Jeremy Castleberry Returns to Toronto Raptors With Kawhi Leonard After 'Punishment' Hits Los Angeles Clippers
The Raptors have reunited Kawhi Leonard with longtime confidant Jeremy Castleberry, who returns to Toronto’s coaching staff shortly after the NBA punished the Clippers in its salary-cap case.
Kawhi Leonard is back in Toronto, and one familiar face will be beside him again. The Raptors have brought Jeremy Castleberry back to their coaching staff just days after the NBA handed down major penalties to the Los Angeles Clippers over their salary-cap case involving Leonard.
Toronto confirmed Castleberry's return on September 17 as Darko Rajaković finalized his 2026-27 coaching staff. Castleberry was part of the Raptors' 2019 championship staff and later spent five seasons with the Clippers, making his return especially notable with Leonard now back in Toronto.
Raptors Add Jeremy Castleberry As Kawhi Leonard Returns
Castleberry is not a new name in Toronto. He first joined the Raptors during their 2018-19 title season and now returns after working with the Clippers from 2019 through 2026. The Raptors' official announcement said, “Jeremy Castleberry returns to the Raptors staff,” confirming his place on Rajaković's bench.
His connection with Leonard goes back much further than their NBA careers. The two have been close since their teenage years and later played together at San Diego State. Castleberry then worked around Leonard during his time with San Antonio, Toronto and Los Angeles, making their long professional relationship unusual in the NBA.
That history gives Castleberry's return extra attention, even though Toronto has not said he was brought back specifically for Leonard. The timing is striking because the Raptors have just completed their new-look staff while also bringing back the player who helped deliver the franchise's first championship in 2019.
Kawhi Leonard's Toronto Return Comes After Clippers Punishment
Leonard's return to Toronto comes shortly after the NBA completed its investigation into the Clippers. On September 2, the league said Los Angeles violated salary-cap rules and took action against the franchise, Steve Ballmer, Leonard and team executives following its investigation.
The Clippers were ordered to give up five first-round picks from 2029 through 2033 and pay a $30 million fine. Ballmer was suspended for one year, while Leonard was fined $700,000. His former business manager, Dennis Robertson, was also banned from NBA-related business for five years.
The timing now puts Castleberry and Leonard together in Toronto as the Raptors begin a new season. NBA.com confirmed that Toronto acquired Leonard from the Clippers for Brandon Ingram, Gradey Dick, future draft picks and a pick swap. Leonard returns to the team where he won the 2019 championship and Finals MVP.