Raptors urged to bring another former star back to pair with Kawhi Leonard

The Toronto Raptors made one of the boldest moves of the 2026 offseason so far. 

The team packaged Brandon Ingram, Gradey Dick, and some draft picks and sent them to the Los Angeles Clippers for star wing Kawhi Leonard. Of course, Leonard spent the 2018-19 season with the Raptors and led the team to a championship. It was also arguably the best season of Leonard's career, so why not run it back? 

Leonard is now 35, though, and not quite the player he once was. As a result, the Raptors probably need to add another piece or two if they plan on contending in 2026-27. Why we're having reunions, though, why not have one more? 

Raptors could reunite with DeMar DeRozan

When you think about players who have played for the Raptors, DeMar DeRozan is definitely one of the first names that comes to mind. The California native spent the first nine seasons of his career with the Raptors, earning four All-Star selections and receiving MVP votes twice. 

Ironically, DeRozan was sent out in the original trade to bring Leonard to the Raptors, so the two never played together. However, DeRozan was recently released by the Sacramento Kings in a cost-cutting measure, and should be looking to join a contender. 

Sam Quinn of CBS Sports recently identified the best landing spots for DeRozan, and naturally, the Raptors made the list. Regarding this possibility, Quinn offered the following: 

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.

As Quinn mentioned, the Raptors aren't the most natural fit for DeRozan. The Raptors are already thin on shooting, and DeRozan wouldn't exactly help that. 

However, it's also possible Scottie Barnes takes another step forward and is more than capable of leading the offense when Leonard rests. DeRozan can still be a reliable mid-range shooter off the bench and he'd be a welcomed veteran presence in the locker room. 

In 2025-26, DeRozan played in 77 games for the lowly Kings and averaged 18.4 points, 4.1 assists, and 2.9 rebounds. The veteran wing was one of the few shotmakers on the Kings last season, but he was pretty efficient still, shooting just under 50% from the field. 

DeRozan isn't the star he once was, but he can get some buckets off the bench and excite the Toronto crowd. If DeRozan is interested in a homecoming, it makes some sense. 

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