TORONTO – You don’t know what you’ve got till it’s gone, as Joni Mitchell once sang.
Seven years ago, on a hot Monday afternoon in June, Kawhi Leonard was standing on a float in the middle of downtown Toronto, cradling the “Larry O-B” with one of his massive hands and his Finals MVP trophy with the other. He was smoking a cigar, dapping up Drake, and staring into an endless sea of Raptors fans.
That day, a couple members of the organization noted that they saw the cerebral superstar smile more in a few hours than in the eight months that preceded them. It was the culmination of everything he and his team had accomplished during their historical championship run, but by all accounts, he knew it also served as his farewell party.
Leonard came, he won, and he left. That was always the plan.
Expectations are the key to just about everything in life. Leonard’s lone season north of the border exceeded his expectations because, well, he didn’t expect much. It far and away exceeded the Raptors expectations because they weren’t sure he would even show up. But when he made the unprecedented decision to leave a title-winning team 18 days after the parade and go home to join the Los Angeles Clippers, just like he said that he would, nobody inside the organization was crushed. They were disappointed, sure. Some were a bit salty over how things played out during a negotiation period in which they felt they had been used as leverage. But it didn’t come as a shock.
In the years that followed, the Raptors mounted a valiant title defence that was derailed by the pandemic, were forced to relocate for an ill-fated season (that ultimately landed them the future face of the franchise), and reluctantly dismantled the rest of their championship core and opted to rebuild.
What could have been? It’s a question the Raptors have asked themselves repeatedly over these past seven years and one that Leonard has also contemplated, apparently.
The California native chose L.A. to be closer to family and friends, but he also expected to be competing for championships, like he did in Toronto and San Antonio. Instead, he learned that the grass isn’t always greener. With the Clippers, Leonard battled injuries and was at the centre of multiple controversies, including allegations of salary cap circumvention that are still being invested by the league. The Paul George deal that he helped engineer wasn’t just a flop, it might go down as the worst trade ever. Over the past seven seasons, he averaged 47 games and the Clippers only made it out of the second round once.
Last week, reports began to circulate – with one year left on his deal, the Clippers were unwilling to offer Leonard an extension and seemed ready to move on. His preferred landing spot and, reportedly, the only team he would agree to sign with long term: the Raptors?
It seemed far-fetched at first. The suspicion, even from some of the most plugged-in sources around the league, was that Leonard and his camp could be using Toronto as a means of extracting more money from Los Angeles. Wouldn’t be the first time. But smoke turned to fire, talks between the Raptors and Clippers heated up, and on the eve of Canada Day, one of the most improbable reunions in the history of professional sports came to fruition.
Leonard is heading back to Toronto, this time in exchange for Brandon Ingram, Gradey Dick, a pair of unprotected first-round picks, a first-round pick swap, and a couple of second-rounders.
The price, as it turned out, was not insignificant. According to league sources, the Raptors’ initial offer included one first-round pick and a pick swap, with a strong preference for the picks to convey over the next few years, as opposed to the distant future. What they settled on was firsts in 2031 and 2033, when Leonard will be 40 and 42 and likely retired. The pick swap is for next summer’s draft and, assuming all goes according to plan, is unlikely to matter.
It’s a higher price than they paid in 2018, when Leonard was 27 and acquired from San Antonio for DeMar DeRozan, Jakob Poeltl and a single protected first-round pick. Then again, they were flying blind; unsure of whether Leonard – coming off an injury plagued season – was healthy and willing to stay beyond the final year of his contract. This time, there’s less uncertainty. He’s coming off arguably the best season of his 14-year career and expected to sign a maximum two-year extension, which is valued at $123.7 million and will keep him under contract through the 2028-29 campaign.
Bobby Webster, who was instrumental in landing Leonard the first time, has made his first big move as a lead executive and he’s going for it. It’s a big gamble on a player that turned 35 on Monday, one with an extensive injury history, who isn’t exactly considered to be a low-maintenance star.
The bet is that they can maximize these next few years with the future hall of famer and then find a way to remain competitive in the post Leonard era, lest those picks come back to bite them later. If they can keep the often-injured forward on the court for 50-60 games per season and have him ready for the playoffs that should be enough to make them an instant contender in the Eastern Conference.
Even with a different supporting cast than the one he left behind in 2019, Leonard should fit in seamlessly. He’ll share the court with an All-NBA defender in Scottie Barnes and, perhaps, a future all-league defender in Collin Murray-Boyles – raising the defensive ceiling of a group that ranked fifth on that end of the floor last season. He’ll take pressure off Barnes and Immanuel Quickley as primary creators. RJ Barrett, another big winner of the trade, goes from expendable piece to somebody that will be counted on to carry the offence when Leonard has his inevitable rest nights.
With respect to Ingram, who came in, got healthy and re-established himself as an all-star, there was a clear ceiling on what that Raptors core could do and they came pretty close to hitting it last season. But credit to a young team and their head coach, Darko Rajakovic, who won 46 games and turned heads with their compete level in a hard-fought seven game series against Cleveland. Without it, it’s hard to imagine this situation being as appealing for Leonard.
Beyond that, there’s a level of familiarity in Toronto, for the player and the team. After all, the Raptors wrote the blueprint on how to manage Leonard and his health over the course of a season, while keeping him fresh for a full playoff run.
They’ve long believed that they have the best medical staff in the league, helmed by player health and performance guru Alex McKechnie. Leonard doesn’t trust many people, but he does trust in McKechnie. The fan base embraced him and the organization catered to his every need in an effort to make him feel at home and convince him to stick around long term. Turns out it all paid off, eventually.
Symbolically, what it represents for Leonard to return and do so of his own volition is every bit as important as the basketball fit. While his decision to leave seven years ago wasn’t unexpected, it was triggering for a fan base that has an understandable chip on its shoulder. The Raptors have come a long way in the past three decades, but the stigma is still there. There’s always been a perception that star players don’t want to play in Canada, and fair or not, perception is reality. Leonard spurning Toronto evoked memories of Damon Stoudamire, Tracy McGrady, Vince Carter, and Chris Bosh doing the same.
For all the firsts that the franchise has experienced over its 30-plus years, it has never recruited a star player in free agency. Now that traditional free agency is all but extinct in the NBA, this is as close as it gets. Not only is this a superstar saying that he wants to be in Toronto, reportedly, it’s the only place that he wanted to be and where he wants to play out the rest of his hall of fame career.
Seven years ago, Leonard sparked the imagination of an entire country. He lifted a fan base and turned the Raptors into a championship organization. His second tenure is unwritten, but even before it begins, his unlikely return has already reignited that spark. Anything is possible in this crazy league.
