Leonard, as we all know, will become a free agent following the coming season, and between reports that he didn’t want to play in Toronto and that he has his eyes firmly set on playing in Los Angeles, everybody wants to know: Will Kawhi re-sign in Toronto?
The trade stands to benefit the Raptors regardless of Leonard’s decision, but there’s no doubt the best-case scenario for the franchise would be to re-sign one of the NBA’s top-five talents and build a champion contender around him.
It’s why this upcoming Raptors season will be as much about capitalizing on a currently brief window to reach the Finals while also trying to show Leonard that Toronto is a viable long-term landing spot.
How can the team convince him to stay? These selling points would be a good start.
This one is pretty simple.
As outlined by the NBA’s collective bargaining agreement, Leonard would be able to sign a longer deal worth more money if he decides to stay in Toronto.
Next summer, the Raptors can offer Leonard a five-year contract worth $190 million — the max extension possible. Any other team’s max offer to the 27-year-old superstar would be for just four years and $141 million.
In many cases that could be a compelling enough reason to re-sign, but Leonard has already opted to walk away from nearly $30 million when he left the Spurs, who could have offered him a “supermax” deal of five years and $219 million. Needless to say, money may not be a chief motivation for him.
One of Leonard’s underlying motivations for wanting out of San Antonio was that he — and, more specifically, his camp — wanted to play in a bigger market, according to a May report.
It may seem like an odd desire given his seeming distain for the limelight, but Leonard’s talents and accomplishments open up unique opportunities that larger cities are better equipped to foster.
Aside from perhaps marketable Philadelphia 76ers centre Joel Embiid, Leonard is currently the most sought-after free agent in the NBA’s sneaker endorsement market.
He is currently endorsed by Jordan Brand with a contract set to expire on September 30 (Nick DePaula covers the details nicely here). Other brands are allowed to speak to him two months prior to that date.
Despite his unreal résumé — which includes Finals MVP and two defensive player of the year awards, joining Michael Jordan and Hakeem Olajuwon as the only other players who can say the same — Leonard hasn’t found the same level of fame as his peers on the court like LeBron James, Steph Curry or Kevin Durant. Obviously much of that is by choice for Leonard, and Jordan Brand has struggled to find a way to make it work.
An advertising campaign at the beginning of last season starring Leonard proved unsuccessful.
Leonard first signed with the company in 2013 and up until this summer earns $500,000 per year from them. He reportedly turned down a four-year, $22-million extension offer from Jordan Brand earlier this year.
Leonard has proven to be ok with leaving money on the table. Then again, being a top-five player — arguably the best in the East this season — provides a once-in-a-lifetime opportunity to cash in and build a brand.
The question is: Can he do that playing in Toronto?
That’s what the Raptors will need to prove to Leonard, especially given they are competing with a market like Los Angeles, where Leonard has long been linked to.
Toronto is no L.A in that regard, but there’s a decent case to be made.
Based on Nielsen projections, Toronto boasts the NBA’s fourth-largest media market, behind New York/Brooklyn, Los Angeles and Chicago (but the longest average daily commute! Ok, maybe they should leave that part out).
In terms of franchise value, Forbes ranks the Raptors 12th in their evaluations, up two spots from two years ago, and the team continues to grow its stature in the Toronto sports landscape.
Shoe brands in the past have been able to successfully market Raptors players. Most recently, DeRozan inked a lucrative extension with Nike that was marked with the release of his own signature sneaker. The best example, of course, is Vince Carter, who signed a major deal with Nike during his Raptors’ tenure that saw him starring in international campaigns that helped make him one of the NBA’s most marketable superstars.
Of course, Carter’s flashy smile and flashier dunks helped propel him, and it’s an advantage Leonard won’t have regardless of where he plays.
In today’s online landscape, where physical distance is less of a barrier than ever, the Toronto market should be capable of meeting Leonard’s needs.
The Canadian Shield
Juxtaposed with his reported market desires and the way his play demands attention on the court, Leonard undoubtedly prefers to fly under the radar in other aspect of his life.
That’s where the Canadian Shield may come in handy — not the 8 million squared kilometres of Precambrian rock but the notion that athletes playing in Canada can slip under the radar in the greater North American landscape.
Appearances with the Olympic teams and all-star games no doubt helped boost DeRozan’s public image in the United States, as it did for Chris Bosh as well. And while we don’t know where their notoriety would have reached without that non-Raptor visibility, perhaps playing north of the border can offer the balance of fame and privacy that a player like Leonard could find appealing.
Yes, it may be odd to include this in a pitch to Leonard if you’re the Raptors given how it can run counter to many of the points you’d want to make in the section above, but it’s at least worth considering.
The Raptors, until recently the laughing stock of the NBA, have quickly established themselves as a respected franchise with a successful track record under Masai Ujiri and the current regime.
But, frankly, after coming from the San Antonio Spurs — the consummate organization in pro sports — this one would be a tough sell for anybody. Let’s move on.
Here’s where the Raptors can make their best case to re-sign in Toronto.
Over his seven seasons, Leonard has pursued on-court success and winning over everything else. This Raptors team is going to win — a lot — with their newest superstar in the lineup.
Heading into the season, it can be argued the Raptors are neck-and-neck with the Boston Celtics as the favourites in the East — I even liked the Raptors, who tied the season series with the Celtics 2-2, to advance past Boston if they faced had each other last playoffs. The return of Gordon Hayward and Kyrie Irving to Boston’s already potent lineup boosts their stock considerably, but with everybody at full-strength, Leonard is still the best player on either team.
In the long term, Leonard could have a better chance — at least just as good — of reaching the Finals and competing for a championship in Toronto.
That is a statement you could have never really made about the Raptors at any point in their 20-plus year existence, so it feels strange to write. But I actually believe it to be true.
The Raptors are contenders this season, but there’d be no signs of slowing down in the years to come if a healthy Leonard remained on board.
If he were to suit up alongside LeBron James, the Lakers would be terrifying but would still have to get through the Golden State Warriors (who have a few more seasons of top-dog status left in them) and the West’s other tough matchups en route to the Finals each season.
The East wouldn’t be a cake-walk given the young nucleuses in place in both Boston and Philadelphia. But a Raptors roster that could feature a truly unique and formidable group of Leonard, Kyle Lowry, Pascal Siakam, OG Anunoby, Fred VanVleet, Jonas Valanciunas, C.J. Miles, Serge Ibaka and Delon Wright would be as competitive as any in the conference.
Leonard may not have wanted to leave the warmth of California for the Canadian winters, but there’s a chance he happened to have landed in one of the best situations out there.
Again, when it comes to his future plans, it’s far too early to tell. To complicate things, Leonard, who is notoriously hard to read, doesn’t seem to be motivated by the same factors as most other superstars of his calibre, as indicated by his lack of social media presence.
The Raptors are well-positioned to drive full-throttle in any direction once Leonard either decides to go one-and-done and form a super-team elsewhere, or to re-sign in Toronto and establish a perennial title threat in the East.
Still, Ujiri and Co.’s recruiting push will be among their most important moves yet because, and given the option, of course you choose the latter.