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Kawhi Leonard’s Free Agency Future: A Study In Known Unknowns

Nikola Cuvalo

Courtesy of the Toronto Raptors Twitter

Kawhi Leonard, the man with catcher’s mitts for hands, a laugh generated by a 90’s sound sequencer and a stone-faced expression akin to an Easter Island head, is a top-5 player in the NBA when healthy. After years of toiling in successful-but-small-market San Antonio, one might think that he would delight in playing for the Raptors in Toronto, the league’s 4th largest media market -- behind New York/Brooklyn, Los Angeles, and Chicago. It’s impossible to tell.

Kawhi tends to let his game do the talking, and says very little about anything unrelated to on-court activities; even when discussing X’s and O’s, his responses are typically short, bordering on blunt. There is an efficiency to his speech that seems almost unnerving: as if you’re holding a conversation with Siri or Alexa -- just in a chiseled, 6’7” frame. In an age where professional athletes and sports personalities are more outspoken than ever, Kawhi is the rough equivalent of a silence-sworn monk.

Thus, gauging Kawhi’s free-agency leanings tends be an exercise in frustration, often providing more uncertainty than clarity. The most optimal route to take in terms of forecasting his free-agency decision would be to stick to what we know thus far. Here is what we have to consider:

Where is he from?

NBA players often consider their hometown teams rather closely when making free-agency decisions -- think LeBron James returning to the Cleveland Cavaliers in the summer of 2014. Kawhi Leonard was born in Los Angeles, California, and played two seasons of college basketball for the San Diego State Aztecs.

Who’s in the running for his services?

It is no secret, therefore, that the two teams aside from the Raptors who will be seriously vying for his services this summer are the Los Angeles Lakers and the Los Angeles Clippers. The Lakers are an attractive destination, as the arrival of LeBron James has propelled the NBA’s most historic franchise into playoff contention once again. They will be able to clear a max contract slot for Kawhi on their roster without losing any members of their young, talented core of Lonzo Ball, Kyle Kuzma, Josh Hart, and Brandon Ingram.

The Clippers, however, are attractive in their own right: they can offer Kawhi all the benefits of Los Angeles, and the starring role on their roster. It’s unclear as to whether he wants to be a supporting star or assume a leadership role, but the Clippers can also pave their way to two max-contract spots, possibly aiming to sell Kawhi on the idea of choosing his own running-mate in their quest to raise the Clippers – long known as L.A.’s “other” franchise – to the kind of relevance only attainable via winning a championship.

What about the Raptors?

After 20 games of regular season basketball, the Raptors appear to be a bona-fide title contender, boasting an NBA-leading 16-4 record. Kawhi has fit extremely well into their system, is averaging an absolutely dominating 24ppg/11rpg/3apg, and seems to be thoroughly enjoying his time in Toronto - an eminently underrated city among NBA players. The team appears to be building chemistry, and has handled his prior quadriceps injury carefully -- which was a major reason for his forced departure from the Spurs. Expectations this season are as high as can be: the Raptors are determined to participate in the NBA Finals for the first time in franchise history. Those are the sorts of expectations stars are drawn to, moreover, finishing the year with anything less can reasonably be considered a death knell to their chances of retaining Kawhi.

So what’s the verdict?

With the Raptors playing as well as they have been, it is difficult to imagine Kawhi leaving for “basketball reasons” - the ability to win more, or in some way achieve greater on-court success. Their case, ultimately, hinges on their postseason results and their continued fostering of a system that allows Kawhi to play at his absolute highest level. The Lakers and Clippers have both had strong starts to the season -- if not quite as successful in the standings -- but have the distinct advantage of being able bring Kawhi back home. The Lakers may be able to sell him on being the missing piece to their championship puzzle, while the Clippers may entice him with the notion of being “the guy” in his hometown, and helping a team that has long toiled in mediocrity to navigate the uncharted waters of long-term success.

All told, I’m willing to say that the totally-mathematically-verifiable odds right now are 50:50; that is to say, there is – as of this moment - a 50% chance he stays in Toronto for the next 5 years, and a 50% chance he bolts home to one of the two L.A. franchises. It’s as clear as could be.

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