Monday Daily Duncs (9/8/25)

Aspiration

Aspiration – the company linked to the Kawhi Leonard scandal – apparently had a history of paying celebrities for no-work marketing deals on the secret condition the celebrities hired Aspiration, allowing the company to artificially inflate its revenue numbers, Matt Levine of Bloomberg covers.

The way this might have worked: Aspiration and/or its founder secretly pledged to give Leonard $48 million. In a separate, but actually connected contract, Leonard agreed to buy [amount less than $48 million] in services from Aspiration. Leonard could pocket the difference. Aspiration could claim higher revenue, using the inflated figure to court new investors.

That strikes me as a plausible explanation – importantly, one that would absolve Steve Ballmer and the Clippers.

If that's the defense and I were the NBA, I'd demand Leonard show proof he agreed to pay Aspiration/paid Aspiration (or give some other explanation for his lucrative no-show endorsement deals). The catch: Leonard/whomever set up the deals for him could face legal liability.

Leonard could be pressed into some difficult choices ahead.

Collective Bargaining Agreement

The Clippers could claim Kawhi Leonard entered into the just-described scheme. Leonard could refuse to corroborate that.

In many situations, that wouldn't be enough evidence to find wrongdoing.

But the Collective Bargaining Agreement specifically says salary-cap-circumvention can be proven by "circumstantial evidence."

Steve Ballmer – whose Clippers were previously fined for attempting to circumvent the salary cap with DeAndre Jordan – paid Aspiration $50 million. Aspiration agreed to pay Leonard $48 million. That's textbook circumstantial evidence.

It'd look even stronger if Leonard doesn't provide another explanation.

Is that enough circumstantial evidence? Well, that's up to Adam Silver. But I'd say it'd be a gray area where he could punish the Clippers if he wants to or not if he doesn't.

Collective Bargaining Agreement

One other part of the Collective Bargaining Agreement I found interesting, on teams being prohibited from agreeing with a sponsor to pay a player for basketball services ("even if such compensation is ostensibly designated as being for non-basketball services"):

"Such an agreement with a sponsor or business partner or third party may be inferred where: (i) such compensation from the sponsor or business partner or third party is substantially in excess of the fair market value of any services to be rendered by the player for such sponsor or business partner or third party; and (ii) the Compensation in the Player Contract between the player and the Team is substantially below the fair market value of such Contract."

It's not hard to argue Kawhi Leonard getting $48 million for a no-show job is "substantially in excess of the fair market value." As Pablo Torre reported, Leonardo DiCaprio got a fraction of that and actually had to do endorsement work for Aspiration.

Whether Leonard's Clippers contract is "substantially below the fair market value" is much trickier. He signed for the max in 2019 and 2021 (and slightly less than the max in 2024).* But the best max players – like Leonard in 2019, when had multiple max suitors trying to differentiate themselves – are worth much more than the max. The NBA doesn't have a fair market. Can the NBA argue that, though? Did Leonard qualify as one of the best max players in 2021, when he had a torn ACL?

*If the Clippers were secretly funneling money to Leonard, I'm unconvinced the timing of his Aspiration deal matters much. This could have been a continuation of an under-the-table plan hatched in 2019 and involved multiple payment methods. To be clear, I'm not alleging that. I'm just not assuming it isn't the case.

L.A. Clippers

"A Clippers source" compared tampering to a speeding ticket and salary-cap circumvention to a murder charge, according to Dave McMenamin of ESPN.

That's quite the comparison to make, even anonymously!

From Steve Ballmer down, the Clippers are acting as if they won't be found to have done anything wrong… which will only make them look worse if they get busted. They could try to tamp down the stakes. They are doing the opposite.

Which maybe indicates innocence… or hubris.

Uncle Dennis

"Uncle Dennis" (Kawhi Leonard's representative and uncle, Dennis Robertson) asked the Raptors for an ownership stake of the Toronto Maple Leafs in 2019, according to Bruce Arthur of the Toronto Star. The Raptors and Maple Leafs share ownership, so that would have been a clear CBA violation.

There were obviously some sour grapes in Toronto about Leonard leaving. But Robertson also reportedly sought illegal inducements from the Lakers.

Though the NBA investigated and found no wrongdoing by the Clippers at the time, doubts still fester.

Whatever actually happened with Leonard and Aspiration, it's remarkable the player most-linked to circumvention is the one caught in this scandal.

Trees

Fun article (at least I found it fun) by Louis Keene of Unstatable in 2020 on the Clippers' new arena and how the organization would get tied into a tree-planting company like Aspiration (which isn't specifically mentioned in the article).

Dwight Howard, Carmelo Anthony

Kevin Pelton of ESPN puts into perspective the careers and Hall of Fame inductions of Dwight Howard and Carmelo Anthony, who comprise a small but mighty NBA-player Hall class.

Hall of Fame

Zach Kram of ESPN forecasts which current NBA players will eventually make the Hall of Fame. I'm most intrigued by the "Circle back in a few years" group, which is comprised of:

  • Tyrese Haliburton

  • Jalen Williams

  • Chet Holmgren

  • Evan Mobley

  • Cade Cunningham

  • Paolo Banchero

  • Zion Williamson

  • Ja Morant

  • Trae Young

  • LaMelo Ball

  • Scottie Barnes

  • Alperen Sengun

  • Tyrese Maxey

  • Stephon Castle

  • Amen Thompson

  • Cooper Flagg

I'd like to know: If you took a similar (though perhaps slightly more tightly cropped) snapshot, say, 15 years ago, what percentage of the group would be Hall-bound?

Is Evan Mobley, for example, a likely future Hall of Famer? Obviously, he's not close yet. But he also isn't close to finished. I'd love to know more about where the line is for giving a promising young player over 50% Hall of Fame odds.

-Dan Feldman