The Toronto Raptors have already made one major splash this offseason, and now the conversation is turning to whether they should keep the reunion tour going.
After sending Brandon Ingram, Gradey Dick, and draft picks to the Los Angeles Clippers for Kawhi Leonard, Toronto has reconnected with the player who helped deliver a championship in 2018-19. Leonard is back, but at 35, he is not the same force he once was. That leaves the Raptors with a clear question if they want to push for contention in 2026-27: is one former star enough?
DeMar DeRozan has emerged as the obvious name to watch.
He spent the first nine seasons of his career in Toronto, became one of the franchise’s defining players, made four All-Star teams, and picked up MVP votes twice. He also happens to be the player who was shipped out in the original Leonard deal, which means the two stars never shared the floor in Toronto. Now DeRozan is available after being released by the Sacramento Kings in a cost-cutting move, and he should be looking for a contender.
CBS Sports’ Sam Quinn recently listed the best landing spots for DeRozan, and Toronto was among them. As Quinn put it:
It comes down to how much faith Toronto has in its ability to score when Leonard is on the bench. If the Raptors want to have a spare half-court shotmaker, sure, DeRozan at the minimum is good bang for their buck.
But with Scottie Barnes ascending into true stardom last season, it feels likelier that Toronto just staggers him and Leonard and trusts Barnes to generate their offense when Kawhi rests. It's not out of the realm of possibility, but it's not the cleanest fit either.
That’s the heart of the fit issue. Toronto is already light on shooting, and DeRozan wouldn’t solve that problem. Still, there’s a basketball case for it if the Raptors believe Scottie Barnes can keep taking another step and carry the offense when Leonard sits.
DeRozan would give them a dependable mid-range scorer off the bench, and he’d bring veteran presence to the locker room as well. In 2025-26, he appeared in 77 games for the Kings and averaged 18.4 points, 4.1 assists, and 2.9 rebounds while shooting just under 50% from the field.
He’s not the star he used to be, but he can still score, and he could still give Toronto a lift. If DeRozan wants a return to where it all started, the idea at least has some logic behind it.
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Raptors Reunion With DeMar May Have Been Doomed All Along
The Raptors long-ago pivot to Kawhi Leonard still hangs over any conversation about a DeMar DeRozan reunion, because the idea has always been about more than nostalgia. Toronto has spent years trying to balance star power, lineup fit and the cultural pull that comes with being the citys team, and DeRozans name keeps surfacing whenever the roster looks like it could use another proven scorer. Even the outside chatter has reflected that tension, with some around the league wondering whether the franchises identity, not just its basketball fit, would make a return feel complicated.
Sam Quinn of CBS has argued DeRozan is not the cleanest fit for what Toronto would need now, suggesting the Raptors could instead lean on staggered usage with Scottie Barnes and Leonard to create offense. Drakes presence in the Toronto conversation only adds another layer, since his influence around the team has often been part of the backdrop whenever old Raptors ties come up. For now, the reunion remains more of a debate than a transaction, and the real question is whether the organization ever decides the basketball case is strong enough to override everything else. [Read more 🡒]
Kyle Lowry Day Just Turned Kawhi Leonard's Return Into Pressure
Kyle Lowrys day in Toronto was supposed to be about celebration, and in a lot of ways it was. The franchise retired No. 7 in his honor, giving the longest-tenured face of the Raptors era a proper hometown salute, and Lowry used the moment to look back on the years that made him a fixture in team history. It was the kind of ceremony that reminded everyone how much of the modern Raptors identity was built around his edge, his leadership and the title chase that changed the organization forever.
But the return of Kawhi Leonard has shifted the conversation from memory to expectation. Lowry made it clear the bar is no longer nostalgia, and the front office has been just as direct about the goal now that Leonard is back in the fold. With the 2026-27 season in view, the message around the team is unmistakable: this is about winning another championship, and anything less would feel like a missed opportunity. [Read more 🡒]