The NBA is investigating the LA Clippers and team owner Steve Ballmer over allegations that star player Kawhi Leonard accepted a $28 million endorsement as a way to get around the league’s salary cap. The endorsement deal was with the now-defunct sustainable banking company Aspiration—a company in which Ballmer has invested. Nate and Maria talk about whether Ballmer tried to take a page out of the mob playbook, and how the league could deter this kind of behavior in the future. 

Plus: Nate and Maria discuss a report from the Citizens Budget Commission that claims that New York’s share of millionaires is falling—and with it, the potential for revenue generation from taxes.

Further Reading:

From Pablo Torre Finds Out: Kawhi Leonard Signed a Secret $28M Deal. Steve Ballmer Funded a Fraud. We Followed the Money.

Citizens Budget Commission Report: The Hidden Cost of New York’s Shrinking Millionaire Share 

From the New York Times: New York Needs More Millionaires, Fiscal Watchdog Says”

For more from Nate and Maria, subscribe to their newsletters:

The Leap from Maria Konnikova

Silver Bulletin from Nate Silver 

The NBA is investigating the LA Clippers and team owner Steve Ballmer over allegations that star player Kawhi Leonard accepted a $28 million endorsement as a way to get around the league&rsquo;s salary cap. The endorsement deal was with the now-defunct sustainable banking company Aspiration&mdash;a company in which Ballmer has invested. Nate and Maria talk about whether Ballmer tried to take a page out of the mob playbook, and how the league could deter this kind of behavior in the future.&nbsp;
Plus: Nate and Maria discuss a report from the Citizens Budget Commission that claims that New York&rsquo;s share of millionaires is falling&mdash;and with it, the potential for revenue generation from taxes.
Further Reading:
From Pablo Torre Finds Out:&nbsp;<a href="https://www.youtube.com/watch?v=1OwzYk6OCFM">Kawhi Leonard Signed a Secret $28M Deal. Steve Ballmer Funded a Fraud. We Followed the Money</a>.
Citizens Budget Commission Report: <a href="https://cbcny.org/research/hidden-cost-new-yorks-shrinking-millionaire-share">The Hidden Cost of New York&rsquo;s Shrinking Millionaire Share</a>&nbsp;
From the New York Times:&nbsp;<a href="https://www.nytimes.com/2025/08/28/nyregion/nyc-millionaires.html">New York Needs More Millionaires, Fiscal Watchdog Says</a>&rdquo;
For more from Nate and Maria, subscribe to their newsletters:
<a href="https://mariakonnikova.substack.com/">The Leap</a>&nbsp;from Maria Konnikova
<a href="https://www.natesilver.net/">Silver Bulletin&nbsp;</a>from Nate Silver&nbsp;

Risky Business is a weekly podcast about making better decisions. The hosts, Maria Konnikova and Nate Silver, are both journalists who moonlight as high-stakes poker players. On Risky Business, they bring their analytical framework to everything from politics to poker to personal decisions.

Maria has a PhD in psychology and is the author of several books including, most recently, The Biggest Bluff. While researching the book, she inadvertently became a professional poker player, with over $500,000 in tournament winnings. She is a PokerStars Team Pro.

Nate is the founder and former editor-in-chief of FiveThirtyEight, and one of the country’s leading election forecasters. He has over $800,000 in lifetime poker tournament winnings and his forthcoming book, On the Edge, is about gambling and risk.

Risky Business is a co-production of iHeart Media and Pushkin Industries.

Risky Business is a weekly podcast about making better decisions. The hosts, Maria Konnikova and Nate Silver, are both journalists who moonlight as high-stakes poker players. On Risky Business, they bring their analytical framework to everything from politics to poker to personal decisions.
Maria has a PhD in psychology and is the author of several books including, most recently, The Biggest Bluff. While researching the book, she inadvertently became a professional poker player, with over $500,000 in tournament winnings. She is a PokerStars Team Pro.
Nate is the founder and former editor-in-chief of FiveThirtyEight, and one of the country’s leading election forecasters. He has over $800,000 in lifetime poker tournament winnings and his forthcoming book, On the Edge, is about gambling and risk.
Risky Business is a co-production of iHeart Media and Pushkin Industries.

Risky Business with Nate Silver and Maria Konnikova

Risky Business is a weekly podcast about making better decisions. The hosts, Maria Konnikova and Nate Silver, are both journalists who moonlight as high-stakes poker players. On Risky Business, they bring their analytical framework to everything from politics to poker to personal decisions.
Maria has a PhD in psychology and is the author of several books including, most recently, The Biggest Bluff. While researching the book, she inadvertently became a professional poker player, with over $500,000 in tournament winnings. She is a PokerStars Team Pro.
Nate is the founder and former editor-in-chief of FiveThirtyEight, and one of the country’s leading election forecasters. He has over $800,000 in lifetime poker tournament winnings and his forthcoming book, On the Edge, is about gambling and risk.
Risky Business is a co-production of iHeart Media and Pushkin Industries.

Did the LA Clippers Take a Page from the Mob?

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/9b82e8a5-7d46-4e8a-93a0-b364013c9eb3/transcript

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