I found an interesting story. Currently, Anthropic's market capitalization exceeds $380 billion, but the story of its initial investment is truly complex.

In April 2022, SBF poured $500 million into Anthropic's B-Round. At that time, ChatGPT hadn't even been released yet, and attention to AI wasn't as high as it is now. That investment accounted for 86% of the total. If everything was legal, based on the current valuation, the 8% stake at that time would theoretically be worth over $30 billion. Because $500 million would become $30 billion, the return is over 60 times. One of the top profits in venture capital history.

But the problem is, that $500 million came from FTX customer deposits. Seven months later, FTX collapsed.

In fact, SBF and Dario were part of the same community. The world of Effective Altruism (EA), a philosophy that aims to mathematically optimize charitable activities. They lived in the same apartment, attended the same parties, and read the same papers. Dario was connected with some influential figures within this community.

SBF was part of a particularly radical faction within EA, advocating "earning to give." Making a lot of money through crypto assets and then allocating it to the "greatest good." Meanwhile, Anthropic's mission was "developing safe and powerful AI," which is exactly the standard solution EA advocates for AI risks. That’s why SBF invested in Anthropic. It wasn’t just a financial decision; it was a flow of funds among people sharing the same philosophy.

However, Dario wasn't naive. In later interviews, he said he felt "sufficient red flags" about SBF's behavior. So, he accepted the funds but isolated them within governance structures. He gave SBF non-voting shares and excluded him from the board.

In November 2022, CoinDesk exposed Alameda’s balance sheet. A bank withdrawal rush ensued, and FTX was gone in nine days. SBF was arrested and sentenced to 25 years in prison in March 2024. All assets, including the 8% stake in Anthropic, were frozen.

An interesting event happened during the liquidation auction. In March 2024, at an $880 million valuation, the first round took place. Mubadala, the sovereign fund of Abu Dhabi, invested $500 million. This was exactly the same amount SBF had invested at the time. Jane Street was also listed as a buyer. SBF’s former employer was buying back shares purchased with illicit funds by former employees.

A total of $1.34 billion was recovered across two rounds. This money flowed into FTX’s creditor compensation pool.

But here’s the point of regret. What if the liquidation team hadn’t sold? By February 2026, Anthropic completed a $30 billion G-Round, and its post-investment valuation reached $380 billion. Without considering dilution, that 8% would have been worth more than $30 billion, up from $1.34 billion.

SBF, currently serving time in a federal prison, is 57 years old. He could be released as early as 2049. During that time, the AI companies he invested in with illicit funds have surpassed a $380 billion market cap, and negotiations are underway with the Pentagon over AI weaponization. If everything had been legal, SBF would have been one of the most highly profitable venture capitalists of this era.

Anthropic and SBF grew from the same soil. The same EA community, the same parties, the same philosophy. One is heading toward a $380 billion AI empire, the other toward federal prison. The $500 million check that connected these two remains the most mysterious page in Anthropic’s history to this day.