Five Big Questions Surrounding Kawhi Leonard's NBA Free Agency

Kawhi Leonard holds all the cards in NBA free agency. Will the NBA champion return to Toronto or will he head home to Los Angeles? The Crossover analyzes these questions and more ahead of his big decision.

It would certainly be unprecedented for the Finals MVP to leave his current team less than a month after hoisting the Larry O’Brien trophy, but we’ve long known Kawhi Leonard is a different dude. Toronto’s resident ‘fun guy’ is nearly impossible to get a read on, light on words and even lighter on expression. It wouldn’t be a surprise for Masai Ujiri to have no idea where Leonard is headed. The tea leaves are meaningless to read. Don’t expect a glossy magazine piece or heartfelt essay from Leonard. If he bolts from Toronto, the message will be clear from both sides: Thanks for the memories.

While we’d be a fool to parse Leonard’s actions for free agency clues, we can set the terms of debate for his next move. There are a number of free questions that loom over Leonard’s free agency, the answers to which could sway the decision for the league’s preeminent free agent. With less than a week remaining until Leonard’s free agency, we at The Crossover identified five key factors that could swing the NBA’s balance of power for years to come.

Can We Trust Toronto’s Future?

Leonard’s return to Toronto would secure the Raptors’ spot atop the top contenders for the 2020 title, though are we convinced their championship window will stay open much longer? Toronto is in no position to create a superteam, and a large share of the team’s core is trending toward their late 30s. Leonard could run the risk of spending his prime with a creak supporting cast as Milwaukee and Philadelphia ride their youngsters to the conference crown. Leonard may be the King in the North forever. His time as King of the NBA may be far shorter.

Toronto will face a turning point next summer. Kyle Lowry and Serge Ibaka both come off the books, as does Marc Gasol assuming he opts into $25 million with Toronto. It’s possible Gasol opts out and constructs a multi-year deal to stick with the champs. Yet there’s minimal chance he enters the free agent market. Gasol’s best bet is still the opt in, giving the Raptors a third expensive contract expiring in 2020. 

Such a clean timeline provides a strong outlook into the next decade. Even if Toronto retains Leonard, it’s not beholden to an older core for long. The Raptors could chase the 2020 title with Lowry, Gasol and Ibaka, then pivot in July with Leonard, Siakam and sizable cap space. The Raptors’ future is murky. Their flexibility remains a key asset in constructing a winner into the late years of a potential long-term deal with Leonard. 

Are there Alternative Contract Options?

We’ve covered Leonard’s options if he stays in Toronto long-term, but is the full five-year max a given? We’ve seen both LeBron James and Kevin Durant sign short deals, keeping free agency close in case their respective situations go south. Leonard could take a similar route. 

Such a move might prove prudent from a winning standpoint. Toronto can strike when the iron is hot in 2019-20 with Golden State potentially out of the picture and Leonard can sign a one-year deal with an additional option. Leonard could also finally bolt to the Clippers if their haul of assets nets another big name. Leonard keeping his options open will maximize his championship window. 

Suggesting a one-and-one deal requires a short memory, though. It was just 11 months ago when Leonard joined the Raptors following a nine-game season in San Antonio. Leonard landed on Zaza Pachulia’s foot one year prior and missed the rest of the 2017 Western Conference finals. Durant’s ruptured Achilles could very well spook free-agent classes for years to come. Considering Leonard’s injury history, it’s hard to imagine him signing a short term deal in Toronto or any another location.

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How Big is the Finals Factor?

Toronto of course earns some points with Leonard for, well, winning the damn Finals, but just how much will the June memories sway Kawhi’s decision? The Raptors' love for one another after winning the title was undeniable; there was no smile and wave for the cameras. Kawhi pulled off an extended standup-comedy routine by his standards while tipsy Marc Gasol was an undeniable delight. Saying goodbye under such circumstances has little historical precedent outside of retirements. Would Leonard’s decision be different had the Raptors lost Game 3 and Game 4 to the Bucks? The current reality can only help Toronto’s pitch. 

Can Jerry West Conjure Some Magic?

The Clippers didn’t have to have the horses to compete with their Staples Center partners in the Anthony Davis sweepstakes, especially considering the pick haul surrendered by Rob Pelinka. But there may be some appealing trade options left. The Clippers’ current core is an exciting group. As currently constructed, though, it may fall short of title contention, even with Leonard. One more trade could help alter his free agent decision. 

Who remains on the market for Los Angeles? The only obvious trade option is Bradley Beal. There’s skepticism Washington will part with the two-time All-Star and Ted Leonsis favorite, but if he is in fact available, Los Angeles can provide an intriguing package including Shai Gilgeous-Alexander. 

Things aren’t much clearer on the free agency front. Tobias Harris was traded away from the Clippers already and Khris Middleton is a more likely fit to run it back with the Bucks. DeMarcus Cousins isn’t the answer and there is little Kyrie Irving buzz. Maybe a mystery free agent arises (Kemba Walker?) to add a dose of All-Star talent next to Leonard. West and Co. will do their due diligence. Regardless, Leonard doesn’t seem to be in the recruiting game like the Irvings of the world. He could come to the Clippers as he entered Toronto: A one-man wrecking crew eyeing the Finals. 

Los Angeles or Bust?

Leonard’s foray north was originally identified as a hard rental last July. With one year remaining on his contract, Leonard was expected to thaw out as soon as possible after a short stint in Toronto, allowing Ujiri and Co. to hit a hard reset button as the franchise moves to the next decade. Will a title change the calculus, or does the sunshine of Los Angeles prove too alluring? The pull of home can supersede a championship. Perhaps it could be Leonard’s deciding factor. If the sunshine is calling, what is Ujiri to do?