Amazon's AI jackpot: Its $8 billion Anthropic holdings are now worth $74 billion Amazon CEO Andy Jassy Fortune/Reuters Amazon's investment in Anthropic has become one of the most lucrative bets in the cloud giant's history. Amazon's original $8 billion investment in the AI startup has swelled into a stake worth roughly $74 billion on paper as Anthropic's valuation has soared, according to a quarterly filing from late April. In the filing, Amazon said that as of March 31, it held about $42.2 billion worth of Anthropic convertible notes and $32 billion worth of Anthropic nonvoting preferred stock. Taken together, those holdings were worth roughly $74.2 billion at that time. The value of these stakes may have risen further since then. Amazon's growing Anthropic holdings, accumulated through late 2023 to 2025, are coming into greater focus as the AI startup readies an initial public offering. On Monday, Anthropic said it had filed confidentially filed for an IPO .…