The Toronto Raptors have finished putting their bench together for the 2026-27 season, and one of the most recognizable names in the room is coming back.
Jeremy Castleberry has been rehired as an assistant coach, the team announced Thursday, giving Darko Rajakovic’s staff a familiar presence with a deep connection to Kawhi Leonard. With Leonard back in Toronto, the “Kawhi whisperer” is back too.
Castleberry and Leonard have been close since high school in Riverside, Calif., and their basketball paths have been linked for years. Both later attended San Diego State University, where Castleberry was Leonard’s teammate during Leonard’s final season before he entered the 2011 NBA Draft.
The 35-year-old from Upper Marlboro, Md., is no stranger to NBA benches. He spent the past six seasons as an assistant with the Clippers, and he also worked for the Raptors during their 2019 championship run. Toronto already knows what he can bring, and Leonard’s resume during that same stretch speaks for itself: in nine of the 13 seasons Castleberry has been on a bench, Leonard has averaged more than 20 points and six rebounds per game, while also collecting two championships and seven All-Star selections.
Castleberry isn’t the only addition for Rajakovic. Former Houston Rockets head coach Stephen Silas is also joining the Raptors as an assistant, alongside Pat Delany and Jama Mahlalela.
Silas spent three seasons leading Houston before being let go after a 59-177 record. That mark gives him the worst winning percentage in NBA history among coaches with at least 200 games.
Toronto had two openings to fill on the staff after neither Mike Batiste nor James Wade returned for the 2026-27 season. The full coaching group now includes Rajakovic, lead assistants Pat Delany, Jama Mahlalela and Stephen Silas, with Ivo Simovic, Vin Bhavnani, Eric Khouri, Jim Sann, Mery Andrade, Castleberry and Matt Vest listed in the second row of assistants.
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From Torontos perspective, the appeal is straightforward: extra rebounding, a steady voice in the locker room, and a player who has been around enough pressure to help set a tone. Love remains a free agent, and while no deal has been announced, the Raptors have at least left the door open to a possible fit if they decide veteran presence is worth one of the final spots on the roster. [Read more 🡒]