There is a story in the crypto world that never ceases to fascinate me: how a scammer who is now serving 25 years in prison almost made the smartest investment in AI history. It all revolved around 500 million dollars.

It's April 2022. Sam Bankman-Fried, through his fund Alameda Research, invests half a billion dollars in Anthropic's Series B. At that time, ChatGPT didn't even exist; no one imagined that AI would become what it is today. SBF captures 86% of that $580 million round, holding about 8% of the company. Seven months later, FTX collapses. The empire crumbles in nine days after Alameda's problems are revealed. SBF ends up convicted, and it turns out that those $500 million were user funds, not legitimate capital.

The irony: if that investment had been legal, it would be worth a fortune today. Anthropic just closed its Series G in February 2026 at a valuation of $380 billion. The 8% that SBF theoretically acquired would have been worth over $30 billion. A 60-fold gain on $500 million. Throughout venture capital history, few returns reach that scale.

But here’s the fascinating part: this was not luck or brilliant vision. It was pure connection. Behind all this is an ecosystem called effective altruism (EA).

In mid-2010s San Francisco, a group of people shared homes, attended the same events, read the same papers. They believed charity should operate with mathematical logic: maximize impact per dollar. And they considered that the most serious existential risk was not nuclear war, but uncontrolled AI.

Dario Amodei, founder of Anthropic, was deeply immersed in this. He lived with Holden Karnofsky, co-founder of GiveWell, and Paul Christiano, an AI alignment researcher. Karnofsky later married Dario’s sister. This was the circle: people who knew each other, trusted, shared values.

SBF also belonged to this network. He adhered to the most radical branch of EA: "earn to give" (earn to donate). He left his job at Jane Street, launched into crypto with the public promise that he wasn’t seeking personal wealth, but accumulating money to allocate to causes with maximum impact.

Anthropic, with its mission to "develop powerful AI safely," was exactly the kind of project the EA ecosystem considered crucial. The three biggest historical sponsors of the EA movement were all initial investors in Anthropic: Dustin Moskovitz (co-founder of Facebook), Jaan Tallinn (co-founder of Skype), and SBF.

In May 2021, Tallinn led the $124 million Series A. A year later, SBF took the lead in Series B with his $500 million check.

Now, Dario was not naive. He later admitted that he perceived "enough red flags" in SBF. So he made a smart decision: accept the money but isolate it within the governance structure. SBF received shares without voting rights, was excluded from the board. Later, Dario described SBF’s behavior as "much more extreme and malicious than I imagined."

The obvious question: if there were so many warning signs, why did they accept it? Because in 2022, AI funding was scarce. Finding someone willing to contribute $500 million at once was nearly impossible, regardless of red flags. But there’s another more subtle reason: in the logic of the EA world, the origin of capital was never a priority. The important thing was effectiveness: if the money helps you do more good things, the means can be flexible.

This logic, taken to criminal extremes by SBF, in the moment of his investment in Anthropic, simply seemed like a bold philosophical choice but not illegal.

Then came November 2022. CoinDesk publishes Alameda’s balance sheet. Panic ensues. FTX collapses. SBF is arrested, extradited, tried. In March 2024, sentenced to 25 years. His shares in Anthropic, along with all his assets, are frozen in liquidation.

During the trial, defense lawyers tried to present the investment in Anthropic as evidence that SBF had "vision," that he made smart decisions. The prosecutor responded forcefully: you stole money from others to invest it. Even if you gained, you’re still a thief. The judge agreed. Anthropic’s name was excluded from the verdict.

Then came the liquidation auction. Abu Dhabi’s sovereign fund Mubadala invested exactly $500 million (the same amount SBF had put). Jane Street, the former company where SBF worked, also bought shares. In two rounds, $1.34 billion was recovered, money that went to a compensation fund for affected FTX users.

What would have happened if they hadn’t sold? Now, with Anthropic valued at $380 billion after its Series G in February 2026, that 8% would have been worth over $30 billion. The gap between the $19283746565748392T sold (and the potential $192837465657483904T) is the greatest loss in FTX’s entire bankruptcy.

Today, Anthropic deliberately distances itself from the EA movement. Its co-founders committed to donating 80% of their personal wealth but publicly avoid identifying with the term. Daniela Amodei (the founder’s sister, now at Anthropic), said in an interview: "I don’t identify with that term. My impression is that it’s a bit outdated."

That’s understandable. The collapse of FTX damaged the movement’s reputation. Anthropic needs to distance itself from that label.

But the facts are there: Anthropic was born from the core arguments of EA about existential AI risks; it was almost entirely funded by the EA network; its governance is controlled by people from the ecosystem.

SBF is now in federal prison. He will be released in 2049, at age 57. Meanwhile, the company where he invested $500 million with stolen money reached a valuation of $380 billion and participates in global debates on AI militarization with the Pentagon.

The irony is almost perfect: SBF’s "earn to give" and Anthropic’s "safe AI development" shared the same operating system. To achieve a sufficiently great good, both were willing to accept unusual means and risks. SBF crossed the line into crime. Anthropic operated on the safe side. But both grew in the same soil.

And that $500 million check remains the strangest page in Anthropic’s history.