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What will Kawhi Leonard’s free agency decision be based on?

Winning a title in Toronto would theoretically make it impossible for Kawhi Leonard to leave the Raptors, but the rules of free agency have changed.

NBA: Los Angeles Clippers at Toronto Raptors Tom Szczerbowski-USA TODAY Sports

Last week, Bleacher Report’s Howard Beck wrote about how strange it was to be discussing the free agency of two players who were in the NBA Finals, specifically Kevin Durant and Kawhi Leonard. Over the past decade, players who have moved in free agency have done so primarily to improve their chances of winning championship, but Durant and Leonard are already in position to win titles on their current teams.

Given that both players have already won championships and been named Finals MVP, there’s a new current of thought that stars who have already reached the mountaintop no longer need to prioritize winning.

The Clippers have been connected with Leonard since he was traded to Toronto, both because of their diligent pursuit of him in manners both legal and not so much throughout the regular season, and because of Leonard’s well-documented interest in playing near his hometown.

As the playoffs have gone on, the Clippers’ chances of getting Leonard be expected to decrease, as the superstar’s situation with the Raptors proves to be more and more conducive for contention. It would be one thing to leave a team that lost in the Eastern Conference semifinals for a better opportunity in Los Angeles — it’s quite another to leave a team that just won a title or went to 7 games in the NBA Finals. For all of the promise that the Clippers showed this season, they would be hard-pressed to match that pitch from a basketball perspective.

This isn’t to denigrate the talent of Shai Gilgeous-Alexander, or the dominance of the Lou Williams/Montrezl Harrell two-man game, or the consistency of Danilo Gallinari even as a number one option on offense — but the team Leonard is currently on is about to beat the Golden State Warriors. That’s no small feat.

Which is why it’s so interesting to hear from people like Beck and Adrian Wojnarowski earlier today that Leonard may not follow the traditional model of picking the most attractive winning situation when it comes to free agency. Woj discussed the thought processes of both Leonard and Durant on ESPN before Game 5 of the NBA Finals.

“It’s going to be on comfort, fit, where do they want to live, the marketplace. That allows the Clippers, in Kawhi Leonard’s case, to be at the forefront of his free agency.

I think having the multiple championships, especially Leonard being on the brink of his second, it changes the view.”

All the Clippers can do at this point is present their pitch — a loaded front office, talented young players, veterans who are willing to be role players, and gobs of future assets — and hope Leonard bites. In the meantime, let’s just wait and see if Leonard comes to that meeting with a little more jewelry.