Anything to make him happy.
The Toronto Raptors made a rather interesting move on Monday, hiring Jeremy Castleberry away from the San Antonio Spurs to be their player development coach, according to multiple reports. Castleberry was the Spurs’ video coordinator.
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
This move is making waves because Castleberry and Kawhi Leonard are childhood friends, playing on the same high school and college basketball teams. Castleberry is said to be Leonard’s very frequent workout partner, which includes all hours of the day and the offseason.
It is apparent that Castleberry and Leonard are close, but they may be closer than many think. ESPN’s Ramona Shelburne calls Castleberry one of Leonard’s ‘closest confidantes’ and is his best friend, according to some.
— Lisa Lane (@LisaLane_Sports) February 16, 2014
The decision to bring in Castleberry seems pretty simple. With one year left on his contract and his stated desire to play in Los Angeles, Raptors president Masai Ujiri has one season to convince Leonard to re-sign in Toronto.
Having a familiar face that Leonard has known for a long time will be important for the All-Star. Leonard is known not to talk that much and keep to himself, but by having his best friend on the coaching staff it will no doubt help Leonard adjust to being in a new locker room and keep him comfortable in Toronto.
Obviously, this is such a small move for Toronto’s front office to make, but hiring Castleberry won’t hurt the Raptors’ chances of keeping Leonard, it will only improve them.
Leonard will be under contract for just this upcoming season and the most Toronto will be able to offer him is a five-year, $190 million contract next summer. Should Leonard leave the Raptors, he could sign up to a four-year, $141 million deal.
If Leonard does, in fact, leave Toronto after this season, at least Bobby Webster and Ujiri have tried to go for it and are trying to make Leonard the most comfortable he can be in a new country and playing for a new team for the first time in his career.