Why LA Clippers forward Kawhi Leonard creates familiar dilemma for the NBA

There’s no good way out of this.

That’s what the NBA is beginning to realize about its Kawhi Leonard predicament today. It’s the same thing the Spurs realized seven years ago.

Little by little, one painful decision has been vindicated over time.

We’ll have to wait and see about the next one.

The difference this time is that NBA commissioner Adam Silver has more folks to answer to than R.C. Buford did in 2018. Back then, the man in charge of the Spurs had to justify his decision regarding Leonard to the fan base of one franchise. Eventually, Silver will have to justify his ruling to 30 of them.

It’s a mess, and from the outside, it’s hard to look at it now without thinking the Spurs made out pretty well in retrospect.

Yes, the Toronto Raptors won the Leonard trade, along with an NBA championship banner that will hang forever.

Yes, the Spurs have failed to win a single postseason series since letting Leonard go, and currently own one of the longest playoff droughts in the league.

And yes, Leonard remains on track for his inevitable, well-deserved enshrinement in the Naismith Basketball Hall of Fame.

But if the Spurs had it all to do over again?

Are we sure there’s anything they’d change?

These days, with a deluge of scoops from investigative reporter Pablo Torre raising questions about possible salary-cap circumvention by the Los Angeles Clippers and multiple stories about alleged extravagant demands made by Leonard’s uncle, many people around the league are revisiting the story of the Spurs-Leonard split.

San Antonio Spurs forward Victor Wembanyama (1) gets his arm stuck while trying to defend Los Angeles Clippers forward Kawhi Leonard (2) during the first half of their NBA game at the Frost Bank Center on Wednesday, Jan. 29, 2025 in San Antonio. With questions regarding possible salary cap circumvention surrounding Leonard and the Clippers, NBA commissioner Adam Silver faces a dilemma all too familiar to the Spurs. (Marvin Pfeiffer/San Antonio Express-News)

It remains almost as confounding now as it was at the time. What began as an apparent difference of opinion about treatment of an injury spiraled into something irreparable, and the low-key superstar who always seemed like a perfect fit for the NBA’s most accomplished low-key dynasty decided he simply couldn’t play in San Antonio anymore.

For whatever reason, there was no fixing it. For whatever reason, the franchise that had been a pioneer in load management – and had been known as one of the most notoriously conservative teams in the league when it came to bringing players back from injury – couldn’t convince Leonard it had his best long-term interests in mind.

And so the Spurs found themselves in a spot much like the position Silver is in now: Stuck.

With nothing but undesirable options.

Instead of calling Leonard’s bluff and hoping he’d eventually renege on his trade demand, the Spurs took what they could get on the open market, and the return was underwhelming. For a two-way dynamo that had recently finished in the Top 3 of the league’s Most Valuable Player voting, San Antonio received DeMar DeRozan, Jakob Poeltl and a single first-round draft pick.

That package wasn’t nearly substantial enough to keep the Spurs among the ranks of Western Conference title contenders, and it looked worse when Leonard led the Raptors to an NBA title the following June.

But the years since have been a little kinder to the Spurs’ end of the deal. The draft pick became Keldon Johnson, and subsequent trades of DeRozan and Poeltl led to pieces that have turned into DeAaron Fox and Kelly Olynyk and more draft selections and pick swaps that the Spurs have yet to make.

As for Leonard? He proved to be worth the investment for the Raptors, but not for the team that signed him away from Toronto. For all the millions and millions of dollars they’ve paid Leonard over the past six years – on and (allegedly) off the books – they still haven’t made the NBA Finals and made it past the second round of the playoffs only once.

Leonard’s constant health woes have been a big reason for that, and his unreliability now adds another problematic layer to the dilemma now facing Silver.

Los Angeles Clippers forward Kawhi Leonard (2) passes the ball as he drives past San Antonio Spurs forward Harrison Barnes (40) during the first half of their NBA game at the Frost Bank Center on Wednesday, Jan. 29, 2025 in San Antonio. With questions regarding possible salary cap circumvention surrounding Leonard and the Clippers, NBA commissioner Adam Silver faces a dilemma all too familiar to the Spurs. (Marvin Pfeiffer/San Antonio Express-News)

If the league’s investigation finds that the Clippers did try to circumvent the salary cap, the most severe form of punishment Silver is allowed to impose is voiding Leonard’s contract. But considering that Leonard played only 37 games last year and is still owed $100 million over the next two seasons, might that actually be doing the Clippers a favor?

Silver probably doesn’t want the mayhem associated with a free-agent frenzy for an All-NBA caliber player at the start of – or even during – a season. He probably doesn’t want the headache associated with suspending Steve Ballmer – one of the league’s most popular and influential owners – the same year the Clippers are set to host the All-Star Game. But if he looks the other way, and makes it appear Ballmer got away with violating a rule that is supposed to ensure the league’s sense of fairness, that might be even worse.

Again, there’s no good way out of this.

And if there’s a bright side?

Silver just hopes that, unlike the Spurs, he doesn’t have to wait seven years to find it.

Why LA Clippers forward Kawhi Leonard creates familiar dilemma for the NBA

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