slate landed as more than a simple schedule note, especially for a franchise that has spent enough time in the leagues holiday spotlight to know what being left out can signal. Toronto has a history with Christmas games, and when the league builds one of its showcase dates without them, it naturally invites a closer read on where the team sits in the NBAs broader picture.
Kawhi Leonards ongoing investigation only adds another layer to the conversation around that omission, even if there has been no official confirmation of any punishment. The possibility of a suspension hanging over Leonard has made the Raptors early-season status feel suddenly more precarious, and it is hard not to wonder how much of that uncertainty could still be lingering when the holiday games arrive. [Read more 🡒]