- The Toronto Raptors have already begun their year-long recruitment effort to convince Leonard to re-sign after the 2018-19 season.
- The team is reportedly set to add Jeremy Castleberry, a close friend of Leonard, to the coaching staff.
- Beyond whatever success the Raptors have this season, it’s likely that the Raptors’ decision to trade for Leonard will be judged mostly on whether the team is successful in keeping him beyond the one season.
The Toronto Raptors landed one of the biggest prizes of the NBA offseason, bringing in San Antonio Spurs superstar Kawhi Leonard in exchange for their own All-Star, DeMar DeRozan.
When healthy, Leonard is one of the top players in the NBA, but the Raptors’ move came with some inherent risk, as Leonard is only under contract for one more season, and has been clear about his desire to play in Los Angeles.
Knowing that they will be competing with the entire free agency market in their effort to keep Kawhi through the next offseason, Toronto’s 2018-19 campaign will likely be a year-long recruitment effort to keep Leonard happy, and the process has already begun.
On Tuesday, ESPN’s Ian Begley reported that the Raptors are set to sign Jeremy Castleberry, a close friend of Leonard, to the team’s coaching staff. Castleberry worked with Leonard as a staffer with the Spurs and played with him through high school and college at San Diego State.
While Castleberry’s tenure with the Spurs speaks to his bona fides – Gregg Popovich isn’t in the business of hiring staffers to please his players – the move does signal how broad an effort the Raptors will likely make to keep their new superstar.
Having a friend on the coaching staff isn’t the only advantage Toronto will have heading into the 2019 offseason. As the team currently holding Leonard’s rights, the Raptors will have the option to offer Leonard a five-year, $US190 million contract when he becomes a free agent next year.
For other teams pursuing him, the biggest offer they can make is a four-year, $US141 million deal. If Leonard would prefer to lock in his paycheck for an extra year – no small thing for a player that missed almost the entire 2017-18 season – Toronto will be his best bet.
The Raptors were already set to be a force in the East through the upcoming season. Toronto finished last year with the best record in the conference, only to be swept out of the playoffs by LeBron James and the Cleveland Cavaliers for the second straight year. With James now playing in the West, the Raptors had a path to the Eastern Finals if they brought the same team back.
In signing Leonard, the Raptors took a risk, and the success or failure of the move will likely be judged more by whether or not Toronto can successfully convince him to stay than any run the Raptors go on this year short of winning a title.
The Raptors have ten months until Kawhi Leonard decides whether Toronto is the place he wants to spend the peak years of his career, and the team is going to do everything in its power to keep him happy.
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