Tag: OpenAI

Credit markets often see trouble before equity investors do. Oracle’s current credit metrics have deteriorated so rapidly that Morgan Stanley analysts now warn spreads could approach 2008 financial crisis levels. The numbers suggest we’re watching a high-stakes gamble that could reshape enterprise software.

Oracle has executed significant workforce reductions at two critical junctures: during the 1990 near-bankruptcy and again in 2024-2025. In my view, this pattern isn’t coincidence. It may be Oracle’s most reliable leading indicator of strategic overextension.

Oracle’s September 2025 announcement of $455 billion in Remaining Performance Obligations deserves careful scrutiny, especially when examined through the lens of ASC 606 revenue recognition requirements.

The Headline That Moved Markets

Oracle prominently featured its $455 billion RPO (up 359% year-over-year) at the very top of its Q1 earnings release, even above revenue and earnings per share.¹ CEO Safra Catz declared Oracle expects to sign additional multi-billion-dollar customers, projecting RPO would “likely exceed half a trillion dollars” soon.²

This is Part 2 of a six-part investigative series analyzing Oracle’s $300 billion OpenAI partnership and the financial risks it creates. Each article examines a different dimension of what may be the most consequential bet in enterprise technology history.

Series Note: This is Part 1 of a 6-part analysis examining Oracle’s financial risks through the lens of someone who spent six years inside the company.

Having analyzed corporate risk patterns throughout my career in technology and product management, what’s unfolding with Oracle Corporation bears an unsettling resemblance to the company’s 1990 near-bankruptcy crisis. The numbers tell a story that should concern anyone invested in Oracle or considering its services.