The Toronto Raptors have landed a new key coaching addition to further satisfy Kawhi Leonard in their offseason reunion.
On Thursday, Toronto officially unveiled its coaching staff ahead of the 2026-27 season, announcing the addition of Jeremy Castleberry to join Darko Rajakovic.
Castleberry joins Stephen Silas as one of the new faces within the Raptors for the upcoming season.
Jeremy Castleberry joins Kawhi Leonard again in Raptors return
Jeremy Castleberry, Kawhi Leonard’s longtime best friend, has followed the NBA superstar once again, this time in his return to Toronto.
Castleberry and Leonard have been close since they were 14 years old. They first met while playing for the same AAU team and later became teammates at Martin Luther King High School and San Diego State University.
Castleberry has been involved with Leonard throughout his professional career. After the San Antonio Spurs landed Leonard in 2011, Castleberry joined the organization and eventually worked as a video room staffer under Gregg Popovich.
When Leonard was traded to Toronto, Castleberry followed him to the Raptors. He then made the move to the LA Clippers when Leonard left Toronto in 2019 after their NBA championship run.
Castleberry’s move to Toronto marks another chapter in his long partnership with Leonard. As such, his hiring should be pivotal to keep the superstar comfortable and happy in his second stint as a Raptor.
Stephen Silas joins Darko Rajakovic Raptors coaching staff
Along with Jeremy Castleberry, Stephen Silas has also joined the Toronto Raptors as an assistant following the departures of James Wade and Mike Batiste.
Silas previously served as an assistant coach of Monty Williams for the Detroit Pistons during the 2023-24 season. Prior to that, he already had extensive experience as an assistant with the Charlotte Hornets (2000-2002), New Orleans Hornets (2002-2003), Cleveland Cavaliers (2003-2005), Golden State Warriors (2006-2010), Charlotte Bobcats (2010-2018), and the Dallas Mavericks (2018-2020).
He was the Houston Rockets' head coach, serving from 2020 until his dismissal in 2023.
Silas is the son of late three-time NBA champion and longtime head coach Paul Silas.