The hottest topic surrounding the Raptors right now is the possibility of Kawhi Leonard returning to Toronto this offseason. Jake Fischer reported that Leonard would be open to signing a long-term deal with both the Spurs and Raptors if he and the Clippers couldn’t agree on an extension.
This idea of the Klaw sounds glamorous, but in reality, Leonard is likely using the Raptors as leverage to show LA there’s interest and force their hand into giving him an extension.
In my eyes, the idea of pursuing Leonard is a pointless one and simply something Bobby Webster shouldn’t pursue. But what about another franchise legend: DeMar DeRozan?
DeRozan, of course, was traded for Leonard in that 2018 offseason and was the Raptors' franchise player for nine years. DeRozan, now 36, isn’t the No. 1 option scorer he once was, but with him potentially being waived by the Sacramento Kings, he would be a great way for Toronto to bolster their second unit.
It’s time to do right by DeRozan
Mike Scotto reported recently that the Kings will likely waive and stretch DeRozan’s $10 million guaranteed over the next three seasons. Scotto also said that if this were to happen, the Clippers were expected to be the favorites to land the six-time All-Star.
While the Raptors weren’t directly linked to DeRozan, the fit makes sense and could be his way of getting a storybook ending to an incredible career. I want to make one thing clear: I’m not at all saying that if Toronto failed in their pursuit of Leonard, they should pivot to DeRozan, as they are in very different tiers of players. I’m just suggesting DeRozan is 100 percent someone the Raptors should target if he is to hit the open market.
This past season, he averaged 18.4 points, 2.9 rebounds, and 4.1 assists per game, shooting 49.7 percent from the field and 32.0 percent from three on 1.9 attempts per game.
In the 2025-26 campaign, the Raptors had a very strong bench unit with players like Jamal Shead, Ja’Kobe Walter, Sandro Mamukelashvili, Collin Murray-Boyles, Jamison Battle, and Gradey Dick. But what they lacked was that killer. They needed someone not only to really lead that second unit, but also to step up, make big shots, and carry the offensive load for portions of the game. Demar can be that.
Now, the immediate red flag with a player like DeRozan, especially for this current Raptors group, is that he can’t space the floor, and this team already struggled with that immensely in 2025-26. He’d be another wing like RJ Barrett and Brandon Ingram, who are primarily inside-the-arc scorers, and that may scare some away from a reunion.
That goes back to a point I’ve hammered home a million times, which is that Barrett is no longer needed on this team.
When you’re paying someone the way Toronto is Barrett, him being a starter isn’t a question, and when he shares the wing position with BI, it makes the team's offense too one-dimensional. So shipping out Barrett for some floor spacing or financial flexibility and replacing him with DeRozan would be brilliant.
Adding Deebo in free agency would come at a fraction of Barrett’s price and help open the door for Ja’Kobe Walter to be the team's starting two-guard next season.
If the Raptors are looking to reunite with former players this summer, DeRozan should take priority over Leonard, unlike the 2018 offseason. At his age, DeRozan has continued to show he can be a healthy (played 74+ games over the last five years), reliable bucket-getter who is exactly what Toronto’s second unit has been craving. Bobby Webster can improve both the Raptors' second unit and give DeMar DeRozan the send-off he never got the first time with a reunion this summer.
Seems like a no-brainer to me.
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