Toronto Raptors Face Kawhi Leonard Decision As Investigation Nears End

September has officially arrived, which means training camp and media day are almost here for the 30 NBA franchises. The Toronto Raptors may be dreading the start of the season, as they would likely prefer to have more time to allow for the Kawhi Leonard investigation to end. Once it does, general manager Bobby Webster will finally be able to assess the potential penalties levied against the seven-time All-Star, then decide whether or not to complete the trade for him. 

In all likelihood, the deal will be official; that is, as long as Leonard’s contract isn’t terminated. In that scenario, it wouldn’t make sense for the Raptors to give up the extensive draft capital along with Brandon Ingram and Gradey Dick for a player who technically will be an unrestricted free agent. Either way, it’s widely anticipated that the former San Diego State Aztec will become a Raptor for the second time in his career one way or another. 

Most fans are focusing on the destiny for Toronto next season, and rightfully so, but it’s important to assess the future as well. One of the main reasons for Leonard’s desire to be traded to the Raptors again is that he knew they would sign him to an extension right away. The situation is not a matter of whether Webster will give the two-time Finals MVP an extension, but rather of how much money and for how many years. 

As the investigation continues to drag on, it is diverting attention from Leonard’s future in the NBA beyond next season. At 35 years old and entering his 16th season, he just had one of the best years of his career. The two-time DPOY played in the fifth-most regular-season games in a year for his career and simultaneously achieved his career-high in points per game (27.9) for a season. 

On the flip side, the former No. 15 pick in the 2011 NBA draft played in 60 games only twice in his seven years with the Los Angeles Clippers. Generally known as a soft-spoken guy, Leonard hasn’t made his retirement plans public, so it’s unknown whether he plans to only play a few more years or follow in the footsteps of Raptors legend Kyle Lowry, who retired after 20 seasons. 

Like many other superstars, the timing of his retirement could depend on how his later years continue to pan out. If he plays some of his best basketball moving forward as he did last season, there may be no reason for him to hang up the shoes soon. That’s especially true if Webster gives Leonard a max extension, but that’s where the risk comes in. Unfortunately, the NBA 75th Anniversary Team selection is one of the most unreliable superstars in the league because of his consistent injury issues. With the team already struggling to find space in the salary cap because of the detrimental Immanuel Quickley and Jakob Poeltl contracts, is it worth going into the luxury tax or even one of the apron tiers to pursue a championship with an injury-prone star?

NBA on Prime’s Chris Haynes reported immediately after the trade announcement that Leonard and the Raptors would meet to discuss a two-year extension. This timing could be ideal for Toronto, considering that would be the same period in which Quickley’s and Collin Murray-Boyles’ contracts would end. Scottie Barnes and Poeltl would have just one year left on their respective deals, giving the franchise two years to assess the contracts of most of the key players after a three-year championship window. Anything close to a max deal would severely limit the depth of the bench, as well as the opportunity to give RJ Barrett a new contract similar to what he’s earning now ($29.6 million). 

It’s not impossible that Leonard continues to play after three more years, but if he were to finish his career on this extension, it may not make sense to make him one of the highest-paid players in the NBA if he does not maintain his value through 2029. Webster hasn’t been tasked with many major decisions so far in his tenure as the head of basketball operations, but the next few years could very quickly determine whether or not he’s able to keep his role for the foreseeable future.