In 2021, Sam Bankman-Fried (SBF), founder of the cryptocurrency exchange FTX, invested $500 million in AI company Anthropic through his hedge fund Alameda Research, acquiring approximately 8% equity. At that time, the AI boom had not yet begun, and this investment was regarded as a highly forward-looking high-stakes bet. However, in 2022, SBF’s empire collapsed due to the FTX crisis, and his assets were liquidated. FTX eventually sold its Anthropic stake in two installments, reclaiming approximately $1.4 billion in total—three times the original investment. Yet, if the stake had been held until September 2025, when Anthropic completed its Series F financing with a valuation of $183 billion, the theoretical value of the equity would have reached around $14.6 billion, representing a potential profit of over $14 billion. During the trial, SBF’s team attempted to use this investment to prove his investment acumen, but prosecutors emphasized that the funds came from customer assets and were proceeds of financial fraud. This investment, which could have gone down in history, was reduced to a farce due to SBF’s crimes.

Authors | Lin Bai, Crow AI Talk

Last week, Anthropic announced the completion of its $13 billion Series F financing, with its valuation surging to $183 billion.

As soon as the news broke, netizens immediately thought of one name—SBF. Some sighed that if he hadn’t "gotten into trouble," this investment might have directly ranked among the "top five best investments in history."

Who is SBF? A post-90s individual who rose to fame overnight through cryptocurrencies. In just three years, he went from an unknown figure to the "king of the crypto world," with a peak net worth of $26 billion, firmly securing a spot in the Top 50 of the U.S. Rich List.

Back in 2021, when AI was far from as popular as it is today, SBF suddenly entered the AI track, investing $500 million in Anthropic and securing an 8% stake outright.

In today’s context, this would be the kind of legendary story Silicon Valley loves to hype: "A genius young man who bet on the future."

Unfortunately, fate has a penchant for dark humor. In 2022—the very year the AI boom took off—SBF’s empire came crashing down. All his assets, including this Anthropic stake, were packaged and sold by the liquidation team, ultimately fetching only $1.4 billion.

If the stake had been held until now, based on Anthropic’s latest valuation, the 8% equity would be worth approximately $14.6 billion (though this figure may be lower due to equity dilution)—a full ten times the selling price.

This is SBF’s farce: a post-90s "madman" in the crypto world, using money from others’ pockets, almost made an investment myth that could have gone down in history. Regrettably, before becoming a legend, he first became a cautionary tale.

You may not have heard of Sam Bankman-Fried (SBF), but in the crypto world, he is nothing short of a legend.

He was the owner of FTX, once the world’s third-largest cryptocurrency exchange, with the company’s valuation soaring to $32 billion at one point. Meanwhile, he also controlled the hedge fund Alameda Research, whose book assets peaked at $14.6 billion.

At the height of his fame, SBF’s net worth catapulted him to the 41st position on the Forbes U.S. Rich List, standing side by side with Silicon Valley tech tycoons.

If FTX is viewed as a "digital asset bank," then Alameda is more like a "fund company that both makes investments and trades cryptocurrencies itself." On one hand, it helps clients allocate cryptocurrency investment portfolios; on the other hand, it uses its own capital for venture capital.

From 2021 to 2022, SBF suddenly shifted his focus from virtual currencies to the real world. He directly instructed Alameda to borrow money, embarking on large-scale venture capital investments and pouring funds into non-crypto sectors—this was both a bet on the future and an attempt to diversify his risks. Among these bets, Anthropic stood out.

In 2021, SBF made a bold move, leading Alameda to spearhead Anthropic’s Series B financing. In that round, Anthropic raised a total of $580 million, with Alameda contributing $500 million alone, accounting for nearly 8% of the company’s equity.

It’s important to note that at that time, ChatGPT had not yet gained mainstream attention, and AI was nowhere near as popular as it is today. From an outsider’s perspective, SBF’s move was nothing short of a high-stakes gamble on the future.

What’s more interesting is that there was a touch of "idealism" behind this investment.

SBF considered himself a follower of Effective Altruism (EA). The core logic of EA is that doing good should not rely solely on compassion; instead, it should emphasize the cost-benefit ratio. In simple terms, with the same amount of money, one should strive to help more people and create greater social value.

Anthropic positioned itself as a "safety-first" large-model laboratory, dedicated to researching ways to reduce AI risks—an objective that perfectly aligned with the philosophy of the EA community. Additionally, early investors included EA heavyweights like Jaan Tallinn, co-founder of Skype. This made the investment seem like a combination of idealism and capitalism.

In this way, SBF led Alameda to invest $500 million in Anthropic, helping the company build a large-scale computing power infrastructure and research facilities.

If the story had ended here, it would have been a classic tale of "a genius young man in the crypto world who bet correctly on the future."

But fate had other plans. In November 2022, crypto media outlet CoinDesk exposed Alameda’s financial statements, uncovering the secret behind the house of cards:

One-third of its $14.6 billion in assets consisted of FTT—the native token issued by FTX itself.

What did this mean? Alameda obtained FTT at a low price, then drove up its market value by hoarding the token. It then used these tokens as collateral to borrow money from FTX, and subsequently used the borrowed funds for high-leverage investments, creating an internal cycle of capital.

As soon as the exposé was published, the market panicked and began selling off FTT, causing its price to plummet. Alameda and FTX collapsed one after another, and SBF’s empire crumbled in an instant.

Entering the liquidation phase, the Anthropic stake became the top asset targeted by FTX’s creditors. In 2023, as Google and Amazon entered the fray, Anthropic’s valuation skyrocketed, turning its stake into a "golden chip" in FTX’s asset portfolio.

The popularity of Anthropic even affected the sale of this stake. Due to the large number of potential buyers and the lengthy due diligence process, the sale was temporarily suspended.

It wasn’t until 2024 that FTX sold its Anthropic shares in two installments:

In the first sale, it offloaded two-thirds of the stake, reclaiming $884 million. It is said that 24 institutional investors participated in the subscription to split these shares, with the largest buyer being a sovereign wealth fund from Abu Dhabi.

In the second sale, FTX sold the remaining approximately one-third of its holdings (about 15 million shares), reclaiming $450 million and completely divesting itself of Anthropic equity.

In total, the FTX liquidation team recovered nearly $1.4 billion through the sale of the Anthropic stake—almost three times SBF’s original investment.

Ironically, if these shares had been held until September 2025, when Anthropic completed its latest round of financing (with a post-money valuation of $183 billion), the theoretical value of the 8% stake could have reached as high as $14.6 billion, representing a full $14 billion in profit. But in reality, the money had long been turned into "life-saving funds" in the liquidation pool.

Even more dramatic is that this investment was later brought up during SBF’s trial.

SBF’s defense attorney emphasized: "SBF is not someone who just wastes money recklessly. He invested in an AI company whose valuation later skyrocketed—this proves he has foresight and business acumen."

But the prosecution directly pushed back:

"SBF’s funds were not clean, self-owned capital; they were ‘moved’ from FTX customers’ pockets. Even if there was a book profit, it cannot wash away the original sin of financial fraud, nor can it dress up ‘intentional misappropriation’ as ‘investment error.’"

In the end, in October 2023, U.S. prosecutors filed a motion clearly stating:

"The defendant used customer funds to invest in Anthropic—this is an extension of his criminal methods, not evidence in his favor."

The irony is that it was this post-90s "madman" in the crypto world who almost made the most successful investment in AI history. Unfortunately, he never lived to see that day.

In 2021, Sam Bankman-Fried (SBF), founder of the cryptocurrency exchange FTX, invested $500 million in AI company Anthropic through his hedge fund Alameda Research, acquiring approximately 8% equity. At that time, the AI boom had not yet begun, and this investment was regarded as a highly forward-looking high-stakes bet. However, in 2022, SBF’s empire collapsed due to the FTX crisis, and his assets were liquidated. FTX eventually sold its Anthropic stake in two installments, reclaiming approximately $1.4 billion in total—three times the original investment. Yet, if the stake had been held until September 2025, when Anthropic completed its Series F financing with a valuation of $183 billion, the theoretical value of the equity would have reached around $14.6 billion, representing a potential profit of over $14 billion. During the trial, SBF’s team attempted to use this investment to prove his investment acumen, but prosecutors emphasized that the funds came from customer assets and were proceeds of financial fraud. This investment, which could have gone down in history, was reduced to a farce due to SBF’s crimes.

Authors | Lin Bai, Crow AI Talk

Last week, Anthropic announced the completion of its $13 billion Series F financing, with its valuation surging to $183 billion.

As soon as the news broke, netizens immediately thought of one name—SBF. Some sighed that if he hadn’t "gotten into trouble," this investment might have directly ranked among the "top five best investments in history."

Who is SBF? A post-90s individual who rose to fame overnight through cryptocurrencies. In just three years, he went from an unknown figure to the "king of the crypto world," with a peak net worth of $26 billion, firmly securing a spot in the Top 50 of the U.S. Rich List.

Back in 2021, when AI was far from as popular as it is today, SBF suddenly entered the AI track, investing $500 million in Anthropic and securing an 8% stake outright.

In today’s context, this would be the kind of legendary story Silicon Valley loves to hype: "A genius young man who bet on the future."

Unfortunately, fate has a penchant for dark humor. In 2022—the very year the AI boom took off—SBF’s empire came crashing down. All his assets, including this Anthropic stake, were packaged and sold by the liquidation team, ultimately fetching only $1.4 billion.

If the stake had been held until now, based on Anthropic’s latest valuation, the 8% equity would be worth approximately $14.6 billion (though this figure may be lower due to equity dilution)—a full ten times the selling price.

This is SBF’s farce: a post-90s "madman" in the crypto world, using money from others’ pockets, almost made an investment myth that could have gone down in history. Regrettably, before becoming a legend, he first became a cautionary tale.

You may not have heard of Sam Bankman-Fried (SBF), but in the crypto world, he is nothing short of a legend.

He was the owner of FTX, once the world’s third-largest cryptocurrency exchange, with the company’s valuation soaring to $32 billion at one point. Meanwhile, he also controlled the hedge fund Alameda Research, whose book assets peaked at $14.6 billion.

At the height of his fame, SBF’s net worth catapulted him to the 41st position on the Forbes U.S. Rich List, standing side by side with Silicon Valley tech tycoons.

If FTX is viewed as a "digital asset bank," then Alameda is more like a "fund company that both makes investments and trades cryptocurrencies itself." On one hand, it helps clients allocate cryptocurrency investment portfolios; on the other hand, it uses its own capital for venture capital.

From 2021 to 2022, SBF suddenly shifted his focus from virtual currencies to the real world. He directly instructed Alameda to borrow money, embarking on large-scale venture capital investments and pouring funds into non-crypto sectors—this was both a bet on the future and an attempt to diversify his risks. Among these bets, Anthropic stood out.

In 2021, SBF made a bold move, leading Alameda to spearhead Anthropic’s Series B financing. In that round, Anthropic raised a total of $580 million, with Alameda contributing $500 million alone, accounting for nearly 8% of the company’s equity.

It’s important to note that at that time, ChatGPT had not yet gained mainstream attention, and AI was nowhere near as popular as it is today. From an outsider’s perspective, SBF’s move was nothing short of a high-stakes gamble on the future.

What’s more interesting is that there was a touch of "idealism" behind this investment.

SBF considered himself a follower of Effective Altruism (EA). The core logic of EA is that doing good should not rely solely on compassion; instead, it should emphasize the cost-benefit ratio. In simple terms, with the same amount of money, one should strive to help more people and create greater social value.

Anthropic positioned itself as a "safety-first" large-model laboratory, dedicated to researching ways to reduce AI risks—an objective that perfectly aligned with the philosophy of the EA community. Additionally, early investors included EA heavyweights like Jaan Tallinn, co-founder of Skype. This made the investment seem like a combination of idealism and capitalism.

In this way, SBF led Alameda to invest $500 million in Anthropic, helping the company build a large-scale computing power infrastructure and research facilities.

If the story had ended here, it would have been a classic tale of "a genius young man in the crypto world who bet correctly on the future."

But fate had other plans. In November 2022, crypto media outlet CoinDesk exposed Alameda’s financial statements, uncovering the secret behind the house of cards:

One-third of its $14.6 billion in assets consisted of FTT—the native token issued by FTX itself.

What did this mean? Alameda obtained FTT at a low price, then drove up its market value by hoarding the token. It then used these tokens as collateral to borrow money from FTX, and subsequently used the borrowed funds for high-leverage investments, creating an internal cycle of capital.

As soon as the exposé was published, the market panicked and began selling off FTT, causing its price to plummet. Alameda and FTX collapsed one after another, and SBF’s empire crumbled in an instant.

Entering the liquidation phase, the Anthropic stake became the top asset targeted by FTX’s creditors. In 2023, as Google and Amazon entered the fray, Anthropic’s valuation skyrocketed, turning its stake into a "golden chip" in FTX’s asset portfolio.

The popularity of Anthropic even affected the sale of this stake. Due to the large number of potential buyers and the lengthy due diligence process, the sale was temporarily suspended.

It wasn’t until 2024 that FTX sold its Anthropic shares in two installments:

In the first sale, it offloaded two-thirds of the stake, reclaiming $884 million. It is said that 24 institutional investors participated in the subscription to split these shares, with the largest buyer being a sovereign wealth fund from Abu Dhabi.

In the second sale, FTX sold the remaining approximately one-third of its holdings (about 15 million shares), reclaiming $450 million and completely divesting itself of Anthropic equity.

In total, the FTX liquidation team recovered nearly $1.4 billion through the sale of the Anthropic stake—almost three times SBF’s original investment.

Ironically, if these shares had been held until September 2025, when Anthropic completed its latest round of financing (with a post-money valuation of $183 billion), the theoretical value of the 8% stake could have reached as high as $14.6 billion, representing a full $14 billion in profit. But in reality, the money had long been turned into "life-saving funds" in the liquidation pool.

Even more dramatic is that this investment was later brought up during SBF’s trial.

SBF’s defense attorney emphasized: "SBF is not someone who just wastes money recklessly. He invested in an AI company whose valuation later skyrocketed—this proves he has foresight and business acumen."

But the prosecution directly pushed back:

"SBF’s funds were not clean, self-owned capital; they were ‘moved’ from FTX customers’ pockets. Even if there was a book profit, it cannot wash away the original sin of financial fraud, nor can it dress up ‘intentional misappropriation’ as ‘investment error.’"

In the end, in October 2023, U.S. prosecutors filed a motion clearly stating:

"The defendant used customer funds to invest in Anthropic—this is an extension of his criminal methods, not evidence in his favor."

The irony is that it was this post-90s "madman" in the crypto world who almost made the most successful investment in AI history. Unfortunately, he never lived to see that day.