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Mike Vanov
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Dave Dufour
I wish I would stop overthinking.
Mike Vanov
Take a breath.
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Mike Vanov
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Dave Dufour
Welcome back to the NBA Daily. I'm Dave Dufour here with Mike Vorkanoff who covers the intersection of sport and business, in particular basketball. And you guys know we're talking about Kawhi Leonard and the LA Clippers and their owner, Steve Ballmer. Mike, how's the last couple weeks been for you, man?
Mike Vanov
Sure has been a very quiet NBA summer, hasn't it? Like we're all just kind of relaxing, chilling here, enjoying our Labor Day weekends.
Dave Dufour
Yeah, I mean, I was trying to just I wanted to watch Eurobasket and just like as a fan and you know, I've been able to do that, I'm not going to lie. But this, this Kawhi Clipper story is distracted and just kind of taking up a lot of my attention. You put out a bombshell to a certain degree on Friday when you revealed that the Clippers owner Steve Ballmer invested an additional $10 million in aspiration, the company that was sponsoring Kawhi Leonard. And for those of you who aren't up on the story, Pablo Torre, from Pablo Torre finds out, broke the the news a couple weeks ago that there was, let's just say, an interesting relationship between Kawhi Leonard and this company, Aspiration, where he had a sponsorship deal that essentially required nothing of him. And there were links to Clippers owner Steve Ballmer. Mike, you've been on this story essentially since it broke, working behind the scenes. I mean, what does this look like to you?
Mike Vanov
Well, what it looks like is a very interesting, complicated relationship between aspiration, which is for everyone who had not heard of aspiration before this, and I think that'll probably go for like 99.9% of us. Kind of like a carbon offsetting tech firm bank out of California that signed a contract with Kawhi Leonard for four years, $20 million for a sponsorship deal back in April 2022, only a few months after it inked a very large 300 million plus sponsorship deal with the Clippers. As for the Kawhi Leonard part of was an endorsement deal where he didn't really have to do any endorsing. There's some stuff laid out in the contract that what he would have to do, he ultimately did not do any part of it. You know, there is some confusion and consternation within the company about why they signed him as an endorser, considering Kawhi Leonard has never been kind of the eco friendly sort publicly at least. He's never, he doesn't have much of a social media presence at all, which is also valuable to the company at that time. And the thing that also makes this very interesting on top of all of it is that Steve Ballmer put $50 million into the company as an investor in December of 20. Pablo Torre, you know, first raised this whole web of connections on his podcast. And then I reported Friday that Steve Ballmer invested another $10 million in March of 2023 into aspiration. The timing is, of course, interesting. It was during a fundraising round when the company was really struggling. They couldn't raise as much as they wanted. Most of the funds were raised by two previous investors. Its co founder, who has since agreed to plead guilty to federal charges of fraud, and a board member who has also pled guilty to federal fraud charges. And most of the new money came from Steve Ballmer and 2 million from the Clipper's vice chairman and his good friend Dennis Wong. And Pablo Tori found out, finds out, found out. A few days later, the company, in the middle of financial distress, sent $1.75 million to Kawhi Leonard after Dennis Wong's investment. And, you know, the company was firing people. It was losing. It was, it was burning through money at a quick pace. It was really, you know, desperate for cash. And Steve Ballmer put money into that, you know, ten more million dollars into the company at that time, which is surely going to raise more questions about the level of his relationship with aspiration and what's going on there between him and Kawhi Leonard and that company?
Dave Dufour
Well, I mean, and in your article, you point out that Joe Sandberg, who is one of the guys that you mentioned, he. He gave 20 million of his own stock to Kawhi, you know, as part of this deal, or promised it, I guess.
Mike Vanov
Yeah, he. He insisted on giving $20 million in stock in shares of aspiration to Kawhi Leonard at the same time the deal was completed. Again, which raises more questions. You know, he pledged a lot of his equity in the company to take out personal loans. So why would he give away $20 million to Kawhi Leonard at that same time? The math on that, obviously, by circumstantial evidence adds up, which is Kawhi received $20 million in endorsement deal, $20 million in stock, and a Steve Ballmer put in $50 million. Right. And so that obviously has a lot of, you know, interesting questions around it.
Dave Dufour
So where are we now?
Mike Vanov
You know, we're.
Dave Dufour
We're a few weeks in. The league is investigating. We had the board of governors meeting last week. You know, Adam Silver's first chance to really address this stuff. You know, what's like the feeling around the league.
Mike Vanov
Yeah, look, the NBA has its investigation going, right? It's investigating whether the Clippers circumvented the NBA salary cap, which is an NBA terms like capital offense. That's the rule you don't break. You get fined a lot of millions of dollars. The player gets fined. The league can take away draft picks. It can void the contract even. It can suspend executives and owners from being near or part of basketball operations. So that is serious stuff, right. Aside from banning you from the league, that's probably the most serious punishment that Adam Silver can hand down. So the league is investigating it. They've set kind of, you know, the rules for the road, which I thought was interesting. Adam Silver, in his press conference last week said that they will be looking for proof. Right. Not circumstantial evidence. Not, hey, this looks like the mere appearance of impropriety. I think something like that was his words. They want the impropriety. They want it before they rule on it. And they said the burden of proof is on the NBA here. So that kind of lays down what they're looking for. Right. To me, that says that's the threshold we're looking for, and we need to see if the Clippers went past it, you know, and so it's gonna be interesting to see where the NBA goes. I think the pressure publicly is on them to do something right. Pablo Torres reporting. Our reporting like to this point has raised a lot of questions about what the Clippers did and why Kawhi Leonard got paid a lot of money and you know, according to my sources, more money than, you know, other celebrity endorsers receive from that company. Right. So we'll see what the NBA finds. It's kind of interesting. I think an interesting wrinkle in this is that it doesn't have subpoena power on people that are outside the NBA's purview. It can compel Kawhi Leonard to be a part of the investigation and I'm sure he'll be a great interview once you get him under the dangling headlamp there. That I'm sure is somewhere in the deep recesses of the NBA office and Steve Ballmer will be a part of it and other Clippers people and Kawhi's registered agent with the nbpa. But I don't think Uncle Dennis is compelled to talk to the NBA by my understanding of the rules. The people from aspirations certainly aren't compare compelled to talk to the NBA. And so what the NBA can find out who's willing to talk to them is all going to be part of like I mean frankly the circus of this investigation, right? It's not who just who did what when. It's also who can we talk to to find out about the, you know, who, what, when and where and why?
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Dave Dufour
It is. Neil, say it is a wild story that it just, I mean there's now multiple Dennis's. I mean it's, it really is. It's gotten convoluted. But you know, people have been comparing it to the Minnesota Timberwolves and the sort of, you know, behind the scenes deal they had with Joe Smith. And now you don't you think that that was worse? Right. Like we were talking before the show, I just, I'll lay it out there. You feel as if that one was more egregious. Can you lay out like the particulars of that one? Because I do think a lot of people have made the comparison. But there's not been much talk about what actually happened with Joe Smith and the Wolves.
Mike Vanov
Yeah, the Joe Smith thing from, I think it was 1999 or 2000, the NBA found again and this all stems from. They would have gotten away with it if there wasn't that pesky lawsuit edition of NBA rule breaking. They found that the Timberwolves and owner Glenn Taylor signed three successive one year deals with Joe Smith so they could retain his bird rights. They paid him less than he was worth every time. And at the end of it had an agreed upon $86 million contract. I think six years, $86 million. That's something you can't do. You can't, you can't just agree to like four contracts ahead of time below the market value so you can squeeze some people in so then you can pay more at the end of the road and you know, go above your salary cap to be able to pay them that. And so they find them. I think it was five first round.
Dave Dufour
Picks, but they actually found a smoking gun there. Right. Like they did the document. Right?
Mike Vanov
Yes. Yeah. I don't know if it was literally or proverbially sitting in Glenn Taylor's desk somewhere in a folder, but they had you know, the four. They had four contracts, right? Like basically the three one year deals and the $86 million contract. And they had the smoking gun. They had the act of impropriety, not just the mere appearance of impropriety. And they took away five first round picks. I think they got lower to three. They find them the Timberwolves money. They, I think, suspended Glenn Taylor for a year. They voided the contract. So they came down with the full weight of all the punishment that the NBA could dole out.
Dave Dufour
But you're saying that in, in this instance, without a smoking gun, like you wouldn't expect anywhere close to that sort of punishment, if there's any.
Mike Vanov
I think right now there's not yet a smoking gun. There's a lot of stuff that doesn't look good for the Clippers. And I think the more we learn, every time we learn something more, it looks worse and worse for the Clippers. And look, by the time you listen to this podcast, maybe there's more stuff that could be something new ruling anything out.
Dave Dufour
There's a third Dennis, maybe, you know.
Mike Vanov
Yeah, yeah. But I think at this point we certainly have, I think we have the, we have circumstantial evidence that doesn't look good for the Clippers, but I don't think we have anything yet to definitively prove cap circumvention. It seems like that the NBA is looking for. Right. How much of this takes something in the middle?
Dave Dufour
Well, how much of this is. Is just us finding out how so much of the sausage gets made. You know, I mean, you know, one of the things that came out, Nate Jones, who is a sports agent, he works with players, he actually mentioned that the, the sponsorship deals with the, the, the team sponsor, in the language of the contracts, if you leave the team, that the sponsorship deal ends. That's not abnormal. And honestly, it makes sense. You know, like part of the deal is, hey, you're with the team. That's why we're interested in having you as, as an endorser. But you know, this is a, the no show aspect of this is the, and, and the money is the weird part. But if, if Kawhi had been showing up to do stuff, do you think we even have this conversation right now? Like, I mean, it, it's how much of that, this behind the scenes stuff is abnormal?
Mike Vanov
Well, yeah, I mean, there's a lot of stuff to kind of like pull apart in this. Right? The no show aspect matters. Now. Was it that he didn't perform on the contract because they didn't want him to, you know, which is an explanation I've heard, which is, you know, he doesn't have a social media presence, so what's he going to tweet about our company? Right. He's not really aligned with our brand, so what's he going to do for our company? And maybe he just didn't want to do anything, period. And if he didn't, then why didn't you void the contract? Right? Was it that we just decided not to do anything with it because this is something one of our board members handed down to us, and we're like, we don't know how to make the best of it, or is this something where it was created in a way for him to never have to do anything on it? That part matters, right? That intent matters. Obviously, the origin of the contract matters too, right? Was this legitimately, hey, we're brand sponsors, we're founding sponsors, I think was the technical term for the Clippers and the new Intuit Dome that they built. And we want to be aligned and maximize our partnership and to get something in place with Kawhi, who's their star player. Right? Like that could be a reasonable explanation. Or is this just like, hey, we just want to help them and, you know, we want to help out Steve Ballmer and the Clippers, get Kawhi Leonard and help them circumvent the cap. There's a lot we don't know. And intent will probably matter to this investigation. And the other part we don't know is the person at the center of this whole thing from aspiration that, God, we're talking so much about the company. This is like the best marketing it's ever gotten, is that the board member who helped drive this deal is, you know, dealing with a federal case at this moment. How will the NBA be able to reach him? What was he thinking? You know, what did he intend that contract to mean and how did he intend for it to play out? And what were his conversations with Steve Ballmer during all this when he wooed the Clippers of sponsors and him as an investor, like, there's so much we don't know at this point. For me to definitively say, you know, what this all. Look what this all will be.
Dave Dufour
Or maybe I'd be shocked if there was any sort of smoking gun to the likes of which Glenn Taylor and Joe Smith had, where there's a contract that says, hey, wink, wink. This is just so that you sign with the Clipper. This is too complicated of a scheme. If let's you know, and I'm, I'm erring on the side of they're guilty of this. So if they are, it's too complicated of a scheme for something like that to exist. And if they're not, then it wouldn't exist in the first place. So I just don't think we're going to get the satisfaction of a black and white cut and dry smoking gun. I mean, you probably feel the same way. You've seen more of this stuff than I have. I mean, I'm sure your eyes are.
Mike Vanov
Red from it at this point. I'm operating and I know this is like maybe not the sexiest opinion of like, I don't know what I don't know. Right. Because I think there's a lot to not know here. And you know, the more that I think we all find out about this company that I think the more red flags that are raised. Right. And I, you know, are there more investments? How are the next time is paid? We, you know, Kawhi Leonard signed a $28 million contract. He's a creditor for $7 million. Was he paid the full $21 million? If he was, how did he get paid? And why did he get paid at a time when the company ultimately was in such financial trouble it filed for bankruptcy this past spring? Right. Like all those are relevant questions. But I think as of right now, as I said, the circumstantial evidence is not pointing the Clipper's favor. Steve Ballmer has denied all this. Right. And he said that they have proof. And they said that they've gone through, you know, talking to the DOJ in a, I guess, you know, the founder of the co. Founder of aspiration federal charges. He's got SEC charges against them. I'm sure that someone from the Clippers maybe was contacted by the DOJ to see what they knew. So they said they have proof of, you know, their innocence. So what, what do they have? What is the proof? Right. Like it, you know, if they have this definitive proof, maybe they can come out and they should probably put it out.
Dave Dufour
What about the pattern of behavior though with the Clippers? You know, there was the 2015 DeAndre Jordan stuff. I mean, just this. Over the weekend, a podcast clip resurfaced from Patrick Beverly talking about signing a below market deal in exchange for 94 basketball courts. And he's still, he's upset about the other 92 that didn't get built. I mean, like, you know, I don't know. It certainly seems like the Clippers are doing a Lot of walking like a duck here.
Mike Vanov
Yeah. I mean, I think the biggest scandals are the ones that lean into our presumed assumptions. Right, right. And, and so, you know, they got fined in 2015 for making a presentation of a sponsorship to DeAndre Jordan during their free agency pitch to him, which they can't do. Right. The NBA said, and obviously when Uncle Dennis, when we first heard his name back in 2019, the league investigated other cap circumvention charges against him and the Clippers and Bruce Arthur for the Toronto Star had this great report about, hey, Uncle Dennis seemed to ask for these exact things from the Toronto Raptors six years ago. Right. Like, so all of this, to your point, seems to be following a pattern of some sort, either by one side or the other, or at least we have like prior guilty occasions. And so it's interesting, we also have to figure out the cap was, you know, if there was cap circumvention, for what purposes was it? The 2019 contract, the 2021 contract, the 2024 contract? Right. Like, there's three contracts that Quiet Leonard signed here. And the 2024 obviously had the biggest potential haircut from a max deal. So again, like, if the NBA is taking a, a, a very strong approach to needing proof of this, I'm curious, what will be enough for them?
Dave Dufour
What about with fans? You know, I, I, I think about this quite a bit. You know, the, the integrity of the league sort of thing. It's, it's why I get into officiating and, and the inconsistencies there. But this is off the court officiating. This is literally the team building that they've designed the sport around. What if no punishment comes from this? You know, and again, it looks like something happened here. We don't have a smoking gun, but it certainly looks like something happened. So if, if they do nothing, do you feel like the fallout with the fans is worth that? Not, you know, not that fans need to dictate this or their feelings, but I do think it's something that needs to be taken into consideration.
Mike Vanov
Yeah, absolutely. Look, this is a business with, you know, that's not based solely on sales. Right. It's based on public sentiment. It's based on public interest. Right. Like the NBA is a sport and it's an entertainment vehicle. Right. It is both. It has to walk the line. So the public relations of that matter. Because you don't want to disenfranchise your customers. Right. Like you don't want to disenfranchise the people who make you what you are as a league. I can't. Look, I can't claim to speak for fans. Right. I am not one. Sure. I don't root for a team, but, I mean, it's got to be, I would assume, you know, pretty deflating if, like, if you feel like a team is out there not playing by the rules and maybe you think your team is not or is not capable of doing that. To me, I don't know if it's much different or not much different, but I don't know if this kind of, like, goes back to when there was cheating back in college sports and paying players under the table. Right. And that was obviously a punishment created by the ncaa, but one that gained relevance because every time somebody was caught doing it, they got punished for it. And so here it's a similar thing. Right? Like, it's a thing because the NBA is a sour cap and you can't circumvent it. But do we assume or do fans assume that it happens frequently? I. I don't know. And if so, do they then not expect that large of a punishment anyway? Because if the assumption is everyone's doing it or a lot of people are doing it, then why punish in the first place? Right?
Dave Dufour
Yeah. I mean, it feels like if. If they didn't cheat doing this, they at least created a nice blueprint for some team that wants to give it a shot because it's, again, it's very complicated. Mike Vanov, go and read him at the Athletic. I'm positive you've got more coming this week and in the future on this story. Also, by the way, I got to ask you real quick before we go, Adam S. Adam Silver was talking about fans who couldn't afford streaming services to watch the NBA, and he called the NBA a highlight sport. Now, I feel like that probably struck a nerve with you, did it?
Mike Vanov
It's so weird, right? Like, the NBA is a highlight sport.
Dave Dufour
It is.
Mike Vanov
You probably shouldn't say it's a highlight sport because there's a whole game and you want people to care about the whole game. Right. Like, all 48 minutes should matter. Not just like the two and a half on YouTube or Twitter, but it might be one of those things where it's. You're just telling the truth. It's just too close. It's too close to the truth. It's too close to mattering. I. I feel like a lot of people consume the NBA's highlights, don't you?
Dave Dufour
Yeah. I mean, it. It definitely has gotten that way. I mean, it's hard. It's hard enough to watch a game tell me which channel it's on.
Mike Vanov
Mike well, yeah, that and it's like what channel is it on? Am I going to pay more? Like, you know, it's going to make me watch more highlights If I have to pay for Peacock now when I didn't have to. If I have to pay for ESPN plus when I didn't have to. If I have to pay for Amazon when I didn't have to. Right. Like all these things, every new friction point between my wallet and the NBA is going to lead me way more towards watching the highlights the morning after.
Dave Dufour
That's right. Again, Mike covers so much with the sport of basketball and especially the stuff where the business intersects and that's why I had to get your take on the streaming and the highlights.
Mike Vanov
I care about that stuff.
Dave Dufour
I do care for Mike working off I'm Dave Defore. This has been the NBA Daily. We'll be back with more team previews and probably more Kauai Clippers News.
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Episode: Does the NBA have enough to punish the Clippers?
Date: September 16, 2025
Hosts: Dave DuFour (The Athletic) with guest Mike Vorkunov (covers sport/business at The Athletic)
Main Theme:
A deep dive into the ongoing investigation into the LA Clippers, owner Steve Ballmer, Kawhi Leonard, and a complicated web involving sponsorship, questionable investment, and potential NBA salary cap circumvention.
This episode addresses the ongoing NBA investigation into the Los Angeles Clippers’ potential circumvention of the salary cap regarding player Kawhi Leonard’s sponsorship ties with the company Aspiration—a relationship tangled with investments from Clippers owner Steve Ballmer, large money transfers, and connections to ongoing federal fraud charges. Dave DuFour and Mike Vorkunov break down key details, analyze the NBA’s investigatory capacity and standards, compare historical precedents, and contemplate the possible fallout for both the Clippers and the NBA’s public reputation.
Aspiration sponsorship deal:
Further complications:
Ongoing NBA investigation:
Investigation limitations:
Comparison to 1999-2000 Minnesota Timberwolves scandal:
Clippers case lacks direct evidence:
On the no-show and abnormal sponsorship:
Pattern of past Clippers’ questionable actions:
On the challenge for the NBA’s investigators:
“It's going to be interesting to see where the NBA goes. I think the pressure publicly is on them to do something... But it's also who can we talk to to find out about the, you know, who, what, when and where and why?” — Mike Vorkunov [07:08]
On the Timberwolves’ smoking gun:
“They had the act of impropriety, not just the mere appearance of impropriety. And they took away five first round picks... and they voided the contract.” — Mike Vorkunov [15:47]
On the Clippers’ patterns and league reputation:
“It certainly seems like the Clippers are doing a lot of walking like a duck here.” — Dave DuFour [21:54]
“The biggest scandals are the ones that lean into our presumed assumptions.” — Mike Vorkunov [22:22]
On no direct evidence surfacing:
“I'd be shocked if there was any sort of smoking gun to the likes of which Glenn Taylor and Joe Smith had, where there's a contract that says, hey, wink, wink, this is just so that you sign with the Clipper.” — Dave DuFour [19:55]
On the league’s public perception:
“This is a business... that's based on public sentiment... If you feel like a team is out there not playing by the rules... it's got to be, I would assume, pretty deflating.” — Mike Vorkunov [24:22]
The conversation is analytical, skeptical, and at times, wry. The hosts tread the line between detailed reporting and skeptical commentary, highlighting the complexity of the case and the limits of NBA governance. The Clippers’ actions are cast as deeply suspicious but frustratingly hard to definitively rule as illegal, illustrating the opaque and messy overlap of sports, business, and league authority.
This episode serves as both an exposé on the evolving Clippers scandal and a meditation on the difficulties inherent in policing modern pro sports. The hosts urge listeners to stay tuned as the investigation (and potentially, more revelations) unfolds, emphasizing that this case might one day become standard reading in the annals of NBA governance—whether as a notorious rule-break or an indictment of the loopholes present in the system.