At the moment, there are so many uncertainties regarding Kawhi Leonard. He could start the regular season as a Toronto Raptor, be a member of the LA Clippers, have his contract voided, be suspended for an extended period, and so much more. The possibilities are quite literally endless, and it’s due to the investigation he is under for alleged cap circumvention off the court.
However, if the Clippers’ trade with the Raptors is successful, and Leonard officially makes the move back to the city where he won his second championship, an extension is expected to be signed, according to Jake Fischer of “The Stein Line.” This is exactly what he wants, as he’ll have a secure future and a prime shot at winning a ring in Toronto throughout the years ahead.
For context, Leonard is currently on a $50.3 million contract that expires after the upcoming season.
Kawhi Leonard is likely hoping the trade goes through more than anyone
Because Kawhi Leonard is 35 years old and entering the later stages of his career, there aren’t many teams outside of the Toronto Raptors who are willing to have him on the books long term. He’s aging, injury-prone, and probably demanding a lot of money that could be spent in other directions.
That makes sense. Had Leonard been in the midst of his prime, there would be a line out the door of teams eager as can be to acquire him in some way, shape, or form.
As a result, among everyone involved in the trade and investigation Leonard is under, he is probably the one hoping everything goes through successfully with no hiccups.
The Raptors were one of his preferred destinations, and despite everything, he found a way to land himself there.
Beyond that, though, is retirement, which is not far away for Leonard. Like many other superstars, he wants to end his career in a meaningful way, and according to Shams Charania, Toronto is where he would like to call it quits.
Kawhi Leonard reportedly wants to retire as a member of the Toronto Raptors once his career comes to an end, per ESPN’s @ShamsCharania. pic.twitter.com/VoI7yp6Ccz
— TSN (@TSN_Sports) June 30, 2026
Why? Well, he won the Raptors’ first-ever championship in just one season spent with the team, and likely enjoyed the way the city treated him.
That said, if the trade doesn’t go through, Leonard will be disappointed. The level of that could vary based on the punishment, but he will not have gotten what he wanted in the offseason before entering an expiring contract year.
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