The Raptors Hired Kawhi Leonard’s Bestie Before the NBA Season Starts Jason Cordner August 21, 2018 Digital Entertainment, Source Sports | News, Highlights and Interviews The Toronto Raptors are doing everything they can to get on Kawhi Leonard’s good side. The Athletic’s Shams Charania reported on Monday that the Raptors have hired Jeremy Castleberry as a player development coach. Castleberry and Leonard have a very long history and friendship. Sources: The Raptors are hiring Spurs assistant video coordinator Jeremy Castleberry as a player development coach. Castleberry earned degree at SDSU, worked his way up in Spurs system from video room. — Shams Charania (@ShamsCharania) August 20, 2018 Castleberry played with Leonard in high school and college. He was previously an assistant video coordinator for the Spurs, so becoming a player development coach with Toronto is a step up. The Raptors acquired Leonard in a trade with San Antonio over the summer. They took a big risk by dealing franchise cornerstone DeMar DeRozan and a protected first-round pick to the Spurs despite knowing that Leonard could leave as a free agent next year. Leonard has made his intentions known he prefers to play in his home city of Los Angeles. Leonard will be one of the top 2 free agents being sought after in the summer of 2019. The Raptors are wise to do what they can now to keep him around past June 2019.