When the Los Angeles Clippers acquired Kawhi Leonard in 2019, the organization believed it was making the move that would finally transform it from Los Angeles’ other basketball team into an NBA champion.

Seven years later, it’s difficult to imagine that gamble ending much worse.

The NBA has completed its nearly yearlong investigation into the Clippers’ dealings involving Leonard and found what the league described as a “pattern of misconduct and multiple significant rules violations” related to salary-cap circumvention. The punishment is staggering: five first-round draft picks forfeited, a $30 million fine and owner Steve Ballmer suspended from all team and league activities for one year. President of basketball operations Lawrence Frank was suspended without pay for six months, business operations president Gillian Zucker received a one-year suspension without pay, and the organization will be subjected to league compliance monitoring for five years.

Leonard was also found to have violated the league’s circumvention rules through the actions of his former business manager and uncle, Dennis Robertson. Yet compared to the punishment levied against the organization, Kawhi got off relatively easy. He wasn’t suspended and his contract wasn’t voided. Instead, Leonard was ordered to pay $700,000, while Robertson has been banned from doing business with NBA teams for five years.

There are a lot of different directions you can take this story, from what the NBA actually uncovered to whether the Clippers have grounds to challenge the findings. But one thing immediately jumped out to me when the punishment was announced.

Five first-round picks.

That isn’t a punishment you see very often in American professional sports. In fact, we really haven’t seen anything quite like it.

The NBA Dropped the Hammer

The investigation began after questions emerged about Leonard’s relationship with Aspiration Fund Adviser, a company that had also done business with the Clippers. The NBA ultimately found that Los Angeles had facilitated off-court income opportunities for Leonard involving four companies doing business with the franchise, induced companies to enter endorsement agreements by offering them team business, paid personal expenses for Leonard and his representatives, and failed to report improper requests for outside income made on Leonard’s behalf.

Commissioner Adam Silver didn’t exactly hide how seriously the league viewed those findings, saying he was “deeply disappointed” by the Clippers’ violations and organizational failures. The NBA also noted that Los Angeles was already a prior offender of its salary-cap circumvention rules, having been fined $250,000 in 2015 for improperly including an outside business opportunity in its pitch to DeAndre Jordan.

The Clippers vehemently disagree with the findings. They have accused the investigation of being biased and have promised to challenge the penalties, while Ballmer’s attorney called the process a “witch hunt” and the resulting punishment a “gross injustice.” The NBA and NBPA, however, announced that the penalties are final and binding, setting the stage for what could become another fascinating battle away from the basketball court.

Whatever you think of the investigation itself, though, the scale of the punishment is undeniable. The Clippers will lose their first-round selections in 2029, 2030, 2031, 2032 and 2033, including the unprotected 2029 first-rounder acquired from Indiana in the Ivica Zubac trade.

Five consecutive drafts without a natural first-round pick isn’t merely painful. It can fundamentally alter the trajectory of a franchise.

And that’s before you remember everything the Clippers had already given up to build this era in the first place.

The Real Cost of the Kawhi Era Is Almost Unbelievable

Kawhi Leonard technically signed with Los Angeles as a free agent in 2019, but everyone remembers the catch. Leonard wanted to play alongside another superstar, leading the Clippers to make the blockbuster trade with Oklahoma City for Paul George. The Thunder received a massive collection of draft capital in the deal along with a promising young guard named Shai Gilgeous-Alexander.

We know how that turned out.

Gilgeous-Alexander became one of the best players in basketball and the centerpiece of an Oklahoma City powerhouse, while the Clippers’ Kawhi-Paul George pairing never reached the NBA Finals. George eventually left Los Angeles, and Leonard’s time with the franchise is now effectively over after the Clippers agreed this summer to trade him back to Toronto, pending resolution of the investigation.

When you combine the original George trade with the punishment handed down by the NBA, the total cost associated with the Clippers’ pursuit of the Kawhi era becomes almost comical.

Shai Gilgeous-Alexander. Ten first-round draft picks. A $30 million fine. A one-year suspension for the owner.

And zero NBA Finals appearances.

The “10 first-round picks” figure comes from combining the five first-rounders Los Angeles surrendered in the George deal with the five the NBA has now ordered the Clippers to forfeit. Obviously, those weren’t all directly traded for Leonard, but they are all part of the enormous price Los Angeles has ultimately paid for the era that began with its pursuit of him.

If someone had told Clippers fans in July 2019 that this would be the final bill, nobody would have believed it.

Put This Punishment in Perspective

The reaction from reporters covering other sports really illustrates how extraordinary the NBA’s ruling is.

ESPN NFL insider Adam Schefter pointed out that no NFL franchise has ever been stripped of more than one first-round selection in a league disciplinary action. Think about the scandals the NFL has dealt with over the years and the punishments we’ve seen handed down. Even within that context, losing five first-round picks at once is almost unfathomable.

Then ESPN baseball insider Jeff Passan offered some MLB context. The Houston Astros were punished for the sign-stealing scandal surrounding their 2017 World Series championship by losing their first- and second-round selections in both the 2020 and 2021 drafts. That was considered an enormous organizational punishment at the time.

The Clippers just lost five first-rounders.

Comparisons across sports obviously aren’t perfect. An NBA first-round pick carries different value than an NFL or MLB selection because of roster sizes, developmental systems and the immediate impact one player can make. But that’s precisely why losing five of them is so devastating. NBA franchises have fewer opportunities to acquire premium young talent through the draft, and one first-round selection can completely alter the direction of an organization.

The league didn’t simply fine Steve Ballmer an amount that, considering his enormous wealth, he could absorb relatively easily. It attacked the Clippers where it could hurt them for years.

Kawhi Somehow Walked Away With the Lightest Bill

That’s also what makes Leonard’s punishment so fascinating.

The Clippers lose five first-round picks. Ballmer loses $30 million and is barred from participating in team or league activities for an entire year. Two high-ranking executives are suspended without pay. The franchise gets five years of compliance monitoring.

Kawhi?

$700,000.

Now, $700,000 is obviously an enormous amount of money to almost everyone reading this article. To Leonard, who has earned hundreds of millions of dollars during his NBA career, it’s considerably less imposing. More importantly, he isn’t losing games. His contract wasn’t voided. The league’s ruling clears the way for his previously agreed-upon trade back to Toronto to proceed, and Leonard has already said he’s focused on beginning his next chapter there.

I understand why the organization received the harshest punishment. Salary-cap rules ultimately have to be enforced against teams because teams are responsible for maintaining the integrity of the system. If franchises can simply find creative ways to funnel additional compensation toward players outside their contracts, the salary cap becomes meaningless.

Still, there’s something jarring about the imbalance.

The NBA’s investigation specifically concluded that Leonard, through Robertson, pressured the Clippers to help secure outside income opportunities, successfully obtained those opportunities and failed to reimburse certain personal expenses. Yet Leonard can pay his fine and continue his career while the Clippers could still be feeling the consequences of this scandal in 2033.

That’s quite a difference.

The Clippers Bet Everything on Kawhi—and Lost

It’s easy to forget just how understandable the original gamble looked in 2019.

Leonard had just led Toronto to an NBA championship and won his second Finals MVP. He was 28 years old and widely regarded as one of the best two-way players on the planet. Pairing him with Paul George gave the Clippers two elite wings and instantly transformed them into championship favorites.

If you’re Steve Ballmer and that’s the opportunity sitting in front of you, of course you go for it.

The problem wasn’t necessarily taking the swing. The problem is everything that happened afterward.

Injuries repeatedly disrupted the Leonard era. The Clippers blew a 3-1 series lead against Denver in the 2020 bubble. Leonard tore his ACL during the 2021 playoffs. George eventually left. Los Angeles never reached the NBA Finals, and the championship window that once looked wide open slowly disappeared.

Meanwhile, Gilgeous-Alexander became the player every franchise dreams of finding.

Then, just when it seemed like the Clippers could finally turn the page, the NBA handed them a punishment that will follow the franchise deep into the next decade.

It’s difficult to imagine a more brutal ending to an era that began with so much promise.

This Might Be the Most Expensive Failed Experiment in NBA History

The Clippers didn’t merely fail to win a championship with Kawhi Leonard. They leveraged an enormous portion of their future to acquire the co-star he wanted, watched the young player they surrendered become a superstar elsewhere, and now have another five first-round selections erased because of violations tied directly to their relationship with Leonard.

That is why I keep coming back to the final tally.

Shai Gilgeous-Alexander. Ten first-round picks. $30 million. Steve Ballmer suspended for a year. No NBA Finals appearances.

Kawhi Leonard, meanwhile, pays $700,000 and appears headed back to Toronto, the city where he experienced the greatest moment of his career.

There’s something almost poetic about that ending—unless, of course, you’re a Clippers fan.

Adam Schefter’s NFL comparison and Jeff Passan’s Astros comparison help illustrate just how severe this punishment really is. Other leagues have dealt with cheating scandals, salary-cap violations and organizational misconduct, but finding a comparable example of a franchise losing five first-round selections in one disciplinary action is nearly impossible.

The NBA wanted to send a message, and it sent one loud enough for every owner and front office in professional sports to hear: circumvent the salary cap at your own peril.

For the Clippers, however, that message comes years too late to change the decision that started all of this. They bet their future on Kawhi Leonard in 2019 because they believed he was the player who would finally deliver the franchise its first championship.

Seven years later, there is still no championship banner hanging in Intuit Dome.

Shai Gilgeous-Alexander is long gone. Paul George is gone. Kawhi is on his way out. Five more first-round picks have now disappeared, and Steve Ballmer will spend the next year away from the team he paid billions to own.

The Clippers went all-in on the Kawhi Leonard era. They didn’t just lose the bet—they may have received the most expensive losing ticket in NBA history.