Toronto never really stopped talking about Kawhi Leonard. The city just lowered the volume.
Now, seven years after delivering the Raptors their only NBA championship, Leonard’s second chapter in Canada is already moving from reunion headlines to real business. The Raptors and Leonard are expected to begin extension talks this week, and according to the reporting by ESPN’s Shams Charania, the two-time Finals MVP will enter those conversations with new representation after hiring Harrison Gaines, Esq. of SLASH Sports as his new agent.
Kawhi Leonard and the Toronto Raptors are expected to start extension talks this week — and the two-time Finals MVP will do so with new representation. Leonard has hired Harrison Gaines, Esq. of SLASH Sports as his new agent.
ESPN Story: https://t.co/5n0D0vR4dJ
— Shams Charania (@ShamsCharania) July 6, 2026
That is not a small detail. Leonard’s return to Toronto was always about more than nostalgia. Yes, the memories are obvious: the 2019 title run, the Game 7 bounce vs Philly, the Finals MVP trophy, and one of the most unforgettable one-year stays in modern NBA history. But this move only truly makes sense for the Raptors if it comes with commitment beyond a single season. Toronto paid a real price to bring him back, reportedly sending Brandon Ingram, Gradey Dick, two future first-round picks, two second-round picks and a pick swap to the Clippers. That is not a “welcome home” gift basket. That is a franchise pushing its chips back toward the middle of the table.
Leonard, 35, has one year left on his current deal, and the extension conversation is expected to center around a two-year framework that could keep him in Toronto through the 2028-29 season. The number attached to that possibility is massive, reportedly placing the potential extension as high as $123.7 million. For a player with Leonard’s résumé, that price is not shocking. For a player with Leonard’s injury history, it is still a serious bet.
That is the entire Kawhi equation in 2026. When he is right, he remains one of the sport’s cleanest playoff weapons: high-efficiency, surgical in the midrange, strong enough to punish switches and smart enough to never rush the moment. Last season with the Clippers, he reminded the league that the superstar version is not just a memory, averaging 27.9 points, 6.4 rebounds and 3.6 assists over 65 games. Toronto did not trade for a museum piece. It traded for a closer.
The Gaines angle makes this even more interesting. Harrison Gaines is not one of the industry’s anonymous power brokers, but he is not walking into the room blind either. SLASH Sports presents itself as a full-service representation firm for NBA, WNBA and NIL clients, and Gaines’ own background includes prior involvement in major contract work tied to Leonard earlier in his career. In other words, this is not simply a new agent picking up the phone. It is a familiar basketball-business connection resurfacing at a very important moment.
For the Raptors, the pitch is obvious. Leonard already knows what Toronto can be when the building is shaking, the defense is connected and the city believes. He also joins a team that is no longer rebuilding from scratch. Scottie Barnes gives Toronto a younger franchise pillar. Immanuel Quickley and RJ Barrett provide creation and pace. Collin Murray-Boyles adds defensive bite. Leonard gives all of that something it badly needed: a playoff possession solver.
For Leonard, the pitch may be even cleaner. In Los Angeles, the Clippers era never became what it was supposed to become. There were flashes, big expectations and plenty of talent, but injuries and roster turnover kept interrupting the story. Toronto offers something different: a place where he is already immortal, a franchise that has reorganized itself around his return, and a chance to turn the most famous rental in NBA history into something more permanent.
