Seven years after Kawhi Leonard delivered the first championship in franchise history, Toronto has brought him back, betting once again that the risk is worth the reward.The Raptors surrendered significant assets to make the move, reportedly sending Brandon Ingram, Gradey Dick, two first-round picks, a first-round swap and two second-round selections to the Clippers.The cost is substantial, but Toronto has already seen this story play out once before.In 2018, the Raptors traded DeMar DeRozan, Jakob Poeltl and a first-round pick to acquire Leonard despite concerns surrounding his health. The move resulted in an NBA championship and one of the greatest playoff runs in league history.Leonard averaged 31 points, nine rebounds and four assists during the 2019 postseason while shooting 49/38/88 splits. He eliminated Philadelphia with his iconic Game Seven buzzer-beater before leading Toronto past Milwaukee and Golden State to capture his second Finals MVP award.The biggest concern this time is not Leonards talent. It is his health.Leonard has missed approximately 40 percent of regular-season games and thirty percent of playoff games during his seven seasons with the Clippers. He missed the entire 2021-22 season after suffering a torn ACL and has continued to deal with knee inflammation in recent years.Despite those concerns, the 34-year-old enjoyed one of the strongest seasons of his career in 2025-26. Leonard averaged 28 points, six rebounds and four assists while shooting 51/39/89 splits across 65 games. He also received MVP and All-NBA First Team consideration.There is also ongoing scrutiny surrounding Leonard and the Clippers. A Pulitzer Prize-winning investigation by Pablo Torre alleged that Leonard received additional compensation through a no-show job arrangement that earned him another $50 million.Related Article: Kawhi Leonard Trade Buzz Grows: The Juiciest RumorsMeanwhile, NBA insider Chris Haynes reported that Leonard is already discussing a two-year extension with Toronto.The Raptors enter next season with Scottie Barnes, RJ Barrett, Immanuel Quickley and Collin Murray-Boyles surrounding Leonard in what appears to be a wide-open Eastern Conference.READ MORE: 3x Lakers Champion Says Lakers Must Move on From LeBron James
