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TSN Raptors Reporter

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TORONTO – What did we learn about Kawhi Leonard, the person, in his first – and perhaps only – season as a Toronto Raptor?
 
Quite a bit, it seems. That probably speaks more to how little we knew about him during his seven-year run in the shadow of Hall-of-Fame teammates and a legendary coach with the Spurs.
 
He’s extremely memeable, for one. He’s got a dry sense of humour and a hypnotic laugh. He’s even in on the joke, as we recently found out. Remember, he’s a fun guy.
 
However, relative to other superstars in the NBA, Leonard remains something of a mystery. He’s a private person by nature, introverted and soft-spoken. He’s a closed book, which makes his impending free agency truly fascinating.
 
Leonard will opt out of the final year of his current contract this week – an expected formality, which will make him an unrestricted free agent when the negotiation window opens at 6 p.m. ET on June 30. 
 
From there, players and their representatives are able to meet with teams and begin to discuss the terms of a new deal. That’s when the news of signings will start to trickle in, although they can’t be made official until the league’s moratorium is lifted at noon ET on July 6.
 
What does Leonard value most, what are his top priorities, and what will drive the decision he’s about to make? Outside of the man himself, and the small, tight-knit inner circle he keeps, nobody knows for sure.
 
We’re about to learn a whole lot more about the inscrutable superstar.
 
***
 
Like the rest of us, team president Masai Ujiri is playing the waiting game. The Raptors are confident in their chances of keeping Leonard and have been for a while, as TSN reported in March, but that confidence isn’t based on any indication they’ve gotten from the player directly.
 
It stems from the knowledge that they’ve done everything they could to tip the scales in their direction over the last 11 months.
 
Leonard didn’t have a strong opinion of Toronto – one way or the other – when they traded for him last July. The reports he had no interest in playing for or staying with the Raptors were overblown. He went in with an open mind, but the franchise had a long way to go to win him over.
 
At the time, Ujiri insisted it wouldn’t be an oversell, and given Leonard’s personality and falling out in San Antonio, that turned out to be the right approach. The Raptors got to know him; they treated him well and earned his trust with the way they managed his workload throughout the season. When he could play, he did. When he felt he couldn’t, he sat out and nobody questioned it.
 
They won a championship together. The city and the country of the Canada showed him how big his profile can grow here in the months leading up to it, and then again over the weeks since. 
 
According to a recent ESPN report, the Boston Celtics and Philadelphia 76ers were both skittish in the Leonard sweepstakes last summer because they were certain he’d end up in Los Angeles. However, Ujiri saw an opportunity and rolled the dice. This is why you do it.
 
It’s one thing to sit in a room with a player for two hours and make your case – tell them what you have to offer and then hope they choose you. It’s another to spend a year showing and proving it to them firsthand, especially for a team that’s confident in its culture as the Raptors are in theirs.
 
It’s the Oklahoma City Thunder blueprint, only they flamed out in the first round and still managed to win over Paul George. The Raptors won a title with Leonard and it’s hard to imagine anybody executing the one-year recruitment plan any better.
 
When they sit down with Leonard and his camp over the first few days of free agency, their pitch will be simple. They’ll remind him of what they were able to achieve together and how much he means to an entire nation, and then lay out a plan for their future – this is how we won and this is how we’ll continue to win with you. 
 
In addition to Ujiri, general manager Bobby Webster, Drake and Alex McKechnie – the team’s well-regarded director of sports science and architect of the now-famed load management program – are expected to feature prominently in the meeting, according to sources.
 
Still, Leonard doesn’t seem like the type to be swayed by a meeting, regardless of how many he ends up taking. If he hasn’t made up his mind already, he’s at least familiar with the factors in play. It might just be a matter of weighing his options and determining what’s most important to him.
 
The Raptors can offer him more money than anybody else and a chance to repeat as champions, on top of the mutual trust they’ve built and the way in which they’ve prioritized his health. 
 
The Clippers can offer geography – a chance to play in a warm climate in Southern California, where he grew up. While he undoubtedly values money, winning and trust, maybe he decides that quality of life is more important to him and he would be happier playing close to home.
 
That’s what makes Leonard so unpredictable. It’s impossible to have a sense of which way he’s leaning without knowing his criteria for making this huge, life-changing decision.
 
***
 
It’s also a franchise-altering decision. 
 
With the trade that sent Leonard to Toronto a year ago, the Raptors went from a very good, perennial playoff team to an immediate championship contender. That’s how good he is and that’s how important superstars are in the NBA. Their hopes of continuing to compete at the highest level, at least in the short term, are contingent on keeping him.
 
If Leonard decides to stay, the Raptors can run it back next season. Kyle Lowry, Marc Gasol – who expectedly picked up his $25.6 million player option on Wednesday – Serge Ibaka and Fred VanVleet will all be in the final year of their deals. Danny Green, the only other free agent among last year’s regular rotation players, has already expressed interest in returning.
 
The Raptors hold Leonard and Green’s Bird Rights, meaning they can retain them even though they would be over the cap and well into the luxury tax. In fact, with Leonard’s max and Green on the books, Toronto would have one of the most expensive payrolls in league history. 
 
Perhaps they would look to find some cap relief by unloading a player at the back end of their rotation, like Norman Powell, who will make $10.1 million next season. However, that’s a problem MLSE isn’t likely to mind much as long as the Raps are competing for championships – the organization has made a fortune in merchandise and ticket sales over these last few months alone. 
 
In the above scenario, where Leonard (and maybe Green) is back, adding talent for next season would be tricky. They would only have the taxpayer mid-level exception of $5.7 million to spend and have to rely on the continued growth of Pascal Siakam and hope that a healthier OG Anunoby takes the next step in his third season.

Assuming Leonard stays, the question then becomes, for how long?

Toronto can offer him a fifth year on his new deal with larger annual raises each season (8 per cent, instead of the 5 per cent he could get signing elsewhere). The security of a long-term deal could make sense for a player with an injury history, and the Raptors would have happy to give it to him.
 
With over $90 million coming off the books after next season, the Raptors could theoretically chase another star in free agency, somebody to add to their core of Leonard and Siakam, who is also due for a substantial raise (he’s eligible for an extension this summer and would become a restricted free agent in the summer of 2020, otherwise). 
 
According to multiple reports, Leonard may opt for short-term control over long-term security and sign a one-and-one deal (one year with a player option for the second). That would line him up with the rest of the Raptors’ core and is less of a risk than it may seem – Kevin Durant just suffered a serious injury that will cost him a full season and he’s still expected to get max offers this summer.
 
If that’s the case, the Raptors could run it back next season and then we would do this all over again next summer, although they would have far more flexibility to build around Leonard or pivot in a new direction should he leave. 
 
What if Leonard decides to leave this summer? While that would obviously be a huge blow, it’s probably not as debilitating as most would think.
 
One of the reasons why last summer’s trade was such a coup for Ujiri is what he gave up – or, more importantly, what he didn’t give up. The Raptors didn’t part with any of their most valuable long-term assets in the deal – Siakam, Anunoby or any of their first-round picks following 2019 – meaning they’re still well-positioned to transition to the next era if they need to.
 
If Leonard isn’t back, next season would likely be the bridge to whatever comes next. The Raptors could shop the expiring contracts of Lowry ($33.3 million), Gasol ($25.6 million) and Ibaka ($23.3 million), but it’s extremely difficult to move deals that big without taking back unwanted long-term salary, and they seem committed to keeping their cap sheet clean past 2020.
 
One common misconception is that they could replace Leonard in free agency. Because of all the money owed to the aforementioned veteran trio, as well as Powell and VanVleet, the Raptors would still be over the cap. They wouldn’t have any space to use in free agency, just a couple of exceptions, including the bigger mid-level of $9.2 million.
 
In the scenario where Leonard leaves, the Raptors would likely be reluctant to spend into the tax, which – barring some cost-cutting with the current roster – might mean Green isn’t brought back either.
 
That team would feature Siakam as the primary scoring option and still be competitive – likely a mid-tiered playoff team in the Eastern Conference – albeit with a limited ceiling. 
 
Then, with only Powell under guaranteed contract after next season (plus Anunoby when they pick up his fourth-year option) and all of their first-round picks, they can essentially hit the reset button and build around Siakam.
 
That’s not exactly a doomsday scenario, but it’s also not as fun as a future that includes Leonard. The Raptors are prepared for either outcome. They have to be