Michelle Beadle weighs in on how Toronto will fare in the race to attract Kawhi Leonard in free agency after hiring his friend to a coaching staff position. (0:35)

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.

The Spurs traded Leonard and Danny Green to Toronto for DeMar DeRozan, Jakob Poeltl and a protected 2019 first-round pick last month.

Leonard can test free agency in the summer of 2019, so Raptors president of basketball operations Masai Ujiri took significant risk with the transaction. Ujiri made the deal with a determination that he can convince Leonard to re-sign with the Raptors next summer in free agency, sources told ESPN's Adrian Wojnarowski.

Hiring Castleberry certainly won't hurt Toronto's chances of keeping Leonard.

The Raptors would be able to offer Leonard a five-year, $190 million contract next summer. If Leonard leaves the Raptors, he could sign a four-year, $141 million deal with a team with the available salary-cap space.

So far, Leonard's preference is to sign in Los Angeles with either the Lakers or Clippers next season, sources told Wojnarowski.