One of Kawhi Leonard’s closest confidants is rejoining the Toronto Raptors as the team looks to please their newly acquired superstar.
According to the team’s announcement, Leonard’s best friend Jeremy Castleberry rejoined the Raptors coaching staff, coinciding with Leonard’s return to Toronto for the upcoming 2026-2027 NBA season.
Castleberry was part of the finalized coaching lineup under head coach Darko Rajakovic, which also included former Houston Rockets head coach Stephen Silas.
Jama Mahlalela are Pat Delaney are joined by former Rockets head coach Stephen Silas as front of bench assistants.
Jeremy Castleberry And Kawhi Leonard’s Basketball History
Castleberry and Leonard share a deep personal history, having been close friends since they were 14 years old. Their journey includes playing together on the AAU circuit, as high school teammates at Martin Luther King High School, and later at San Diego State University.
Throughout Leonard’s professional career, Castleberry has consistently been a part of his inner circle and his teams’ coaching staff.
With the San Antonio Spurs, Castleberry joined the staff as a video room coordinator under Gregg Popovich.
He then followed Leonard to Toronto for the 2018-2019 season, capturing an NBA championship, the franchise’s first-ever.
Castleberry moved with Leonard to Los Angeles in 2019, spending seven seasons with the Clippers as an assistant coach.
Now, he returns to Toronto to continue being a close aide for Leonard, who is expected to carry a hefty load with the Raptors next season.
The front bench features lead assistant coaches Pat Delany, Jama Mahlalela, and Silas. Supporting them on the bench is Matt Vest, who has been elevated to assistant coach, alongside returning assistant coaches Ivo Simovic, Vin Bhavnani, Eric Khoury, Jim Sann, Mery Andrade, and the returning Castleberry.
The video coordination and player development group is led by Ike Azotam and Kareem Elliott, who are joined by new additions Stephane Ingo, Isiah Price, and Aidan Wilson.
Kawhi Leonard Is Not Chasing An NBA Championship In Toronto
Kawhi Leonard is not chasing an NBA championship in Toronto. Instead, he cited his son for why he joined the Raptors via trade from the Los Angeles Clippers.
“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,” said Leonard in a Raptors video. “My son was born here. He’s been asking me forever when he’s going to come back. Now he’s back, and he’s able to see it rather than me telling him the great stories.”
“I’m not here to take over anything. I want to help your vision, help Scottie; I just want to win. If it’s Scottie’s team, it’s his team. I just want to do whatever it takes to help you guys win.”
Leonard’s 2019 made him a legend in Toronto. Now, he returns to be the leader of an emerging young core led by Scottie Barnes after they finished sixth in the regular season last year and lost in the first round.
Even at 35 years old, Leonard showed no signs of slowing down after averaging 27.9 points, 6.4 rebounds, 3.6 assists, 1.9 steals, and 0.4 blocks per game on 50.5% shooting last season.
“I think we got a great chance,” Leonard said. “This group played great last year. I watched them a lot, and I’m going to watch more film in the summer to see how I can help. Scottie Barnes has shown his talents over the last two or three years… he’s going to be a problem this coming year.”
Toronto Raptors Add Kawhi Leonard Best Friend To Coaching Staff