Given the widespread rumors that Kawhi Leonard is planning to leave the Toronto Raptors in the summer of 2019 and sign with his hometown Los Angeles Lakers or Clippers, the team appears to be doing what it could to ensure he re-signs the team when his contract comes up next year. This includes signing one of the former Spurs forward’s longtime friends and adding him to the Raptors coaching staff.
Reporting for ESPN on Tuesday, Ian Begley cited league sources, who told the network that the Raptors hired Jeremy Castleberry and gave him an unspecified position on their coaching staff. As further noted by ESPN, the friendship between Castleberry and Leonard goes back about a decade or so, as the two were high school basketball teammates who had also played in the same team at San Diego State University, where Castleberry played two seasons as a walk-on guard.
As further suggested by ESPN, there might be a specific reason why Jeremy Castleberry and Kawhi Leonard are reuniting on the Toronto Raptors. As Leonard will become a free agent in the summer of 2019, Raptors president Masai Ujiri “took [a] significant risk” when he agreed to trade DeMar DeRozan and Jakob Poeltl to the San Antonio Spurs in exchange for Leonard and Danny Green, and did so with the expectation that he would be able to re-sign Leonard once his contract comes up.
— Bleacher Report NBA (@BR_NBA) August 21, 2018
While Leonard has often been quoted as saying that he’d want to sign with the Lakers or Clippers once he hits free agency in the summer of 2019, ESPN posited that the Raptors’ decision to hire Castleberry “certainly won’t hurt” the team’s odds of re-signing the two-time former Defensive Player of the Year. If Leonard chooses to stay in Toronto, the Raptors would be able to re-sign him for five years and $190 million, but if he chooses to play elsewhere, he could end up taking a pay cut, as he would only be eligible for a four-year, $141 million contract with a team that has enough salary cap space to afford him.
Although the Raptors are seemingly doing what they could to keep Kawhi Leonard in Toronto for the next several years, recent reports have suggested that one other NBA team is planning ahead in hopes of luring the 27-year-old forward once he hits free agency.
Last week, former San Antonio Spurs defensive stalwart and Los Angeles Clippers analyst Bruce Bowen confirmed that the Clippers had indeed fired him for making critical comments about Leonard’s past trade demands while still playing for the Spurs. According to Uproxx, this move was reportedly necessary because the Clippers felt the comments might affect their chances of signing Leonard as a free agent in the 2019 offseason.