Nine months ago, Oracle was the hottest stock in enterprise technology. On September 10, 2025, shares surged 36% in a single session after reports surfaced that OpenAI had committed to a $300 billion, five-year cloud computing deal with the company. The stock hit a record high of $345.72. The narrative was irresistible: Oracle had reinvented itself as an AI infrastructure company, and the biggest name in artificial intelligence had just bet hundreds of billions on that transformation.