When Nico Harrison dumped Luka Dončić to the Lakers for not much more than the cup of coffee he presumably also bought for Rob Pelinka in February of 2025, it was considered by most to be the worst trade in NBA history. The only reason that might still be true is the Clippers didn't trade for Kawhi Leonard in the summer of 2019. But if we're talking straight transactions, with the benefit of hindsight, the Leonard acquisition may have just jumped the Dončić debacle in staking its claim among, and perhaps atop, the all-time disasters.
The Leonard era in L.A. is, presumably, ending any minute now, with the star player getting shipped to Toronto in a trade that was put on hold for two months. But, for now, let's look back at the failed seven-season run.
We can start start with the fact that the Clippers paid Leonard nearly $350 million over the last seven years. During that span, the Clippers won a total of three playoff series, and Leonard didn't play in a single postseason game past the second round. He missed the 2021-22 season entirely after tearing his ACL. He played in a whopping 37 games in the 2024-2025 season. In his first postseason back after the ACL tear, he lasted all of two games before tearing his meniscus in 2023 in the first of three straight first-round eliminations.
On those facts alone, the Leonard signing was a complete bust for the Clippers. But that's only the start of the accounting. There's also the extreme and well-chronicled cost of Paul George, who came as a package deal at the presumed behest of Leonard and thus has to be viewed as a function of Leonard's cost. That George trade was supposed to result in a championship, and it did. Only not for the Clippers, who sent five first-round picks (one of which became All-NBA player Jalen Williams), two swaps, and future back-to-back MVP Shai Gilgeous-Alexander to the 2025 champion Oklahoma City Thunder for the opportunity to pair Leonard and George.
Being that any honest accounting, as far as such a thing exists with the Clippers these days, of these deals has to look at Leonard and George as a largely single transaction, we're going to throw the almost $200 million the Clippers paid George through 2025 onto Leonard's $375 million basketball (important distinction) tab.
Which brings us to Wednesday, when the NBA, after a nearly year-long investigation, brought the hammer down on the Clippers for their Kawhi salary-cap circumvention shenanigans. In a press release, the NBA summarized the Clippers' infractions as follows:
- Affirmatively initiating off-court income opportunities between Mr. Leonard and four companies doing business with the team: Aspiration Partners, Boingo Wireless, Daktronics, and Lockton Insurance
- Facilitating endorsement agreements between these companies and Mr. Leonard
- Inducing the companies to enter into these agreements by offering them business from the team
- Paying personal expenses on behalf of Mr. Leonard and his representatives
- Failing to report improper solicitations for off-court income opportunities made on Mr. Leonard's behalf through his then-business manager, Dennis Robertson.
That's a lot of lawyer speak for the Clippers hooking Leonard up with a bunch of no-show side deals as a means of funneling him more money than they were legally allowed to pay him under the league's collective bargaining agreement, and suffice it to say, the penalties are harsh.
Well, they're harsh for the Clippers anyway. Leonard, who, according to reports, banked north of $50 million in extra income (on top of the $350 million in legitimate salary) for these secret-handshake setups during his time with the Clippers, got off with a reported $700,000 wrist-slap fine. Not a bad tradeoff.
The Clippers, on the other hand, got the book thrown at them. And assuming the league's investigative findings are accurate, they deserved it. You start letting rich owners route what amounts to illegal money in terms of NBA rules to players with impunity, and you'll never get the lid put back on. The league had to send a message, and it did exactly that by burying the Clippers under a mountain of financial and, more importantly, basketball debt that they'll be slowly crawling out from under for years.
For starters, the team was fined $30 million. I don't care how rich you are, that stings. In addition, Clippers owner Steve Ballmer and president of business operations Gillian Zucker were suspended for one year. Lawrence Frank, the Clippers' president of basketball operations, got six months leave, and neither Zucker nor Frank will be paid during their staycation.
And now for the biggie: The Clippers are forfeiting five straight first-round draft picks from 2029 to 2033. In the NBA's current roster-building landscape, which is as tight as it has ever been and puts an exponential premium on draft capital (either as a means of selecting future stars or trading for current ones), that's not just a gut shot. That's a hobbling that borders on Kathy Bates folding James Caan's ankles over the wooden block in Misery.
Counting the George cost (which, again, you have to look at as another handshake deal to get Leonard to sign in the first place) and the penalties handed down on Wednesday, we're talking about 10 first-round draft picks, two-time MVP and Finals MVP Shai Gilgeous-Alexander, two-and-a-half years of collective executive suspensions and $30 million more in fines that the Clippers essentially flushed down the toilet -- all for the right to fork over nearly $600 million in combined salary for a Leonard-George duo that, in seven years, didn't win or even play in a single conference finals game together.
Now, having said all that, it's important to note that every team in the league would've gladly traded for Leonard in 2019, and George was coming off a season in which he finished third in MVP voting. The Clippers were more than justified in taking that swing. They shouldn't have added in all the wink-wink deals that wound up costing them enormously, but from a basketball standpoint, it was a sound decision to sign Leonard.
It's only with the benefit of knowing how it all turned out that we can qualify this as one of the worst transactions in NBA history, whereas Harrison and the Mavericks had all the information right in front of them and still decided to trade a dead-in-his-prime Luka Dončić for a broken-down Anthony Davis and four fewer first-round picks than OKC swindled off the Clippers for George. None of this is meant to let Harrison or the Mavericks off the hook for truly one of the dumbest deals this side of selling Babe Ruth to fund a Broadway play.
Still, the Mavericks wound up with Cooper Flagg. Not with the pick they got back from the Lakers, but chances are if they didn't trade Dončić they wouldn't have fallen into the 2025 lottery, where they struck gold with a 1.8% No, 1 overall pick chance. I don't know if I would rather have Dončić or Flagg for the next five years. Reasonable minds can disagree on that. But it's an honest debate, and over the next 10 years it's almost certainly Flagg.
The Mavericks, albeit by none of their own doing, emerged from the bowels of one of the truly dumbest deals in history smelling like Chanel No. 5. The Clippers, meanwhile, are reeking like a rotting organizational corpse right about now. Even if you factor in the two first-round picks they got back from the Raptors -- who are, by the way, breathing a massive sigh of relief as the Leonard deal they struck in July is now presumably back on -- that's still an eight-draft-pick net loss for the Clips on the Kawhi ledger.
There's no Cooper Flagg to show for their screwup. They paid a cost for Kawhi that became more and more punitive with every passing year, with the biggest penalties being saved for Wednesday. Ballmer would never admit it, but he has to be regretting the day he went into business with Leonard, who has, as of Wednesday, officially wound up costing the Clippers way more than he was ever worth.
