When the Toronto Raptors swung the blockbuster trade for Kawhi Leonard earlier this summer, it represented a huge risk for the franchise. Not only did they give up an All-Star and fan favorite in DeMar DeRozan along with a first-round pick, but Leonard is a free agent next summer and might end up leaving. 

If the Raptors don't meet expectations this season and Leonard leaves, they could wind up in rebuilding mode very quickly. Which is why they'll do everything in their power to convince Leonard to stay in Toronto long term. We've seen that this strategy can work, as just this summer the Thunder were able to convince Paul George to spurn Los Angeles to stay in Oklahoma City. Masai Ujiri and the Raptors will hope they can do the same. And they've already started their mission. 

According to a report from Ian Begley, the Raptors have added Leonard's longtime friend and former San Antonio Spurs staffer, Jeremy Castleberry, to their coaching staff. Via ESPN:

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.

Adding friends or confidants to the staff in order to appease a star player is nothing new in the NBA, as CBS Sports' Raja Bell knows firsthand. He discussed this Raptors situation on a recent episode of the Off the Bench on CBS Sports HQ, as well as telling a story about a similar scenario when he was playing with the Cleveland Cavaliers. As Bell explained, it makes sense from the team's perspective, but it can also backfire. 

"Yeah, that could create a whole lot of issues when you're hiring guys like that," Bell said. "But it depends on what positions you have them in."

It's not hard to see why this could potentially be a problem as the Raptors catering to Leonard could upset other players or potentially cause a rift in the locker room. But that's a risk the Raptors are just going to have to take as convincing Leonard to re-sign next summer will make or break the future of their franchise. 

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