Jeremy Castleberry played his high school ball in Riverside, California, on the same team as Kawhi Leonard. When Leonard went on to San Diego State for college, Castleberry went too and was a walk-on for that team.
When the Spurs drafted Leonard, it was not long before Castleberry was a video coordinator and on the staff in San Antonio. Now Leonard is a Raptor so… you know what’s coming. Adrian Wojnarowski of ESPN explained it well.
The Toronto Raptors are hiring San Antonio Spurs staffer Jeremy Castleberry — a close friend of Kawhi Leonard — to a position on their coaching staff, league sources told ESPN.
Castleberry has worked with Leonard as a Spurs staffer and played with Leonard in high school and at San Diego State, where he was a walk-on.
Is this alone going to keep Leonard a Raptor next summer when he’s a free agent? No. But this is how the game is played — make the star player you’re recruiting feel comfortable, wanted, a key part of everything. Bringing in a friend to a new city for him fits right into that plan.
The smart money is still on Leonard bolting next summer to go to Los Angeles, but if the Raptors are able to change his mind — ala Paul George — it will not be one big thing but a thousand little ones. And a lot of wins. But hiring Castleberry is a start.