FTX collapsed overnight, yet its most successful investment turned out to be Anthropic, the company behind Claude. If they hadn’t sold, those shares would now be worth over $100 billion. In 2021, SBF invested $500 million in Anthropic, initially acquiring about 13.56% of the company. After FTX’s collapse, the company sold all its Anthropic shares in 2024 to repay creditors, recovering approximately $1.3 billion. Turning $500 million into $1.3 billion is already a substantial gain—but when compared to the subsequent AI boom, it pales in comparison. If Anthropic’s IPO valuation reached $1.5 trillion, FTX’s original 13.56% stake would theoretically be worth $203.4 billion. Of course, equity dilution would occur. Even using the 7.84% stake FTX held at the time of its 2024 sale—and assuming no further dilution—those shares would now be worth $117.6 billion. Yet FTX actually sold for just $1.3 billion, leaving a gap of $116.3 billion. While this is purely hypothetical and not an actual realized loss, it’s still heartbreaking to contemplate. Although SBF caused massive damage to the crypto world, he undeniably demonstrated exceptional insight in investing in Anthropic. Had he not misappropriated funds and driven FTX into bankruptcy, that single investment alone could have made SBF a towering figure in both crypto and AI investing today. Unfortunately, one misstep led to eternal regret.