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🍋 LeBond James

🍋 LeBond James

Plus: Canada hit back with 50% tariffs, OpenAI is challenging Nvidia with its own chip, and Anthropic is pitching a $30 trillion revenue opportunity.

Short Squeez
August 26, 2026

Together With

"If you always want more, then you'll find the most you can have will always be too little." — James Clear

Good Morning! Canada fired back in the trade war and is enacting up to 50% tariffs on US goods. Thoma Bravo had to make 40 creditor-friendly concessions in debt restructuring talks for cybersecurity firm Proofpoint. And Stanley Druckenmiller dropped a WSJ op-ed criticizing Bessent for his bond market intervention that he admitted was written with AI.

OpenAI says its Jalapeño chip can power faster AI responses than Nvidia's. Anthropic is planning to tell investors its potential revenue opportunities exceed $30 trillion based on total addressable market. And investors are snapping up hotels and fixing them up, with hotel sales rising 28% in the first half of the year.

Plus: Why CEOs have a problem with workplace DMs, OnlyFans paid a $700 million dividend to its founder the year before he died, and private equity growth funds attracted record first-half inflows as the sector rebounds.

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SQUEEZ OF THE DAY

LeBond James

LeBron James pulled off one of the stranger pieces of financial engineering of the last decade: he turned himself into a bond. In 2018, while still with the Cavaliers, an LLC he controls called King James Funding sold nearly $300 million of bonds to two Midwestern life insurers whose portfolios were managed by Guggenheim Partners. The collateral was decades of future income, including his lifetime Nike deal. The bonds paid 4.8% and don't mature until 2049.

Instead of waiting 30 years for endorsement checks to trickle in, James pulled hundreds of millions into the present. It's the same logic behind any borrower sitting on a valuable asset: borrowing against it beats triggering a 40-50% tax bill by selling. He later paid part of it down and came back for more. In 2022, the same insurers bought ~$60 million of 34-year bonds at 5.75%, leaving ~$245 million of LeBron debt on their books at the end of last year.

Why two Midwestern insurers wanted this is the private credit story in a nutshell. A 30-year bond backed by one celebrity's future income is awkward for a bank or mutual fund to hold, but insurers sit on enormous pools of long-term capital and can lock money into illiquid assets for the extra yield.

Over the past decade, alternative managers have taken over more of that portfolio work and pushed well past corporate bonds into private credit, royalties, and bespoke assets. Insurers want yield, managers want permanent capital, and future Nike income fits neatly in the middle.

The Guggenheim link looks like a red flag until you check the timeline. Mark Walter, then Guggenheim's CEO, didn't take a minority Lakers stake until 2021, years after the original financing. By the 2022 deal, though, James played for the Lakers, Walter owned part of the team, and Guggenheim was an investor in SpringHill, James's media company with Maverick Carter. James's spokesperson said both financings were independently credit rated, that the 2022 transaction was NBA-approved, and that James has no affiliation with Guggenheim or the insurers beyond the deals themselves.

Nothing ties these bonds to the federal investigations now circling Walter's empire, and the insurers under scrutiny are different entities from the ones that funded James. But the timing makes the old deals worth a second look. What regulators are examining is more than $20 billion of loans Walter's insurers made to businesses he also controls, which is allowed but has to be disclosed, and wasn't.

Takeaway: Monetizing future income isn't new. Bowie did it with his catalog in 1997, and film and music rights have traded that way ever since. What's rarer is doing it against an athlete's endorsement income at this scale; a push to securitize Michael Jordan's Nike deal in the early 2000s never got done. James's spokesperson called the structure common at his level of earnings, but deals like this are private by construction, which is why one from 2018 is only surfacing now.

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HEADLINES

Markets Rundown

Market Update

Stocks rose as the 10-year Treasury yield fell to 4.62%, led by gains in technology and communications; energy underperformed.
WTI crude fell near $81 on reports the U.S. plans to return diplomats to the Middle East.
Asian equities finished higher overnight and European shares gained; the U.S. dollar weakened modestly.

Economic Data

ADP showed private employers added an average of 11,750 jobs per week for the four weeks ending August 8, up from 9,500.
The Conference Board's Consumer Confidence Index fell to 89.4 in August, below the 90.2 forecast, for a second straight monthly decline.
The unemployment rate remains at 4.1%, with 7.4 million job openings still above the 6.9 million unemployed.

Movers & Shakers

(+) Moderna ($MRNA) +14% after Wolfe Research upgraded the mRNA vaccine and biotech company to Peer Perform.
(+) Bloom Energy ($BE) +7% because former House Speaker Nancy Pelosi took an initial stake in the fuel cell energy company in late July.
(–) Dick’s Sporting Goods ($DKS) -31% after the sporting goods retailer missed Q2 profit and revenue estimates and cut its guidance.

Prediction Markets

Earnings Call Special (after markets close): Nvidia
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Private Dealmaking

Starcloud, a developer of orbital data centers, raised $250 million
Generalist, a developer of robot brains, raised $200 million
Emerald AI raised $150 million
Alice, an Israeli developer of AI safety and security layers, raised $140 million
Blank Street, a Brooklyn-based coffee chain, raised $105 million
Faye, a travel insurance startup, raised $50 million

For more PE, VC & M&A deals, subscribe to our Buysiders newsletter.

BOOK OF THE DAY

Money To Burn

Description:
William D. Cohan delivers a deeply reported account of Leon Black and the extraordinary rise of Apollo Global Management. The book traces Apollo from its origins in the aftermath of Drexel Burnham Lambert's collapse through its transformation into one of Wall Street's most powerful private equity and private credit firms. Cohan examines Apollo's aggressive investment strategy, the creation of Athene, the firm's internal power dynamics, and the controversies that ultimately led to Black's departure. It combines financial history, corporate intrigue, and the personal story of one of modern Wall Street's most consequential figures.

Book Length: 688 pages
Release Date: September 8, 2026

Ideal For:
Investors, private equity professionals, finance enthusiasts, and readers interested in Wall Street, Apollo, Leon Black, private credit, and the evolution of modern finance.

Apollo's story is ultimately a story about what happens when extraordinary financial ambition meets extraordinary risk.

DAILY VISUAL

VC 101

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DAILY ACUMEN

Explanatory Depth

Ask someone how a toilet works and most will say they understand it fine. Ask them to explain it step by step, and the confidence collapses almost immediately, revealing gaps they never noticed were there. This is the illusion of explanatory depth, the gap between how well we think we understand something and how well we could actually explain it.

This is dangerous in finance specifically, where familiarity gets mistaken for understanding constantly. Most people feel they understand a complex instrument or a company's business model, right up until they are asked to explain the actual mechanism out loud to someone skeptical, at which point the fluency reveals itself as surface level.

The test worth running before any real conviction is simple. Try explaining the position from scratch, mechanism by mechanism, to an imagined skeptic. The places where the explanation gets vague are exactly the places where the understanding was never really there.

ENLIGHTENMENT

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MEME-A-PALOOZA

Memes of the Day

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