Toronto Raptors' Blueprint to Re-Signing Kawhi Leonard in 2019 NBA Free Agency

Dan Favale@@danfavaleFeatured ColumnistOctober 19, 2018

MONTREAL, QC - OCTOBER 10:  Kawhi Leonard #2 of the Toronto Raptors reacts against the Brooklyn Nets during the pre-season NBA game at the Bell Centre on October 10, 2018 in Montreal, Quebec, Canada.  The Toronto Raptors defeated the Brooklyn Nets 118-91.  NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement.  (Photo by Minas Panagiotakis/Getty Images)
Minas Panagiotakis/Getty Images

The Toronto Raptors are not beginning their relationship with Kawhi Leonard under any illusions.

They acquired him from the San Antonio Spurs as a rental. They'll try to turn this partnership into something greater, something permanent. But the prevailing assumption upon Leonard's arrival was that his stay would be a temporary one.

For as long as Toronto's season lasts, that shouldn't change. It can't change.

This situation parallels Paul George's chance-relocation to the Oklahoma City Thunder before last season—only with more twists. Leonard is unreadable, his intentions not yet entirely clear.

He (likely) dipped on a five-year designated player extension worth more than $220 million. He initially didn't want to play in Toronto, per Chris Haynes, then of ESPN.com. He has eyes for Los Angeles, as reported ad nauseam, but not necessarily for LeBron James' Lakers, according to The Ringer's Kevin O'Connor.

Is Leonard most concerned about winning? About building his brand? How about just leading a franchise all his own, beyond the shadows cast by Tim Duncan, Manu Ginobili or Tony Parker? 

On paper, the Raptors can offer him a combination of everything, along with a fifth-guaranteed year in his next contract to boot. Smart alecks will point out that making the Eastern Conference Finals and NBA Finals will give Toronto the inside track on keeping Leonard. Winning sells. What a novel concept.

Our blueprint for the Raptors to keep Leonard journeys beyond the obvious. They have a chance to keep him—a legitimate one. Hovering around the championship discussion is part of it. But their season-long recruiting pitch is more complicated than when and where the season ends.


Superstar Treatment

MONTREAL, CAN - OCTOBER 10: Kawhi Leonard #2 of the Toronto Raptors warms up prior to a pre-season game against the Brooklyn Nets on October 10, 2018 at Bell Centre, in Montreal, Canada.  NOTE TO USER: User expressly acknowledges and agrees that, by downl
Mark Blinch/Getty Images

Leonard may not be as low-upkeep as advertised. Before orchestrating his exit from the Spurs, he apparently grew jealous of the treatment and promotion fellow superstars received from their teams, according to the San Antonio Express-News' Jeff McDonald.

What has always been perceived as reluctant superstardom from Leonard might actually be hushed resentment, however slight. Then again, maybe not. Toronto is banking on the latter. As team President Masai Ujiri told reporters:

"There is nothing we are going to do different. We are going to be ourselves. I think the situation with him in San Antonio, which I don't want to talk about because I don't know much about it, but he's a quiet kid. That's his nature. We can't all be the same kind of people. But he is as engaging as he would want to be, and he's very interesting. There is no maintenance with him. There are no tons of people around him. His [focus] is on basketball, which is what you want. He is a basketball junkie."

Managing Leonard without exception makes all kinds of sense. Free-agency recruitment isn't about eight to 10 months of grand gestures and uncharacteristic attention. Desperation has a distinct stench. Toronto doesn't want to come off as the needy, "So, where exactly is this going?" end of the relationship.

Still, the Raptors should not be above empowering Leonard to break out of the Spurs-shaped box. Establishing him as the face of the franchise is easy. Coaxing him into feeling more at home is the bigger challenge. His time in Toronto should be punctuated by heightened visibility, more personality and, above all, an extra sense of obligation.

To their credit, the Raptors appear to be killing this part of the equation early on:

Ryan Wolstat @WolstatSun

Danny Green said today he has never seen Kawhi Leonard this vocal. Nurse had talked yesterday of Leonard's leadership. Green isn't sure if it is a seniority/age thing (wasn't going to say much around Duncan, Manu, Parker, etc.) but said he definitely seems comfortable here.

It sounds corny, but this stuff matters. After spending so much time in San Antonio's culture, Leonard is almost a blank canvas. He isn't just escaping the legend of his predecessors. He's entering an entirely different environment in which front-facing spunk isn't as atypical or taboo.

No, the Spurs are not a militant organization. Outwardly, though, they're more all-business than most. The Raptors have done a better job of broadcasting their lighter side. We wouldn't be waiting for the Kyle Lowry-DeMar DeRozan buddy-cop movie otherwise. They have the track record and locker-room personalities to lure Leonard out of a shell that, as evidenced by his envy for other marquee names, might not be so impenetrable. 

Count Leonard's first-ever (but not really) laugh as genuine, and Toronto is off to a good start here as well:

TSN @TSN_Sports

Some smiling and laughing from Kawhi Leonard during his introductory press conference with the Raptors. https://t.co/uYNYldpwDC

Chemistry with Kyle Lowry

LAS VEGAS, NV - JULY 27:  DeMar DeRozan (L) #35 and Kyle Lowry #43 of the United States attend a practice session at the 2018 USA Basketball Men's National Team minicamp at the Mendenhall Center at UNLV on July 27, 2018 in Las Vegas, Nevada.  (Photo by Et
Ethan Miller/Getty Images

Worrying about Lowry's long-term response to Leonard's arrival takes it a step too far. He and DeRozan are BFFLs, and his evasiveness immediately after the trade was less than ideal:

Tim and Sid @timandsid

When asked about Kawhi Leonard at USA Basketball minicamp today, Kyle Lowry says, "I don't know if I've spoken to him." https://t.co/o4Yd2iHNrD

But Lowry is a professional. He's a competitor. Toronto has to be careful about how it juggles two franchise stars. Fractured egos are an ever-present liability. But Lowry will see the value of playing with Leonard. He's already backed off his crypticness:

Josh Lewenberg @JLew1050

Lowry's been paired with Leonard in almost every drill in camp so far, said they're starting to learn each other. "We have to be on the same page and I think we're gonna be on the same page. He's a heck of a player."

Ensuring Leonard and Lowry forge an on-court bond that lasts longer than a honeymoon is the Raptors' more pressing concern. Toronto needs them to feel like they need one another. 

That essentiality will be easier to create on Lowry's end. He spent more time off the ball last season and routinely ceded touches to DeRozan in crunch time. He won't flinch at Leonard or anyone else playing an expansive offensive role, and as he contemplates his fast-approaching twilight, he should appreciate having a Defensive Player of the Year, in-your-face stopper assuming so much of the half-court burden.

Whether Leonard feels a functional attachment to Lowry is a different matter. He'll welcome the spot-up looks Lowry manufactures for him by leveraging his bully-dribble penetration and pull-up jumper, but Leonard is more than a half-decade his point guard's junior. He has to see the 32-year-old's game aging exceptionally well to envision a future in Toronto.

That, or he'll need to believe one of the Raptors' NBA toddlers—namely Pascal Siakam or OG Anunoby—will develop into No. 2 material.


Blockbuster-Sized Open-Mindedness

TORONTO, ON - SEPTEMBER 24: Kawhi Leonard #2, Masai Ujiri and Danny Green #14 of the Toronto Raptors pose for a portrait at a press conference after media day on September 24, 2018 at the Air Canada Centre in Toronto, Ontario, Canada. NOTE TO USER: User e
Ron Turenne/Getty Images

Finding another star to join Leonard for the bigger picture is not something that should necessarily wait.

Lowry isn't getting any younger no matter how well he plays this season. He will be 34 when he enters free in 2020. Anunoby and Siakam are more likely superstar role players than full-fledged superstars (Siakam has already made me regret that sentence.) The Raptors aren't snaring any primo draft choices if they're busy contending for Eastern Conference bragging rights. They have no clear path to cap space before 2020.

Waiting for Leonard to commit before making another big move is the safe play. Toronto shouldn't be trying to play it safe now. Landing Leonard entailed just the opposite. Convincing him to stay could require more of the same. 

It just so happens the Raptors are set up nicely to monitor the disgruntled-star market. Packages built around some combination of Anunoby, Siakam, Norman Powell, Fred VanVleet (trade-eligible after Jan. 14), Delon Wright and future picks provide a nice mix of upside, immediate help and agreeable salary filler. Toronto also has Danny Green's expiring contract and CJ Miles' affordable deal ($8.7 million player option for 2019-20) to use as bait.

This doesn't mean the Raptors should be hocking their best assets to anyone who will listen right now. This roster deserves a chance. And a variety of other teams can easily outbid Toronto for the best potential trade candidates. 

It also never hurts to look—particularly when the Raptors are uniquely positioned to meet the demands of sellers not trying to start over.

They have the pieces to help the Minnesota Timberwolves pursue fringe relevance after trading Jimmy Butler. They can give the Portland Trail Blazers win-now depth and developing ceilings if Damian Lillard grows disenchanted with mediocrity. They can dangle inexpensive impact players if the Boston Celtics decide Gordon Hayward is a luxury they neither need nor want to try affording as they face punitive tax payments in the coming seasons. (With Kyrie Irving all but signing on the dotted line, Hayward's future is, in fact, worth keeping an eye on.)

Once more: It'll take a perfect storm of circumstances for the Raptors to add another star. Weirder things have happened—the Leonard trade itself, for instance. Ujiri is never one to sit totally idle anyway. He shouldn't start now if another dice roll increases the likelihood Toronto retains one of the five best players alive.

Look to OKC 

OKLAHOMA CITY, OK - SEPTEMBER 24: Paul George #13 and Russell Westbrook #0 of the Oklahoma City Thunder pose for a portrait during media day at Chesapeake Energy Arena in Oklahoma City, Oklahoma on September 24, 2018. NOTE TO USER: User expressly acknowle
NBA Photos/Getty Images

The Thunder are a model for the Raptors. Their situations are different; George seemed more enthusiastic about arriving in Oklahoma City than Leonard originally seemed about joining Toronto. But the end goals are spitting images of one another: keep a player who isn't supposed to stay there.

The Raptors won't give themselves a real opportunity to re-sign Leonard if they place stock in midseason tealeaves. There will be reports about how he plans to leave for Los Angeles, or about how he's suddenly intrigued by the Philadelphia 76ers, or about how he has the urge to sync up with Kevin Durant on the New York Knicks. 

Toronto needs to ignore the rumblings, all of them, and stay the course. Oklahoma City looked past speculation at last year's trade deadline and came away with a four-year commitment (player option after year three) from George in the end.

Short of Leonard mirroring Jimmy Butler's behavior in Minnesota, the Raptors have no reason to bail out early. It doesn't even matter if they're trailing the Eastern Conference's other superpowers by a startling margin. Things can turn over a few months and during the postseason. 

All hope isn't lost if they don't. The Thunder were unceremoniously bounced from the first round by the Utah Jazz. George still stayed. Leonard may not love Toronto as much as George does Oklahoma City, but even then, the dollars and cents work out in the Raptors' favor.

Forcing his way out of San Antonio already cost Leonard a five-year, $221.3 million extension. The Raptors can sign him to a five-year pact worth $189.7 million. Other teams can only offer him four years and $140.6 million. 

Money doesn't always matter to the best players. It might to Leonard. His right quad injury derailed an entire season. He will (probably) be in his 30s the next time he hits the open market. Getting his full bag could mean more to him than reaching free agency again as soon as possible and banking on his next deal. 

Whatever happens, the Raptors will always have that going for them. The temptation to cash out on the Leonard experiment might still persist. They do not have the flexibility to care. They bet on themselves by trading for him in the first place. Nothing should dissuade them from letting that leap of faith play out.


Unless otherwise noted, stats courtesy of NBA.com or Basketball Reference. Salary and cap-hold information via Basketball Insiders and RealGM.

Dan Favale covers the NBA for Bleacher Report. Follow him on Twitter (@danfavale) and listen to his Hardwood Knocks podcast, co-hosted by B/R's Andrew Bailey. 


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