Recently, I thought about one of the craziest investment bets in venture capital history. Imagine this: someone invests $500 million into an AI company, and if everything goes legally, the return could reach 60 times. But the investor is currently waiting in federal prison until 2049. This story is too absurd for fiction.

It all started in April 2022 when Sam Bankman-Fried, or SBF, wrote a check for $500 million to Anthropic through Alameda Research. At that time, ChatGPT didn't exist yet, and AI was far from the hype now. SBF immediately took 86% of the total Series B round worth $580 million and received about 8% equity. Seven months later? The FTX empire collapsed. In November 2022, CoinDesk exposed Alameda’s balance sheet, Zhao Changpeng announced the sale of FTT, and everything collapsed within 9 days. SBF was arrested, extradited, and tried.

The most interesting part is the judge’s decision during the trial. SBF’s defense team tried to use the investment in Anthropic as evidence that he had a “vision” and was not just a scammer. They argued: look, its valuation increased multiple times, this isn’t a foolish decision. But prosecutor Damian Williams responded very sharply. He said: regardless of whether this investment was profitable or not, it’s completely irrelevant to the fraud charges. You stole other people’s money, and even if the investment was profitable, it’s still theft. The judge agreed. Anthropic’s name was removed from the trial. This was a crucial ruling because it shows that investment outcomes cannot be used as an excuse for financial crimes.

Dario Amodei, founder of Anthropic, actually sensed red flags from the start. He remembered SBF as “someone bullish on AI and concerned about safety,” but he said there were “too many warning signs.” So he made a pragmatic decision: take the money, but isolate SBF within the governance structure. SBF received non-voting shares and was removed from the board. This decision later proved to be very smart.

But here’s the interesting part: if there were so many red flags that governance had to be isolated, why was the investment still made? The answer lies in the philosophy of Effective Altruism that connects them. SBF is a true believer in EA from the “earning to give” branch, which is radical. He left Wall Street to dive into crypto with the stated goal of “altruism” — generating as much money as possible to donate. Meanwhile, Anthropic’s mission of “developing AI safely” is almost a standard EA recipe for existential risk.

Their connection isn’t coincidental. Dario Amodei lives in the same house as Holden Karnofsky, co-founder of GiveWell and Open Philanthropy, one of the most influential fund allocators in the EA movement. Early investors in Anthropic included Dustin Moskovitz from Facebook and Jaan Tallinn from Skype, both major EA funders. The Series A in 2021 was led by Tallinn, and Series B in 2022 was taken over by SBF. This isn’t about brilliant investment vision; it’s about EA money flowing into EA projects within a closed social network.

Now, fast forward to February 2026. Anthropic closed a funding round G worth $30 billion with a valuation of $380 billion. If there was no dilution, SBF’s 8% would theoretically increase from the original $40 million to over $30 billion. But the FTX bankruptcy liquidation team didn’t take this option. They sold shares in the first auction in March 2024 with a valuation of $884 million, generating a total of $1.34 billion from two rounds. This fund became a key source for creditor compensation and victim withdrawals.

From the liquidator’s perspective, this decision makes sense. They need cash now to pay creditors, not wait for a speculative future valuation. But the difference in numbers—$1.34 billion versus the potential $30 billion—is the biggest loss in the entire FTX bankruptcy case. That’s a huge opportunity cost.

The most ironic part is Anthropic’s current position. The company systematically distances itself from the EA label despite being built on EA logic. Seven co-founders committed to donating 80% of their personal wealth; the current valuation implies about $38 billion from that commitment alone. Nearly 30 Anthropic employees attend EA meetups, more than twice the combined number of OpenAI, Google DeepMind, xAI, and Meta. But Daniela Amodei told Wired in an interview: “I’m not an effective altruism expert. I don’t agree with that term.”

This stance — “take EA money, use EA people, live in an EA house, but don’t call it EA” — makes more sense after the SBF case. The FTX collapse brought EA’s reputation to its lowest point. Anthropic needs to maintain brand distance from this label, just like other smart companies that cut ties when their brand is associated with negative perceptions.

But the fact remains: Anthropic’s logic stems from core EA arguments about AI existential risk; its initial funding was almost entirely from the EA network; its governance structure is controlled by EA system people. And amid all this, the $500 million check from SBF remains the strangest page in company history.

SBF is now in federal prison, eligible for release as early as 2049 at age 57. Meanwhile, the company he invested in with stolen money has reached a valuation of $380 billion and become a central player in the AI arms race with the Pentagon. If everything is legal, that $500 million bet could be one of the highest-return venture bets of this era.

Both grew on the same ground. On that ground, Dario and SBF once attended the same party, adopted the same philosophy, but ended up in very different places. One in the AI kingdom with a valuation of $380 billion, the other in federal prison. Meanwhile, the $500 million check connecting them remains the weirdest page in Anthropic’s history.