​Kawhi Leonard’s second stint with the Toronto Raptors remains on hold. At one point, the probability of Leonard returning to Toronto was as high as 98.1% before the deal halted progress. By Saturday evening, July 11, at 10:25 p.m. Eastern time, Kalshi had pegged Toronto as an 82% favorite to land Leonard as his next team. Staying with the Los Angeles Clippers or retiring stood at 17%, with more than $667,000 in trades recorded.
Polymarket showed even greater enthusiasm for a reunion, pricing Toronto at an 87% likelihood, while the Clippers dropped to 11% and the San Antonio Spurs to 3%, on more than $153,000 in volume. Those opinions persisted despite an NBA investigation that has delayed a trade the teams had already agreed to complete.
The level of confidence in a final trade is guided not only by nostalgia from 2019 but also by the numbers involved. ESPN reported on June 30 that the Clippers had agreed to send Leonard to Toronto in exchange for Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a 2027 first-round pick swap, and two second-round picks. In addition, Leonard’s stated preference gave Toronto a compelling reason to push the deal across the finish line. As the Clippers explored multiple options, Leonard stated that he would only sign an extension with the Raptors, a detail highlighted in the ESPN report. That stance influenced Minnesota and Detroit, who did not pursue the pursuit further without a long-term commitment from the star.
Leonard has one season remaining on his contract with $50.3 million owed to him. If the trade were completed, he would become eligible for a two-year extension worth up to $123.7 million. ESPN also reported that Leonard had hired Harrison Gaines as his new agent to handle negotiations with Toronto.
From Toronto’s perspective, the financial risk of acquiring a 35-year-old player with a substantial injury history is significant, yet the appeal is evident. Leonard averaged a career-high 27.9 points per game with 6.4 rebounds across 65 games last season, finishing seventh in MVP voting. Returning to the organization that delivered its lone championship and where he earned his second NBA Finals MVP in 2019 would place him in a familiar and high-impact environment. It’s not common to see a postseason scorer and perimeter defender of Leonard’s caliber readily available on the market, which adds to Toronto’s long-term incentives to finalize the deal.
The agreement never reached official status because Toronto chose to pause the trade given the uncertainty surrounding Leonard’s contract amid ongoing league scrutiny. The Raptors paused the proceedings after the NBA informed them they would bear the risk of any outcome from the investigation that could affect Leonard.
The probe centers on allegations that a $28 million endorsement arrangement between Leonard and Aspiration, the company now bankrupt, may have been used to circumvent salary-cap rules. Aspiration had close financial ties to Clippers owner Steve Ballmer. Both the Clippers and Leonard have denied any wrongdoing. Toronto’s public stance has suggested that their interest in bringing Leonard back remains strong, even as they await a swift resolution to the matter surrounding the investigation. The Raptors stated publicly that they remained eager to bring Kawhi back to Toronto and looked forward to a quick resolution for their players and organization, underscoring the ongoing optimism about the potential reunion.