Has there ever been a career like Kawhi Leonard’s?

No player this century has embodied the highest highs and lowest lows of superstardom, or seen the peaks and valleys of their public approval rating undergo as much turbulence as he has. 2019 saw him hit an unforgettable game-winner and become the best player in the world by force of will. And not five years later, he has gone from one of the league’s most vaunted winners to a player known more for injury-laden flameouts and disappointment on undoubtedly the NBA’s most cursed franchise.

Thursday saw Leonard declared out indefinitely to start the 2024-25 season, writing another cruel chapter in his book of missed opportunities. With the Los Angeles Clippers gutted of talent and bereft of future assets, it seems impossible that Leonard will lead this team to the promised land his arrival — alongside Paul George — hinted might be possible back in 2019. His legacy of two rings, two Finals MVPs and one of very few individuals to actually hold the best-player-alive belt now seems overshadowed by an incalculable string of injuries and failures. And if the 33-year-old doesn’t mastermind a triumphant final act, his sterling resume may somehow go down as a tragedy.

Leonard’s 2019 season was a religious experience. In a world with LeBron James, Stephen Curry and Kevin Durant all tearing the league to shreds, Leonard just went and declared himself the best player in the NBA without asking anyone for permission. He was dominant, destructive, and seemingly came out of nowhere. The Toronto Raptors took a massive risk with his injury history and expiring contract, but Leonard somehow made it pay off with the franchise’s first — and so far, only — title.

I only remember where I was for two free agent decisions ever: I was sitting on my porch in New Hampshire when Kevin Durant posted “My Next Chapter” in 2016, which created the greatest lineup of all time. And then on June 10, 2019, I was at my friend Michael’s house when Kawhi Leonard — the best player in the world at the time — chose the Los Angeles Clippers, and brought Paul George along with him. I can still hear Chris Vernon on the emergency episode of The Mismatch, saying “While we were all sleeping, Kawhi Leonard conducted an ORCHESTRA!”

Today, that season feels like a glorious oasis in a desert of injury-ridden disasters, from his final few years on the Spurs ending in bitter disagreement over his injury rehabilitation to his recent half-decade of underwhelming in Los Angeles. It would be easy to argue that his 2014 and 2019 rings and Finals MVPs vindicate all of this, with best-player-on-a-championship-team usually being all it takes to cement a career as “complete.”

But I’d argue that’s not the case. Leonard has now been a superstar-level player for a decade on three different teams, but his most personally orchestrated act — the Clippers homecoming — has been mired in failure and injuries. He was drafted by a legendary Spurs team that developed amidst pre-existing team success, and traded to a Toronto team he did not necessarily want to be on, but still made the most of it. His real personal decision was the Clippers move, with an ultimatum that if Los Angeles could acquire Paul George, he would play for them.

It was his “The Decision”; his “My Next Chapter.” Leonard, James and Durant’s moves came in almost exactly the same context: the best player in the world creating a super team to presumably run the league for the foreseeable future. But James and Durant’s moves yielded two rings each. Leonard’s has been an injury-riddled hell.

I’d argue this is the defining period of his career, not San Antonio or Toronto, and should thus be the first sentence of his legacy. His championships can’t totally wash out the bitter taste of the last five years, and save for some unforeseen heroics, that’s unfortunately the way it will stay. He has now signed over $400 million of contracts with the Clippers, who will almost certainly end up remembering him as a harbinger of disaster, rather than the savior he appeared to be.

None of this is about blame. Injuries are impossible to predict, beyond knowing certain players are injury-prone. After 2019, Leonard probably should have been in the conversation with Durant and James in a triumvirate of forwards for their generation. But his lower-body prevented that legacy, much like it did for Bill Walton, perhaps the best comparison for his career so far; a spectacular solo ring and another as a key contributor on a generational team, but injuries and “what if?” will always be in the first sentence of any Walton conversation.

It may not be Leonard’s fault, but injuries have ruined what could have been one of the five greatest careers of this generation. If things stay as they are, it will make it impossible to look at his resume, which is undeniably incredible, without also wondering what could have been. He is still a Hall of Famer, but his plaque in Springfield can no longer be solely defined by the rings that got it made. And with this latest nebulous setback, the only certainty around Leonard’s future is that the first sentence on that career epitaph will now always be “what if?”