Anthropic's May 2026 Series H round at a $965 billion post-money valuation, followed by secondary market marks near $968 billion and plans for a potential November IPO targeting over $2 trillion, underpins the 92.5% market-implied probability that it will hold a higher valuation than OpenAI by December 31. Its annualized revenue run rate reached $65 billion by late July, reportedly surpassing OpenAI's in recent quarters amid 12-fold growth, while OpenAI's March round priced it at $852 billion and ongoing talks for $30 billion at roughly $1.4 trillion remain pre-IPO bridge financing. OpenAI's revenue run rate nears $70 billion but trails on disclosed efficiency metrics. Key catalysts include Anthropic's S-1 details and any OpenAI funding close before year-end, though shifts in investor multiples or execution risks could narrow the gap.