Insider Offers Potential Raptors' Kawhi Leonard Trade Timeline

Team USA Stripes forward Kawhi Leonard of the LA Clippers. IMAGN IMAGES via Reuters Connect

Insider Offers Potential Raptors' Kawhi Leonard Trade Timeline

Originally posted on Toronto Raptors on SI
By Jeremy Brener | Last updated Aug 18, 2026 7:00 AM ET

The Toronto Raptors are hopefully getting closer to the end of the Kawhi Leonard investigation, which will allow them to push forward a trade that would bring the two-time Finals MVP to the roster.

In the proposed deal, the Raptors would send Brandon Ingram, Gradey Dick and multiple first-round picks to the Los Angeles Clippers for Leonard once the league concludes its investigation into alleged salary cap circumvention.

The Raptors' roster and rotation looks entirely different if the trade goes through. They have every intention of completing the deal, so they have to get it done before training camp begins next month.

ESPN insider Baxter Holmes is reporting that the NBA has not found any evidence to suggest that the Clippers circumvented the salary cap, but the investigation is still not complete. Holmes did appear on ESPN programming to discuss the trade and when it could possibly be finalized.

Baxter Holmes on the pending Raptors-Clippers trade following the ESPN article that dropped today that the NBA found no evidence of the Clippers/Ballmer funnelling money to Leonard via sponsors:

“It doesn’t really add any clarity to what as to when there could be a resolution… pic.twitter.com/I8v0ASsdW6
— Omer Osman (@OmerOsman200) August 17, 2026

Kawhi Leonard Investigation, Trade Should Be Close to Completion

“In mid-September, there’s going to be an NBA Board of Governors meeting, and I think that will serve as kind of an inflection point as to, ‘we might have some clarity by then.' If not by then, potentially by the end of the month, at the very least, when media day and training camps are set to begin for the coming season," Holmes said.

Leonard and the Raptors have been operating as though this trade is only a matter of when rather than if. The major concern, and the reason why the deal hasn't been completed yet, is that Leonard would have his contract voided. That would dismantle the entire trade and return players back to their original locations.

The report suggests that Leonard is not going to face any punishment, which is a good sign for the Raptors, but they still need to wait until the league is able to push the trade through.

Leonard has been spotted a few times in Toronto in recent weeks, which leads many to believe that he is insistent on coming to the Raptors. The whole reason the trade took place to begin with is because Leonard said he would only re-sign with Toronto once he became a free agent in the 2027 offseason.

Leonard is definitely going to get his chance to return to the Raptors, where he helped win a championship in 2019. The investigation is still preventing this blockbuster trade from happening, but it seems like the wait is not going to last much longer.