Toronto Raptors bring back 'Kawhi whisperer' to coaching staff

With the 2026-27 NBA season less than a month away, Toronto Raptors head coach Darko Rajakovic has finalized the coaching staff that will be on the bench with him this season.

Raptors fans will be happy to hear that there's one familiar face back with the team.

Now that Kawhi Leonard is a Raptor once again, it's only right that the "Kawhi whisperer" is back.

The Raptors announced Thursday that they have rehired Jeremy Castleberry as an assistant coach.

Raptors 2026-27 coaching staff

HC: Darko Rajakovic
Lead assistants: Pat Delany, Jama Mahlalela, Stephen Silas
Second row assts: Ivo Simovic, Vin Bhavnani, Eric Khouri, Jim Sann, Mery Andrade, Jeremy Castleberry (!), Matt Vest

— Josh Lewenberg (@JLew1050) September 17, 2026

Castleberry and Leonard have been lifelong friends, and he's been there for nearly every step of the superstar's professional career, aside from his first two seasons in the NBA with the San Antonio Spurs.

The two went to high school together in Riverside, Calif., before both attending San Diego State University and playing for the school's basketball team.

Castleberry was Kawhi's teammate during his final season at San Diego State before declaring for the 2011 NBA Draft.

The 35-year-old from Upper Marlboro, Md., spent the last six seasons as an assistant coach with the Clippers and previously served as an assistant with the Raptors when they won the NBA championship in 2019.

So, he has a pretty great track record in Toronto, just like Kawhi.

The Toronto Raptors acquired Kawhi Leonard in a June 30 trade with the Los Angeles Clippers in exchange for Brandon Ingram, Gradey Dick and several draft picks. (Dan Hamilton/Imagn Images)

The connection between the two must be special, considering Leonard has averaged more than 20 points and six rebounds per game in nine of the 13 seasons Castleberry has been behind the bench.

Leonard has also won two championships and made seven All-Star teams during that span.

Castleberry wasn't the only new hire brought onto Rajakovic's staff for the upcoming season.

Former Houston Rockets head coach Stephen Silas was brought on as an assistant coach, joining Pat Delany and Jama Mahlalela on the Raptors staff.

Silas held the Rockets' head coaching role for three seasons before being dismissed after compiling a 59-177 record.

He holds the worst winning percentage in NBA history among coaches with at least 200 games.

The Raptors had two vacancies to fill on their bench, with neither Mike Batiste nor James Wade returning for the 2026-27 season.