The Kawhi Leonard Scandal Raises the Alarm: Are Salary Caps Fair, or Fiction?

7 hours ago 11

Rommie Analytics

Hello and welcome to another edition of Free Agent. Don't call, don't text, my Lions were trash on Sunday. The world is dark and cold until we win again. Our playoff odds are in the tank and I'm now worried about a game against the Bears, of all things.

In short, I hope your Sunday was better than mine (unless you're a Packers fan, in which case I hope your kitchen perpetually smells like moldy cheese). But we're not here to talk about the NFL; we've got to talk about an absolute bombshell involving Kawhi Leonard and salary cap circumvention. Speaking of which, do we even need salary caps? Then we'll discuss Formula 1 changes and Mario Kart (separate topics, unfortunately).

Locker Room Links

Sen. Tammy Baldwin (D–Wisc.) and Rep. Tony Wied (R–Wisc.) introduced the Go Pack Go Act because they think they'd do a better job of analyzing media markets than the NFL, and I'm in no mood for that. Spending $7 million in taxpayer money on LIV Golf is not going to pay for itself, Louisiana. Perhaps you saw the video of "Phillies Karen" over the weekend. She was clearly in the wrong—no one is entitled to the ball in a scrum like that. But the people trying to dox her and ruin her life are in the wrong, too. As the dad in the video kindly said on Fox News, "I'd love to get the ball to give back to my son. But I don't want anything bad to happen to her." "Chinese tycoons turned pigeon racing into one of the world's most lucrative sports." As President Donald Trump went to the U.S. Open, the tournament told broadcasters not to show any protestors on TV. "Tariffs on Mailed Goods Hit U.S. Sports Fans—If They Get Delivered" Elsewhere in Reason, by Free Agent's hardworking editor Jeff Luse: "Trump Once Called Biden's $1.2 Trillion Infrastructure Bill 'Terrible.' Now He's Pretending He Signed It." Good news for taxpayers after Army paid $250,000 to lose to Tarleton State.

Kansas State paid Army $1.175M to play in Manhattan.

The Black Knights just upset the Wildcats 24-21. pic.twitter.com/flK6Yw0kFX

— Front Office Sports (@FOS) September 7, 2025

All Kawhi-et On the Clippers Cap

If you don't have two hours and 40 minutes to listen to Pablo Torre Finds Out, I've got you covered with everything you need to know about the Kawhi Leonard scandal. (For the record, as a Detroit Pistons fan, I don't have especially strong feelings about the Clippers other than I like their new boat logo—although in writing this, I learned Clippers owner Steve Ballmer grew up in Michigan.)

The NBA has a salary cap. Teams are not allowed to spend over the salary cap (it's a complicated "soft cap" with luxury taxes, aprons, and exceptions, but that's not important here). The rules are strict enough that teams can't give away special perks to their players (Torre's examples of banned perks include big things like private jets but also smaller things like special courtside seats for family).

It sure seems a lot like Ballmer paid team superstar Leonard roughly $48 million off the books to skirt the salary cap.

The scandal involves a company named Aspiration. It's a weird company that's technically kind of a bank, but also a broker for planting trees when you want to pay extra for something because you feel bad about your environmental impact. If that doesn't sound very promising to you, you're smarter than a lot of venture capitalists: It filed for Chapter 11 bankruptcy in March.

That bankruptcy is how everything came out. One of their biggest creditors is a company named KL2 Aspire LLC—Leonard's initials and jersey number. He had a $48 million deal with Aspire ($28 million in cash and $20 million in company stock), several times more than all their other celebrity endorsements combined.

But you wouldn't know it, because Leonard never did a single thing to promote Aspiration.

This wasn't just something Ballmer allegedly arranged between Leonard and Aspiration. Ballmer and Aspiration were tightly connected. Aspiration was a major sponsor of the Clippers, in the arena and on a jersey patch. Ballmer, one of the richest men in the country, had hundreds of millions invested in Aspiration. One of those investments was worth $50 million—made right around the same time Leonard signed his $48 million deal.

For what it's worth, billionaire Mark Cuban, still a partial owner of the Dallas Mavericks, doesn't believe Ballmer did this on purpose and puts the blame on Leonard's main agent and negotiator, "Uncle Dennis." I found his arguments pretty confusing and unconvincing. He had all kinds of reasons Ballmer wouldn't do this, but no explanation for why Aspiration would make a no-show endorsement deal or why Torre's seven sources at Aspiration would lie about being told by higher-ups that the Leonard endorsement deal was created to circumvent the NBA salary cap.

Those higher-ups, by the way, have political connections worth pointing out. The two co-founders of Aspiration are Andrei Cherny and Joe Sanberg. Cherny was a Democratic speechwriter for President Bill Clinton and for John Kerry's 2004 presidential campaign, and has several failed campaigns for public office. Sanberg considered a presidential run in 2020 but decided against it—then he was arrested in March 2025, and eventually pled guilty to defrauding people of $248 million.

There's enough plausible deniability that a jury might not convict Ballmer and Leonard if cap circumvention was illegal. The NBA doesn't have to have the same standards as a court, though, and the evidence is damning. We have an owner who tried to circumvent the salary cap in 2015, a player's agent who tried to do it in 2019, a no-show endorsement deal for that player whose total value was nearly equal to that owner's investment in that company around the same time, and seven sources saying "This was salary cap circumvention!"

For all that, I'd bring down the hammer if I were the NBA.

Capped Out

All that raises two questions: How often are salary caps getting bypassed, and should leagues even have them?

After the Leonard scandal came out, people raised questions about Jalen Brunson's cheap contract with the New York Knicks. Same with Dirk Nowitzki's cheap deal with the Mavericks in 2014. In the NFL, I recall some rumblings about Matt Stafford when he played for the Lions (owned by the Ford family) and had endorsement deals with Ford.

Maybe salary caps are too hard to enforce? Is the difference between a fair endorsement deal and a cap circumvention deal too inscrutable? As the NCAA has shown, it's really hard to keep people from taking outside deals, even under-the-table ones.

What leagues are trying to avoid is rich owners, or teams in rich markets, dominating the less-rich owners in smaller markets. If the Cowboys won the Super Bowl every year, I'd probably just stop watching the NFL. It's not a good libertarian way to govern sports, but it's good business. MLB can manage without a salary cap because the game, and the playoffs, are random enough to keep the Yankees and Dodgers from dominating every year. Then again, European soccer leagues have no salary cap and the same few teams tend to win most domestic league championships (without the benefit of playoffs to introduce some chaos).

Those soccer leagues also have open markets, though—or as you might call it, promotion and relegation on a ladder of top leagues and lower leagues. It keeps one team from dominating a big market like, say, London, which is currently home to seven of the Premier League's 20 teams. What if the Yankees and Mets had two or three more teams in New York to compete with them for fans and money?

Salary caps have pros and cons. Regardless, the Leonard scandal shows the difficulty of enforcement. And remember, if players weren't unionized, salary caps would be illegal anyway, or at least legally questionable.

What do you think? Is it better for leagues to have salary caps or not? And if it seems like teams have broken the cap, how would you punish them? Send me an email at [email protected] and let me know what you think.

Tinker Time in F1?

Does Formula 1 need major changes? F1 CEO and President Stefano Domenicali thinks so, and he's overseen the series reaching new heights in his five-year tenure, so he's got credibility. 

The supposed problem, according to Domenicali, is that younger audiences are watching highlights instead of races. Minor changes have been floated, including more sprint races and awarding points for practice sessions (which wouldn't really be practice then, would it?), but the most radical idea is shortening the length of races. The problem isn't really the length of races, though, it's the lack of action. McLaren drivers speed away from the rest of the field and dominate this year. So it goes.

But all this talk is premature to me. Next season will bring some radical changes already.

The drag reduction system (DRS) is out, meaning no more DRS zones where most of the passing happens. A new push-to-pass system replaces it—that will hopefully mean more passing, aided by cars that are slightly smaller than current ones. The new season will also feature an additional team (with fan favorite drivers Sergio Perez and Valtteri Bottas). Two extra cars in races means more opportunities for passing, drama, and incidents. Expect safety cars and red flags to be more likely—they can always lead to more chaos.

There's enough change coming next year in F1. Wait and see how that plays out before even thinking about more change.

Look Out for Bananas

Technically Mario Kart World is a motorsports video game, right? That makes it fair game for this newsletter. As someone who has played most entries in the Mario Kart franchise since the Nintendo 64 version, the new game for Nintendo's Switch 2 is great.

There are over 50 characters, many with alternate costumes you can unlock (Aristocrat Boo is among my favorites). But the real genius is in the game's open-world design—not in the open-world playmode (which is fine), but in the way you can race from one course to another. So it's not just 30 courses spread across eight grands prix, it's hundreds of combinations connecting various courses to another. (Boo Cinema and Acorn Heights are favorites of my wife and me.)

Unfortunately, the famous blue shells that knock out whoever is in first place are still in the game. Blue shells are socialism.

Replay of the Week

As we all know, the rest of this game was boring and uneventful.

ARE YOU KIDDING @DeAndreHopkins????

TOUCHDOWN RAVENS!!!! FIRST CATCH AS A RAVEN!!!! pic.twitter.com/GahQ5EKVqV

— Baltimore Ravens (@Ravens) September 8, 2025

That's all for this week. Enjoy watching the real game of the week, Rhode Island F.C. vs. Sacramento Republic F.C. in the can't-miss USL Jägermeister Cup semifinals.

The post The Kawhi Leonard Scandal Raises the Alarm: Are Salary Caps Fair, or Fiction? appeared first on Reason.com.

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