The Toronto Raptors have officially added Kawhi Leonard's best friend, Jeremy Castleberry, to head coach Darko Rajakovic's coaching staff. This move coincides with Leonard's highly anticipated return to Toronto via trade from the Los Angeles Clippers for the 2026-2027 NBA season. The team is building around Leonard and a young core led by Scottie Barnes, who finished sixth last season before a first-round playoff exit.
Jeremy Castleberry's hiring is a direct effort to create a comfortable and supportive environment for Kawhi Leonard. Castleberry and Leonard have been close friends since they were 14 years old. Their basketball journey together includes playing on the same AAU team, at Martin Luther King High School, and later at San Diego State University.
Castleberry has been a constant presence in Leonard's professional career. He first joined the San Antonio Spurs staff as a video coordinator under Gregg Popovich. He then followed Leonard to Toronto for the 2018-19 championship season. After that, he spent seven seasons as an assistant coach with the LA Clippers. His return to the Raptors ensures a trusted confidant is on the bench for Leonard.
Kawhi Leonard made it clear his return is not primarily about chasing another NBA championship. In a team video, he explained his decision was deeply personal. "I'm not really championship-chasing, trying to find the best team I could win. I didn't want to put on a thousand jerseys," Leonard said. "My son was born here. He's been asking me forever when he's going to come back."
Leonard emphasized he is returning to help, not to take over. "I'm not here to take over anything. I want to help your vision, help Scottie; I just want to win," he stated. He acknowledged Scottie Barnes's growth, saying the young star "is going to be a problem this coming year." Leonard's focus is on integrating with the existing team structure.
Head coach Darko Rajakovic's finalized staff features a blend of experience and continuity. The lead assistant coaches are Pat Delany, Jama Mahlalela, and former Houston Rockets head coach Stephen Silas. Matt Vest has been promoted to assistant coach.
They are supported by returning assistants Ivo Simovic, Vin Bhavnani, Eric Khoury, Jim Sann, and Mery Andrade. Jeremy Castleberry rejoins this group. The video coordination and player development team is led by Ike Azotam and Kareem Elliott. New additions Stephane Ingo, Isiah Price, and Aidan Wilson join them.
Even at 35 years old, Kawhi Leonard remains an elite performer. Last season with the Clippers, he averaged 27.9 points, 6.4 rebounds, 3.6 assists, and 1.9 steals per game. He shot 50.5% from the field. Those numbers show no significant decline in his two-way impact.
Leonard believes the Raptors have a strong foundation. "I think we got a great chance," he said. "This group played great last year." He plans to study film over the summer to see how he can best fit in. Fans can track the team's progress on our standings page throughout the season.
His legendary 2019 championship run cemented his status in Toronto. Now, his role is to elevate a promising roster. The reunion with Castleberry provides a layer of off-court stability as Leonard shoulders a major load for a team looking to make a deeper playoff run.
