It’s damn near impossible to understand what Toronto Raptors star Kawhi Leonard wants. Leonard, along with his personal management, bungled his exit from the best organization in the NBA this past season. Leonard is now a member of the Raptors, who took a huge gamble by trading for him in order to move up in the Eastern Conference in the absence of LeBron James.
Seemingly, the result of the trade has not been a settling for either team. The Spurs don’t know exactly what they have with DeMar DeRozan, the return for exchanging the former Finals MVP to Ontario. For Toronto, it’s unclear whether Leonard even desires to stay in Canada, no matter the outcome of the season.
The question for Masai Ujiri and the rest of the Raptors organization is this: What can we do to entice Leonard to stay?
Toronto is a world-class city, and even if American sports fans don’t think of it often, the reality is that it is a metro area the size of Chicago. It has an advantage in that there’s plenty to do after an NBA game, between the hours of 10 p.m. and 2 a.m., when players are still awake thanks to their upside down sleeping schedule. (This, if you don’t know, is what separates the Houstons from the Portlands of the world.)
But Toronto also holds some drawbacks for many NBA players, including distance, “poor” weather, and high income taxes. Leonard, a California native, was rumored to have originally disliked Toronto as a destination because of the cold temperatures alone.
Ujiri & Co. also have a roadblock in front of them when it comes to winning. Yes, it is true that the Raptors — especially with Leonard on the roster — should be held as favorites to make the Eastern Conference Finals every season. They certainly will be in 2018-19. The Raptors are a perennial playoff team, and haven’t finished lower than sixth place since 2003.
The only problem with that? Leonard is already used to winning.
Leonard has never personally finished lower than third place, and even then that was only just last season when he didn’t see the floor but for nine games. And that was in the Western Conference, a decidedly better and more difficult place to play than out east.
Seemingly, there are only two factors that could play to Toronto’s advantage in keeping Leonard. The first is flipping his outlook on winning on its head.
Much like LeBron in Cleveland, the pitch for Leonard could be one that centers around the idea of having a team of his own that will always be vying for a spot in the Conference Finals. There is no end to the dominance of the West in sight, and that could be enticing for Leonard as he lives in a big city and cruises to 55-60 wins a season.
Ujiri could pitch Leonard as the new LeBron of the East, building a shining castle in Toronto. The new King in the North, for whom the road to playoff success is smooth and bereft of raiders, where veteran free agents come to try their shot at the NBA Finals. Ujiri could posit that each season would be a race for the others in the Eastern Conference to see who would meet the Raptors in the ECF, just as the Cavaliers had been penciled into that spot for a decade before.
The caveat here, of course, is that the Philadelphia 76ers and Boston Celtics have increased their own firepower over the past couple of seasons and, barring any injuries or natural disasters, they will remain in close competition with Toronto. Ujiri could pitch Leonard on being the new Cavaliers, but it wouldn’t make it true.
The other method of persuasion for Ujiri will be a sense of community and a primary focus on Leonard as a face of the franchise moving forward.
As much as Leonard was that in practice in San Antonio, it wasn’t a direct objective given that Gregg Popovich was always going to be the most important person in that building. While rumors of Leonard wanting to return to California have never wavered, neither have his apparent desire to be the solo star on a team (with supporting cast, of course).
As has been pointed out before, it’s possible that Ujiri has done damage to his reputation in the eyes of NBA players when it comes to keeping promises. Shipping DeRozan out of town could have an effect on Leonard, or it could not have. It might be exactly the opposite, signifying to Leonard that Ujiri is ready to do anything and everything to keep him happy, even if it’s drastic.
And yet, we still don’t know how Leonard feels about any of this or what his true motives are, and therein lies the problem.
Nobody outside of the Leonard camp has any concrete idea about what Kawhi wants to do at the end of this season when he can opt out of his current deal. It’s entirely possible that Kawhi doesn’t know. That pushes us back into the conversation about how poorly he has managed is exit from the Spurs, and what that means trying to predict his wishes moving forward.
Much like the Paul George situation with the Indiana Pacers, player wishes that are “set in stone” can gradually change over time. George could have easily made his way to Los Angeles, but instead decided to stay with the Oklahoma City Thunder, who he felt more connected to after a year of excellent lobbying by Sam Presti and the organization (not to mention a perceived slight from the Lakers by Paul).
That roadmap will be the one to follow for Ujiri, who will need to crib from Presti’s game plan for keeping Paul. How to figure out how to apply what Presti did to Leonard will be Ujiri’s biggest test of the season.
In the end, Leonard is an enigma. What he wants is ultimately unknowable, and the nature of free agency in the NBA is too weird to make declarations with any kind of certainty. For now, all the Raptors can do is try to make Leonard feel wanted, healthy, and like a winner.
As we’ve seen with Leonard before, anything outside of that is a toss-up.