The Toronto Raptors are out of league office purgatory and are officially announcing their brand-new roster and staff. After the Kawhi Leonard trade finally went through, the team officially finalized their coaching staff for the upcoming 2026–27 season. Among the new coaching staff, one name marked a notable roster addition that carries significant personal meaning for their newly re-acquired superstar.
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As part of a sweeping staff announcement by head coach Darko Rajaković, Toronto confirmed the return of assistant coach Jeremy Castleberry. While he was on the Raptors’ 2019 championship staff, he’s better known in league circles as the “Kawhi whisperer” and the 2x Finals MVP’s closest confidant.
The official release detailing Rajaković’s bench composition confirmed Castleberry’s return to the franchise following a multi-year absence:
“The Toronto Raptors announced Thursday that head coach Darko Rajaković has finalized his coaching staff for the 2026-27 season, with Stephen Silas joining Pat Delany and Jama Mahlalela as assistant coaches on the front bench. Matt Vest has been elevated to assistant coach, while Jeremy Castleberry returns to the Raptors staff along with Ivo Simović, Vin Bhavnani, Eric Khoury, Jim Sann and Mery Andrade.”
The organization further detailed Castleberry’s history with Toronto and across the league in his official profile:
“Castleberry returns for his second season in Toronto after joining the Championship-winning staff during the 2018-19 season. He spent the past five seasons (2019-2026) as an assistant coach with the Los Angeles Clippers and spent five seasons (2013-18) within San Antonio Spurs organization prior to joining the Raptors in 2018. Castleberry began his professional career with the Austin Spurs (then the Austin Toros) of the NBA G League, before being elevated to the Spurs staff where he worked as an assistant video coordinator. A native of Upper Marlboro, Maryland, Castleberry played two seasons at San Diego State (2011-13).”
While the announcement formally completes Rajaković’s staff alongside former Houston Rockets head coach Stephen Silas, the timing and context of Castleberry’s hire have immediately drawn headlines across the league.
Castleberry is almost always perceived as a personal hire wherever Kawhi Leonard goes. They’re best friends whose deep, two-decade friendship predates their NBA careers.
The pair first met on the AAU circuit at age 14 before becoming high school teammates at Martin Luther King High School in Riverside, California. They later suited up together at San Diego State University during the 2010–11 collegiate campaign.
Since Leonard entered the professional ranks, Castleberry has been embedded within his inner circle, securing staff roles alongside Leonard at every single stop of his NBA career, first with the San Antonio Spurs, then during Toronto’s historic 2019 title run, and most recently with the Los Angeles Clippers.
The move to bring Castleberry back to Canada comes just days after the NBA concluded its year-long investigation into the Los Angeles Clippers’ salary cap circumvention scandal.
The league levied unprecedented penalties against Los Angeles, that was not limited to docking the franchise five first-round draft picks, handing owner Steve Ballmer a $30 million fine and a one-year suspension, and imposing personal fines on Leonard ($700,000) while banning his former business manager/Uncle, Dennis Robertson, from conducting team-related business for five years.
Toronto originally agreed to acquire Leonard from Los Angeles in late June, but the Raptors paused the trade to await the league’s final ruling. After Ballmer accepted the punishment, the Clippers and Raptors could refocus on the stalled transaction.
Kawhi is committed to supporting the Raptors’ new young core, but the team is counting on his veteran presence to recreate the structure that helped deliver the 2019 Larry O’Brien Trophy.
By bringing Castleberry back to Rajakovic’s bench, the Raptors are giving Kawhi the same sense of comfort he’s relied on throughout his career. With Leonard back in Toronto for the 2026–27 season, making sure their franchise star feels supported both on and off the court remains a major priority.