Raptors, Ujiri playing chess with latest reported hiring

Raptors play-by-play voice Matt Devlin joins The Jeff Blair Show to discuss why the club hiring Kawhi Leonard’s close friend Jeremy Castleberry is great for more than the obvious reason.

The Toronto Raptors head into next season with an ulterior motive beyond winning — something the team appears poised to do plenty of in 2018-19.

And the Raptors’ latest reported hiring could help accomplish their secondary goal. At least that’s the hope.

The team is set to bring former San Antonio Spurs video coordinator Jeremy Castleberry on board to Nick Nurse’s coaching staff as a player development coach, as first reported by The Athletic’s Shams Charania.

Needless to say, that Castleberry is a close and longtime friend of recently acquired superstar Kawhi Leonard is not a coincidence.

Their friendship goes back to their AAU days where they played at the age of 14 and were teammates again at Martin Luther King Jr. high school in Riverside, Calif. Castleberry, who was described as “the consummate team player,” went on to attend San Diego State University with Leonard, and earned fan-favourite status after making the Aztecs’ varsity basketball team as a five-foot-10, 205-pound walk-on in 2009. When Leonard left the school after his sophomore season to join the NBA ranks, drafted 15th overall in 2011, Castleberry remained at school but regularly travelled to San Antonio whenever he could.

Upon his graduation in 2013, the Spurs hired Castleberry to join their staff.

Yes, Castleberry brings experience working in one of the most respected organizations in sports. But his hiring comes as the latest — and to date the most significant — move in Masai Ujiri and the Raptors’ plan to convince Leonard to remain in Toronto and re-sign with the team beyond next season, a chess maneuvere executed with several future steps in mind.

At the very least it will help to facilitate as smooth a transition as possible to Leonard’s new surroundings.

Those I’ve spoken to who were in the Spurs organization during Leonard’s last few seasons in San Antonio maintain that, while he may be quiet and reserved, Leonard is far more personable than his public persona suggests. And while there are naturally misconceptions about the private 27-year-old superstar, there’s no debating that having a close confidant along with him in Toronto could go a long way in making this upcoming season — the first in his career spent on any other team — as comfortable as possible.

The Raptors are hardly breaking precedent by bringing a close friend of a player onto their staff. In the NBA that is a fairly common practice, for obvious reasons. While Castleberry will surely help Leonard acclimate himself within the organization, he also happens to have excelled at his job during his time in San Antonio.

Again, the hiring provides Leonard with a close confidant along with the creature comforts of home and helps position the Raptors for what will be a season-long recruiting pitch. But that doesn’t guarantee a thing.

As reports of the hiring circulated Monday night, ESPN’s Adrian Wojnarowski stated that the NBA’s two Los Angeles franchises, the Lakers and Clippers, still remained as front-runners for Leonard’s services next summer, when he is expected to exercise his player option and opt out of his current deal to become an unrestricted free agent.

The Raptors will have an edge financially given that they can sign Leonard to a five-year, $190-million contract next summer, compared to the four-year, $141-million deal other clubs can offer. Leonard left even more money on the table by forcing his way out of San Antonio, which suggest money is not a chief motivator.

Regardless, the Castleberry hiring makes it clear that for Ujiri and Co. the game is now afoot.

Whether or not Leonard re-signs in Toronto, bringing a player of his calibre and pedigree to a Raptors team looking to break its current two-year streak of disappointing second-round playoff exits is a major coup for the club.

Leonard joins a 59-win team that is returning all of its players save for DeMar DeRozan and Jakob Poeltl, the two the Raptors had to send to San Antonio in order to land the former Finals MVP.

The rotation features Kyle Lowry, OG Anunoby, Jonas Valanciunas, Serge Ibaka, Danny Green, Fred VanVleet, Pascal Siakam, CJ Miles, Delon Wright, Norman Powell (who has appeared reinvigorated during scrimmages this summer), and newly-signed Greg Monroe.

Throw in guard Lorenzo Brown, who was named G League MVP last season after a stellar campaign for the Raptors 905, and a potential diamond in the rough in forward Chris Boucher, the Montrealer who spent last season with the Golden State Warriors and opened eyes playing for the Raps at the Las Vegas Summer League, and the Raptors roster could be as talented and deep than ever.

It’s why competing for the franchise’s first Finals appearance is — and should be — an attainable goal now that the team boasts arguably the best player in the conference. The lingering question that isn’t going away anytime soon remains: Can the Raptors keep Leonard beyond this season?

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