The Toronto Raptors have reportedly hired someone named Jeremy Castleberry away from the Spurs to join their coaching staff. This is noteworthy because Castleberry played basketball with Kawhi Leonard in high school, and at San Diego State, and worked with Kawhi in San Antonio, and according to ESPN is “a close friend” of Leonard today.
This seems pretty transparently to be a recruiting tool, but it isn’t the worst idea in the world. The Raptors are on the clock. They dealt away the franchise’s all-time leading scorer and a promising young big man to acquire Leonard this summer, along with a protected future first-round draft pick, all despite knowing that Leonard is determined to play in Los Angeles. The move cost them the good will of the face of their franchise, and probably some good will from fans along the way. This needs to work! And if the organization is to have any chance in the universe of convincing Kawhi that Canada will be just as cool a home as [gulp] Los Angeles, they’ll need to start by fitting him into their basketball program as seamlessly as possible, a job that will be made much easier by the presence of some friendly faces in the building who’ve had success working with Leonard in the past.
It’s also the case that Kawhi might be, umm, a little difficult, and his relationship with the Spurs utterly crumbled over the course of last season, and understanding exactly how that happened, from as many angles as possible, could conceivably help the Raptors avoid any pratfalls in the developing of a sustainable relationship with their new superstar. Presumably Castleberry can help GM Masai Ujiri and new head coach Nick Nurse navigate what will inevitably be a pressure-packed and condensed period of courtship, without pissing Leonard off and chasing him all the way to Los Angeles.
Toronto’s retention pitch will rely on a few strengths: neither L.A. team is especially poised to challenge for supremacy in the brutal West; the Raptors have a stable organization and a deep roster and are immediate Finals contenders in the crappy East; and they can offer Leonard an extra year and something like $50 million more in free agency than other suitors next summer. Maybe having his boy on staff will sweeten what is already a pretty tasty offering, all things considered.
But it’s also the case that this is a move only teams facing recruitment or retention disadvantages ever really make. The Wizards hired Scott Brooks because they hoped to woo Kevin Durant in free agency, and knew they couldn’t do it on pure basketball terms, and that play mostly blew up in their dipshit faces. If hiring Castleberry is Toronto’s way of tilting the balance a touch more in their direction, it’s also inevitably an admission that things are starting off tilted wildly against them. It’s not quite as desperate as the Clippers dumping a broadcaster over some mild criticisms of Leonard, but it’s not far off.