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INGLEWOOD, CALIFORNIA - APRIL 02: Kawhi Leonard #2 of the Los Angeles Clippers on court against the San Antonio Spurs in the second half at Intuit Dome on April 02, 2026 in Inglewood, California. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Ronald Martinez/Getty Images)

The Toronto Raptors were able to win an NBA championship back in 2019 after trading for Kawhi Leonard. Leonard went to Toronto after being traded from the Spurs and only spent one year there. He led them to a title before signing with the Clippers.

Leonard has now emerged as the top trade target for multiple teams after Giannis Antetokounmpo was traded to Miami. However, the Clippers do not want to trade Leonard. They would prefer to keep him and see a way forward with him.

However, if the Raptors were to make a big offer for him, Leonard would be okay with it, according to insiders.

Kawhi Leonard Would Reportedly Sign a Contract Extension With the Raptors

According to NBA insider Jake Fischer, the only two teams that Leonard would consider signing an extension with if he were traded are the Raptors and the Spurs. Those are the two previous teams that he has played for. That means Toronto has a shot, if they offer the right package.

It’s unclear what the right package is for LA to part ways with Leonard. It’s also unclear what the status of the Aspiration investigation is. If that goes south, there could be some penalties for Leonard. The rumor was that the investigation was supposed to be finished before the Draft. That clearly was not the case.

For Toronto, they would likely offer everyone on the roster not named Scottie Barnes in a trade for Leonard, assuming he clears the investigation. Leonard also would like to remain with Los Angeles if it is up to him, which might be the biggest issue of all.

Still, it’s encouraging that Toronto would be a place he would consider playing long-term. The Raptors thought they were very close to keeping him before he left for Los Angeles, so they would feel great about getting him back. That would signal a strong win-now move.

Toronto Would Have Injury Concerns in a Kawhi Leonard Deal

If the Raptors were to trade for Leonard, they would have to be careful about assembling too many injury-prone players. Leonard has a well-documented history of injuries, even if he did have his healthiest season in years. Brandon Ingram has injury concerns, as well. Immanuel Quickley didn’t play at all in the playoffs.

Leonard had perhaps the best season of his career last season, dragging the Clippers to the play-in tournament. He finished the year averaging 27.9 points, 6.3 rebounds, and 3.6 assists per game on 50.5 percent shooting. He was a menace for the last two months of the year.

Toronto going all-in for an aging superstar would have an enormous amount of risk. The next contract Leonard signs will likely be his last, so picking the right team is just as important for him as it is for the team to choose to trade for him.