Kawhi Leonard is back in Toronto, and with the new extension in place, the Raptors are betting that this time can look a lot different from the first go-round.
The upside is obvious. If Leonard stays healthy and the pieces around him and Scottie Barnes fit together, Toronto has a real path into Eastern Conference contention.
That’s the dream scenario. The more immediate question is whether Leonard can actually hold up long enough to get there, because that’s where the concern starts to creep in.
Zach Lowe didn’t exactly sugarcoat that issue on The Bill Simmons Podcast.
“I’m very high on the Raptors as a regular season team,” Zach Lowe said on The Bill Simmons Podcast. “I just don’t know why anyone would expect Kawhi to be able to get through…three playoff series after a functional regular season when..he has not finished a second-round playoff series since 2020.”
That’s the shadow hanging over this move. Toronto can talk about championship ceilings, and maybe that day comes later rather than sooner.
But even a more modest leap would matter a lot. If Leonard can push the Raptors past the first round and get them through a full second-round series, regardless of the result, that would already feel like meaningful progress for both sides.
There’s also a bigger legacy play here for Leonard. Reporting has it that he wants to retire a Raptor, and after the messier chapters of his career - the lack of playoff success with the LA Clippers, the salary-cap circumvention scandal, and his departure from San Antonio - Toronto gives him a chance to end with a fanbase firmly in his corner.
He already delivered a title in 2019 before leaving immediately afterward. If he now helps build another contender around Barnes and the rest of the young core, some of that old resentment could fade. And even if another championship never comes, Leonard still has a shot to rewrite the story of his postseason reputation by finding real playoff success again in Toronto.
From the Raptors’ side, the gamble made sense. They knew the risks attached to Leonard.
They also knew the roster needed a jolt. Adding a superstar scorer and closer was the cleanest way to do it, especially one who can do that without becoming a defensive problem on the other end.
At the very least, Leonard gives Toronto a chance to chase a top seed in the East and make life after the first round. If the team had settled for Brandon Ingram as Barnes’s co-star, the ceiling would likely have been much lower - probably a play-in-level squad sitting behind New York, Philadelphia, Boston, Detroit, Cleveland, Miami, and Indiana.
For a team that finished fifth in the standings even while outperforming expectations, that would have been a step backward. With Leonard, the Raptors at least have a swing worth taking.
In Other News...
Raptors Bench Battle Could Decide More Than Just Final Rotation Spots
The Raptors rotation picture already has some clear pillars, with Kawhi Leonard and Scottie Barnes at the center and a group that includes Immanuel Quickley, RJ Barrett and Jakob Poeltl still working to establish how they fit around them. The real intrigue, though, is coming from the back half of the roster, where Toronto has several younger names and depth pieces competing for a role before the season even settles in.
JaKobe Walter, Collin Murray-Boyles, Jamal Shead, Jamison Battle, Allen Graves and Kyle Anderson are all in the mix for bench minutes, and the fight is about more than just filling out a game-night card. For a team trying to sort out its identity and maximize the edges of the roster, every practice and preseason run carries extra weight, even for players who may end up taking very different paths before they get there. [Read more 🡒]
Kawhi Reunion Could Mean More For Raptors Than A Short Title Push
Kawhi Leonards new two-year, $115 million extension gives Toronto more than just another splashy headline. It gives the Raptors a real runway, with a three-year window to chase a title while keeping Leonard in the fold alongside Scottie Barnes as the organization continues to sort through its roster and figure out the right mix around its core.
The larger significance is what this deal says about Torontos timeline. A player option in the second year gives Leonard flexibility, but it also keeps the partnership alive at least for now, and the Raptors have reason to think bigger than a short push if the fit keeps working. For a team still evaluating how to build a contender around Barnes and Leonard, the next few seasons could tell them whether this is a brief reunion or the start of something longer. [Read more 🡒]
Raptors Enter Camp With One Huge Kawhi Question Looming
Training camp has a different feel in Toronto after the acquisition of Kawhi Leonard from the Clippers, because every move now comes with a championship-sized backdrop. The Raptors are being viewed as contenders for the 2026-27 season, but the biggest early task is figuring out how the new pieces fit around a roster that already had a clear identity.
Scottie Barnes is still the centerpiece, even with Leonard in the mix, and that creates a hierarchy the Raptors will have to manage carefully. There is also a question about how second-year forward Collin Murray-Boyles fits into the picture, while another roster move could still be on the table later in the year if Toronto decides it needs more help closer to the trade deadline. [Read more 🡒]