Today, Kawhi Leonard turns 28 years old. Tomorrow, the free-agency negotiating period will open up at 6 p.m. ET, and the two-time NBA Finals MVP will hit the open market when officially opts out of his $21.3 million player option. He has some decisions to make as he weighs his options between now and when he is first able to sign a new contract at noon on July 6.
It won’t be surprising if Leonard is the first big domino in free agency to fall as the league waits on him. Unlike the other big names, Leonard has no current injury issues (Kevin Durant, Klay Thompson) or chemistry concerns (Jimmy Butler, Kyrie Irving). Leonard has the best winning percentage in NBA history (minimum 400 games played) at .754, surpassing Magic Johnson (.740) and Larry Bird (.736). Wherever he goes will immediately become a championship contender.
Toronto, you’d assume, would be in the driver’s seat.
The only player not to return to his team after winning Finals MVP is Michael Jordan who retired twice, after three-peating with the Chicago Bulls.
Normally money is the greatest motivator. However, Leonard already gave up the chance to get a $221 million supermax by leaving San Antonio. So, if he decides not to return to Toronto that’s a total of $80 million he could have walked away from in consecutive off-seasons.
The Raptors ostensibly will have first and last word on pitching Leonard to stay. But that alone won’t be enough to seal the deal.
With the LeBron James recruitment being the closest comp, the Miami Heat had the last word in 2014 and the Chicago Bulls had the last word in 2010 and it didn’t matter. King James signed elsewhere both times.
Adrian Wojnarowski of ESPN was one of the first to report that Leonard’s focus is on Los Angeles.
Stephen A Smith recently reported the Los Angeles Lakers should be considered a credible option along with the long rumoured Los Angeles Clippers. Marc Stein of the New York Times feels the Lakers are the biggest threat and only landing Durant would help the Clippers.
But Leonard is the biggest enigma in sports because nobody knows what he wants and what motivates him. It’s refreshing Leonard’s camp doesn’t leak news to the media or make followers decipher the subliminal meaning of emojis. In an era when the tampering process is public and extended to holding franchises hostage, Leonard doesn’t engage in the normal free agency, silly-season trappings. Leonard’s free-agency handling is admirable but also tough to handicap.
Whenever I’ve had a tough decision my father implored me to chart out the potential pros and cons. Here’s a list breaking down the negatives and positives of Leonard’s biggest suitors to examine what he might be weighing. But let’s be honest, we all have no idea.
Los Angeles Clippers – Con
Anything the Clippers pitch would be in the hope of approximating the feat Leonard just did in Toronto. Everything the Raptors implemented would be the Clippers’ blueprint, down to even style of play and roster construction.
It might be an issue that Raptors fans are too involved. On the otherhand, Clippers don’t have fans. Clipper nation is an ironic term as the Clippers are by far second fiddle in the marketplace, meanwhile, the Raptors are the basketball team of a nation. The UCLA Bruins basketball program is more intensely followed and covered when they are good than the Clippers. Hard to settle for that after being adorned by over a million people at a championship parade.
Selling as a Clipper
The stigma that Leonard can’t sell merchandise in Canada is now gone as his shoes and shoes were sold out in minutes both in store and online every time New Balance released an allotment throughout the playoffs. But can he sell shoes to a fanbase as a Clipper? Especially at the same time as James and the Lakers are good? Chris Paul and Blake Griffin both captivated fans during the Lob City era, but that didn’t translate to the shoe or jersey sales you’d expect from all-star level play in L.A.
Can you imagine Steve Ballmer and Leonard alone in a room? I’m not sure there are two more opposite people involved in the NBA. Let’s just say Ballmer is very intense but in a loud way not in the understated way Leonard is. When you google Steve Ballmer and type a “c” after his name, the search autocompletes to “crazy,” not championship. Ballmer isn’t in the background barely seen and never heard like Larry Tanenbaum.
Los Angeles Clippers – Pro
Strong core and culture
The Clippers just took the Durant-led Golden State Warriors to six games in the first round. If you add Leonard and another max player the Clippers are an immediate championship contender. The Clippers could sell him on the fact he could become the first player to have Finals MVP on three different teams.
The Clippers have schemed and waited patiently for this exact moment. They don’t have any bad contracts on the books, and every move that has been made in the Ballmer era has either added assets, cleared cap space or both. Due to the collective bargaining agreement, Ballmer has a ceiling on players’ salaries, so he’s decided to make his competitive advantage executive pay. The Clippers front office boasts president of basketball operations Lawrence Frank, GM Michael Winger and consultant Jerry West. Winger is so determined to stay with the Clippers he turned down a promotion with the Minnesota Timberwolves to be their president of basketball operations. West’s voice, in particular, is important. The Lakers’ and Grizzlies’ front offices struggled after he left. Time will tell how the Warriors fare without him advising Bob Myers. In the Bay area, West was a big part of the Durant recruitment, and one of the reasons the Warriors balked on a trade of Thompson for Kevin Love in 2013.
With the Clippers young talent, championship-winning coach in Doc Rivers, incoming draft picks, cap space and beefed up front office, they are in line to compete for a while if they can land a star or two to lead the way.
The Clippers offer Leonard employment close to his home in southern California. In January, Leonard reportedly bought a $13-million mansion in San Diego. As Toronto Maple Leafs fans learned last July with John Tavares, sometimes the draw of going home is enough.
Los Angeles Lakers – Pro
Leonard would literally have no media pressure as a Laker. Leonard has been a reluctant star in terms of his desire for the limelight. He’s always cordial and accommodating, but it’s clear the media side of the business is an obligation not an opportunity in his mind. In Los Angeles, that burden would be lifted as LeBron James will always command the biggest scrum and the most questions. Leonard could fly under the radar in plain sight and concentrate all his energy on the part of being a pro he likes, playing basketball.
Usage Rate Reduction
The benefit of playing with James and Anthony Davis would be Leonard’s usage would come way down from the 30.3 it was last season. Leonard could preserve his body even more and see less of the loaded defences he experienced in the playoffs with Toronto. Bringing that usage down would be a preventive way to ensure he stays health and enjoys a long career.
Los Angeles Lakers – Con
After working his way back to the status where he is considered one of, if not the best player in the world, is Kawhi Leonard really going to be a three and D spacer? Why would Leonard want to watch James and Davis run pick and rolls while he stands in the corner providing offensive gravity. Neither James or Leonard specialize as off the ball players. Leonard got to take all the big shots with Toronto and got the majority of the credit when it won. Irving learned that even when you do get the chance to take and make big shots, all the credit goes to James. Players are often willing to sacrifice when they have yet to win a championship and/or they are ageing, not in their prime coming off a title.
Leonard is building a legacy as the NBA’s Robin Hood. He’s been the super team, dynasty killer on two different occasions. It would be off-brand for him to join a dynasty with the most iconic franchise in the sport.
The Lakers have been a soap opera this off-season. From Magic Johnson’s impromptu resignation, to the stories about their toxic culture, to Rob Pelinka’s revealed untruths and misremembering’s. Rob Pelinka and Jeannie Buss aren’t exactly who any star would feel confident entrusting their future with. And the drama may not end as the coaching staff is stocked with two assistants with previous head coaching experience as ready-made replacements in the event Frank Vogel fails. That’s not an ideal working an environment for a team where anything but a title will be a letdown. Leonard is the league’s most drama-free superstar so the reality show that is the Lake show isn’t a good fit. On the contrary, in Toronto, anything in addition to the title he delivered last season is extra credit.
Toronto Raptors – Con
Raptors fans have no chill
There is a downside to being beloved by a country, you have nowhere to hide in that country. Since bringing the Larry O’Brien trophy to Canada, he’s been followed and photographed everywhere from Niagara Falls to on vacation Barbados. The Kawhi stalking got so bad the mayor and the Raptors superfan had to call a press conference about it. For someone as private as Leonard, being adored could get old real fast. On the flip side in LA, there are so many stars everywhere, the sighting of Leonard isn’t going to set off alarms.
The Clipper billboard to recruit Leonard shouldn’t have said Toronto is in Canada it should have said Toronto is cold. There is nothing Masai Ujiri can do to bring the Pacific Ocean to Toronto and make it sunny every day. Despite what Lou Williams has to say the biggest obstacle for Toronto in it’s pursuit of Leonard is that it resides on the Eastern Seaboard. Leonard is a self-proclaimed “garage-to-garage,” guy so it’s not like he’s shivering and waiting for public transit like I am. But when you’re born in a warm climate and have only ever lived in one your entire life, it’s more than reasonable to want to return to one as soon as possible.
Toronto Raptors – Pro
The Raptors offer the long-term security of a five-year, $190-million deal ($38 million per year), while the Lakers, Clippers, or any another team, can only offer $140 million over four years. Given his previous injury issues, Leonard might be inclined to take the guaranteed money up front.
Leonard could sign a two-year or one-year contract with a player option That would allow him to run it back and chase another ring with the Raptors. That way he’d be in line to make even more money if he signs a long-term deal in 2021, when he will have 10 years of service and thus is eligible to receive 35% of his team’s cap.
Leonard averaged career-highs in scoring and minutes played per game last year with Toronto. He’s in a system catered to his strengths, with players who adequately balance supporting him and giving him space to dominate. Those factors aren’t a given with the Clippers and are doubtful with the Lakers.
Entering the playoffs, the starting lineup of Kyle Lowry, Pascal Siakam, Leonard, Marc Gasol and Danny Green logged just 161 regular-season minutes in 14 games. Part of the reason they got better as the playoffs went on is because they were still learning to play together. The championship level they played at isn’t their ceiling. The continuity that Toronto provides makes a title for Leonard in 2020 the most likely if he stays put.
We The East
The Eastern Conference provides an easier road to the Finals than the West.
The rest of the East is descending. The Boston Celtics look like they are going to lose two stars and both their point guards in free agency. The Philadelphia 76ers have three starters that are free agents. They might lose all three, but they certainly can’t keep all three and stay cap compliant.
The Raptors, on the other hand, finished the season as the best team in the East and are getting better.
In addition to Leonard, Green, Patrick McCaw and Jeremy Lin are free agents this summer.
Most of the Raptors will have their contracts expire by next summer, except for Norman Powell (2022) and OG Anunoby (2021).
With Lowry, Gasol, Ibaka and VanVleet expiring, that’s over $90 million coming off Toronto’s books in the summer of 2020. Siakam, Powell and Anunoby are all under contract for 2020. Siakam will likely get even better as the vast majority of NBA MIP winners go on to become all-stars. Anunoby was expected to take the leap Siakam took last year, but was dogged by injury and personal issues
If Leonard wants a team with a bunch of roster spots and cap space to recruit his friends, he doesn’t need to go to the Clippers to get it. He can get that in Toronto, all he has to do is wait a year.
The two things Leonard mentioned he wanted in his career were health and a chance to win a title. In 2019 Toronto delivered on both. Leonard played only 60 of 82 regular-season games this year. It would be prudent to manage his load wherever he goes to make sure to protect the investment. But only one franchise cannot just talk about it hypothetically – they’ve done it. The Raptors and director of sports science, Alex McKechnie, not only handled Leonard’s health beautifully they incorporated his own medical team and his wishes into their plan.
The fact Ujiri stayed in Toronto is a good starting point. It would naturally be a lot harder to sell Leonard on returning if Ujiri jumped ship to the Washington Wizards or any other franchise. When Ujiri is selling Leonard on the virtues of the situation in Toronto, he can do so with the credibility as he’s rebuffed multiple lucrative opportunities to leave. The other credibility Ujiri brings is his body of work. The Raptors under Ujiri since 2013-14, have the fourth-best wins-loss record in the NBA at 321-171 and the fourth-most playoff wins with 37.
King of the North
In Toronto, Leonard isn’t just playing for a city or even a state he’s playing for a country. The notion his greatness is hidden in Canada isn’t correct. The 2019 NBA Finals combined audience in the U.S. and Canada is was up 11 per cent compared to 2018. In Canada game six of the Finals was the most-watched NBA game ever as 56 per cent of Canadians tuned in for part of the 2019 Finals. When his New Balance shoes in the Raptors colourway are selling for more than it cost to attend a game or even attend a year of university, it’s clear being in Canada is not bad for his brand but quite the opposite.