Michael Burry, the investor famed for profiting from the 2008 housing collapse, has established a sizable position betting against Oracle by purchasing long-dated put options equating to roughly 1% of the company’s outstanding float. In a note shared with select clients, Burry warned that Oracle’s legacy license businesses face structural decline as enterprises accelerate transitions to hyperscale cloud providers. He highlighted a slowdown in new license bookings—down 12% year-over-year in Q4—and cautioned that free cash flow could compress by up to 15% in fiscal 2027 if on-premise renewals continue to wane. Burry urged investors to consider alternative cloud plays offering higher growth visibility and cleaner balance sheets.

At NRF 2026 in New York, Oracle introduced its Retail Supply Chain Collaboration cloud service, designed to help retailers manage an increasingly volatile supplier landscape. Integrated with Oracle Retail Merchandising Foundation Cloud Service, the solution delivers AI-powered forecasting accuracy improvements of up to 25%, real-time alerts on potential disruptions, and streamlined workflows that cut supplier onboarding times by 30%. Retailers can issue urgent notifications directly to suppliers, automate product record creation at the SKU level via MFCS APIs, and track sustainability certifications and compliance audits through a unified portal. Paul Woodward, Global VP of Oracle Retail Products, emphasized that the platform helps protect margins and reputations by enabling proactive risk mitigation across procurement, production and distribution processes.

In a recent research upgrade, a leading Wall Street firm raised Oracle’s rating to Buy, citing a 34% year-over-year surge in cloud revenues and a 68% jump in Oracle Cloud Infrastructure bookings. Remaining performance obligations (RPOs) climbed 438% to $523 billion, underscoring strong demand visibility. The analyst noted that while Oracle’s net leverage ratio of 3.2x EBITDA and rising interest expenses represent potential headwinds, management’s guidance for mid-teens revenue growth in Q3 and a 20% operating margin expansion should alleviate default concerns. The report projects free cash flow growth of 18% annually over the next three fiscal years, driven by ongoing cost discipline and expanding high-margin cloud services.