Hindsight has a clarifying effect. When viewed in reverse, every decision is a puzzle piece that fits neatly into place and has a clear causal relationship. But in the moment, there’s no way of anticipating a desired outcome with any kind of certainty. Make no mistake: when the Toronto Raptors traded for Kawhi Leonard last summer, it was a major gamble.
Kawhi had sat out all but nine games the previous season, the circumstances of which were murky at best. First, there was the question of his health and whether there might long-term consequences that could possibly derail his career entirely. Perhaps even more unnerving was the way his character was being maligned by a certain subset of fans who believed he was playing hardball with the Spurs and had outgrown the proverbial koi pond in San Antonio.
His silence on the matter didn’t help his case. But as always, Kawhi was content to let his actions do the talking, fully self-assured that any lingering trepidation about his health or his attitude would evaporate once he got back to playing basketball at an elite level. He was right, and that happened almost immediately. From the start of the season, Kawhi looked every bit like the former Defensive Player of the Year and Finals MVP he was in San Antonio before his injury.
Still, there was the messy situation involving Kyle Lowry and his fraying relationship with Raptors management. Lowry wasn’t just heartbroken that the front office traded his best friend and long-time running mate, DeMar DeRozan. He felt betrayed. In the immediate aftermath, Lowry claimed that he’d been given assurances that team brass wouldn’t break up the duo. And early on, he wasn’t about to let Masai Ujiri off the hook, nor was he prepared to publicly endorse Kawhi. At least, not at first.
It was a palpable risk that they may have alienated their relationship with Lowry to the point that it was beyond repair. But success and goodwill make perfect bedfellows, and it didn’t take long before the Raptors’ ascension in the East pushed it all further and further into the background.
Still, Kawhi and the Raptors needed plenty of load management protocols, not to mention a few (literal) lucky bounces of the ball to overthrow the Warriors and win the first NBA championship in Raptors history. Yet even then, his future with the organization is anything but certain.
Surely, winning a title must’ve doubled or quadrupled their odds of keeping him. But nothing is a given, and there’s still plenty of work to be done to convince him that it’s in his best interests to sign a long-term deal to stay in Toronto. After their Game 6 win on Thursday, Kawhi was as inscrutable as ever about his future.
It also doesn’t appear that Lowry will spend much time or effort trying to recruit him, despite making it abundantly clear that he wants him to stay.
The implication, of course, is “how much more convincing do you need?” If winning a title — and blowing up a dynasty in the process — in your first go-around with your new team isn’t enough incentive, there’s no amount of sales-room pitching that’s going to tip the scales.
Whether he re-signs or not, there’s no longer any question about whether it was worth the risk. The Raptors got their championship. Trading for Kawhi wasn’t about the future, and their future doesn’t hinge on him. Recent history has shown the trappings of playing it safe and the misguided reluctance to “leverage your future” instead of seizing the day (hello, Lakers).
It isn’t incumbent on Lowry to plead his case to Kawhi. Like he said, that’s never been his style. Besides, free agency is still more than two weeks away. They should both just live it up while they can, and forget about all that other stuff for a minute. There’ll be plenty of time to stress out about it soon enough.