Premium: The Hater’s Guide To Oracle (Part 2)

A critical deep-dive into Oracle's financial health arguing the company has been in a slow decline for nearly a decade, surviving through aggressive acquisitions, customer price gouging, and accounting maneuvers rather than organic growth. The piece contends that Oracle's massive bet on AI infrastructure — including $55.6 billion in capex in FY2026 alone and a $300 billion deal with OpenAI — has broken its historically conservative financial discipline, pushing free cashflow negative for the first time since 2001 and tripling its debt to $167.4 billion. The author believes Oracle's AI overcommitment will ultimately be what kills the company.