Back in February of 2025, when Nico Harrison shipped Luka Dončić off to the Lakers for what amounted to little more than a hot beverage—presumably the same one he purchased for Rob Pelinka during negotiations—widely held opinion labeled it the absolute worst trade in the history of the NBA. The sole argument against that title was the fact that the Clippers’ acquisition of Kawhi Leonard back in the summer of 2019 wasn’t technically a trade. However, looking back at these moves strictly as business transactions, the signing of Leonard might have actually surpassed the Dončić disaster as the ultimate catastrophic move in league history. Though the Leonard era in Los Angeles appears to be on the verge of wrapping up, with his trade to Toronto finally moving forward after being delayed for two months, we should first examine this disappointing seven-year stretch. To begin with, the franchise shelled out almost $350 million to Leonard over the past seven seasons. For that massive investment, Los Angeles managed to secure just three playoff series victories, and Leonard was never healthy enough to participate in a postseason matchup past the conference semifinals. A torn ACL sidelined him for the entire 2021-22 campaign, and he managed to appear in just 37 contests during the 2024-2025 season. When he finally returned to the playoffs following his ligament recovery, he managed to stay on the court for only two games before a torn meniscus in 2023 sparked the first of three consecutive opening-round exits.
Based solely on those statistics, bringing Leonard on board was an absolute failure for the organization. Yet, that is merely the opening chapter of the financial wreckage. One must also calculate the massive and heavily documented acquisition cost of Paul George, who arrived as a mandatory package deal demanded by Leonard, meaning his price tag is directly tied to the overall expense of signing Kawhi. While that blockbusting trade for George was intended to secure a title, it actually did—just not for Los Angeles. Instead, the championship went to the 2025 Oklahoma City Thunder, the team that received five draft picks in the first round (including the one used to draft All-NBA talent Jalen Williams), a pair of pick swaps, and future consecutive MVP Shai Gilgeous-Alexander, all so the Clippers could combine Leonard and George on their roster.
Since any realistic evaluation of these maneuvers must treat the acquisitions of Leonard and George as one giant transaction, we must combine the nearly $200 million paid to George up to 2025 with Leonard’s $375 million on-court earnings (a crucial detail to specify). This leads us directly to Wednesday’s events, when the NBA concluded a nearly 12-month investigation by handing down severe punishments to the franchise for circumventing the salary cap in relation to Kawhi. The league’s official announcement detailed the team’s violations as follows:
- Proactively setting up external financial arrangements for Mr. Leonard with four corporate partners of the franchise: Aspiration Partners, Boingo Wireless, Daktronics, and Lockton Insurance
- Helping broker endorsement contracts between Mr. Leonard and these specific corporations
- Persuading these businesses to sign those deals by promising them team-related commercial opportunities
- Covering personal costs incurred by Mr. Leonard as well as his agents
- Neglecting to inform the league of illicit inquiries regarding external commercial opportunities initiated by Mr. Leonard’s business representative at the time, Dennis Robertson.
Stripped of its formal legal phrasing, this simply means the franchise arranged several effortless side gigs to funnel extra cash to Leonard beyond what the league’s collective bargaining rules permitted, resulting in exceptionally strict punishments.
Of course, those penalties are only painful for the franchise. Leonard, who reportedly pocketed more than $50 million in side revenue (separate from his $350 million in official team wages) through these backroom arrangements during his stint in Southern California, escaped with what amounts to a minor $700,000 fine. That is an incredibly favorable outcome for him. In contrast, the organization faced the full wrath of the league’s disciplinary powers. If the details uncovered by the investigation are indeed true, this severity was completely warranted. Allowing wealthy franchise owners to bypass league regulations and funnel illegal funds to players without consequences would create an uncontrollable precedent. The league needed to establish a firm boundary, and it did so by burying the franchise under a mountain of financial penalties and, far more damagingly, athletic deficits that will hinder their operations for many seasons to come.
To begin with, the organization was hit with a $30 million penalty. Regardless of an owner’s personal wealth, that is a massive sum of money. Furthermore, owner Steve Ballmer and the head of business operations, Gillian Zucker, both received one-year suspensions. Lawrence Frank, who oversees basketball operations, was handed a six-month suspension, with both Frank and Zucker forfeiting their salaries during their enforced time away.
Then comes the most devastating blow: the franchise must surrender five consecutive first-round draft selections spanning from 2029 through 2033. In today’s highly restrictive team-building environment, where draft assets are incredibly valuable for developing homegrown talent or putting together trade packages for established stars, this penalty is more than just a minor setback. It is a crippling blow comparable to the infamous ankle-breaking scene in the movie Misery. When you combine the assets surrendered for George (which was essentially the prerequisite price to secure Leonard’s signature) with Wednesday’s newly announced sanctions, the total damage is staggering: 10 first-round draft selections, future multi-time league MVP Shai Gilgeous-Alexander, two and a half years of total administrative suspensions, and an extra $30 million in penalties. All of these assets were squandered for the privilege of paying nearly $600 million in cumulative salaries to a Leonard and George tandem that failed to participate in, let alone win, a single conference finals game over a seven-year span.
Despite this outcome, it is worth remembering that nearly every franchise in basketball would have eagerly acquired Leonard back in 2019, especially with George coming off a year where he placed third in MVP voting. The decision to make that aggressive push was entirely rational at the time. While they certainly made a major mistake by engaging in the illicit side agreements that proved so costly, the pure sporting logic behind acquiring Leonard was completely defensible. It requires hindsight to label this transaction as one of the most disastrous in league history. In contrast, Nico Harrison and the Mavericks had full clarity regarding their situation and still chose to trade a peak-level Luka Dončić for a fading Anthony Davis while securing four fewer draft assets than Oklahoma City extracted from Los Angeles for George. This context is not intended to excuse Harrison or Dallas for orchestrating an incredibly short-sighted deal reminiscent of trading away Babe Ruth to finance a theatrical production.
Even so, Dallas ultimately ended up with Cooper Flagg. While they did not use the specific draft pick returned by the Lakers, keeping Dončić likely would have kept them out of the 2025 draft lottery altogether, where they beat the odds to secure the top overall selection with just a 1.8% probability. Deciding whether Dončić or Flagg is more valuable over the upcoming five seasons is a genuine point of contention. However, looking at the next decade, Flagg is almost certainly the preferred choice. Through pure fortune rather than strategic genius, the Mavericks came away from one of the most foolish moves in sports history looking completely pristine. On the other hand, the Clippers currently find themselves in a state of absolute ruin. Even when factoring in the pair of draft picks recovered from Toronto—with the Raptors likely relieved that the July agreement involving Leonard is apparently moving forward again—the team still suffers a net deficit of eight first-round picks as a direct result of the Kawhi acquisition.
There is no prize like Cooper Flagg to justify the organization’s massive missteps. The price tag for Kawhi grew increasingly painful year after year, culminating in the severe sanctions announced on Wednesday. While Steve Ballmer would likely never say so publicly, he must look back with deep regret on the decision to partner with Leonard, whose ultimate cost to the franchise has far exceeded any value he provided on the court.
