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Mind-boggling Jaylen Brown trade raises questions about Raptors’ Kawhi Leonard move

That’s all the Celtics could get?
May 2, 2026; Boston, Massachusetts, USA; Boston Celtics guard Jaylen Brown (7) on the court before game seven of the first round of the 2026 NBA Playoffs against the Philadelphia 76ers at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images
May 2, 2026; Boston, Massachusetts, USA; Boston Celtics guard Jaylen Brown (7) on the court before game seven of the first round of the 2026 NBA Playoffs against the Philadelphia 76ers at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images | IMAGN IMAGES via Reuters Connect

The Raptors seized an opportunity to build on last season’s success and give Scottie Barnes the co-star he so desperately needs with a Kawhi Leonard reunion that cost them Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, second-round picks in 2030 and 2033, and a 2027 pick swap. It’s not a bad price considering that Leonard is a clear upgrade over Ingram, Dick fell out of the rotation this season, and they have a much higher playoff ceiling now. 

Then, the Boston Celtics went ahead and traded Jaylen Brown to the Philadelphia 76ers for 36-year-old Paul George, 2028 and 2031 first-round picks, and second-round picks in 2028 and 2030. That’s not a great return for a player who just averaged 28.7 points per game in a 56-win season for the Celtics and helped lead them to a title two years ago as the Finals MVP over Jayson Tatum. The move prompted Bill Simmons to question how much it cost the Raptors to get Leonard. 

“How does Jaylen go for half as much as mid-thirties Kawhi, right?” Simmons said on the July 2 episode of The Bill Simmons Podcast. “Your head goes there. Kawhi hasn’t won a playoff series in five years. Kawhi, with the Clippers, won two playoff series in seven years and missed more games than just about anybody other than Embiid the last six.”

If the Raptors can realize their Kawhi Leonard vision, the cost won’t matter much

Kawhi Leonard averaged 27.9 points on 50.5% shooting from the field and 38.7% from deep, 6.4 rebounds, 3.6 assists, and 1.9 steals over 65 games last season. If he can bring that kind of production to the Raptors, it would give them the offensive lift they need and strengthen an already good defense. 

When he’s healthy, he and Barnes will make for one of the scarier two-way duos in the NBA, and the force of those two together promises a deep playoff run and potential title contention. 

There are justified concerns about Leonard’s injury risk and spotty availability, but the potential is too high to ignore. And if Leonard is healthy enough to contribute to a strong regular season and lead the team on a deep playoff run, no one in Toronto will care if it cost them more to get him than what the 76ers gave up for Jaylen Brown. 

However, that will look very different if Leonard is never healthy enough to help the Raptors contend with the top teams in the league, and they waste precious years of Scottie Barnes’s mid-twenties. 

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