By Jeremy Phillips
Publication Date: 2026-03-11 13:07:00
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A Guggenheim analyst doesn’t blink. Even as Oracle (NYSE:ORCL) The stock is down 23% year-to-date and is about 54% below its September 2025 highs. However, the company’s analyst did not meet the $400 price target. The call is simple and bold: “Free cash flow, this thing turns into a free cash flow waterfall in FY29 and FY30.”
That’s a thesis worth uncovering, because right now Oracle’s free cash flow looks anything but a waterfall. It looks like a drain.
The hole before harvest
Oracle is spending on a scale that would have been unimaginable just a few years ago. From fiscal 2018 to fiscal 2021, Oracle’s annual capital expenditures averaged approximately $1.7 billion. The investment forecast for the 2026 fiscal year is $50 billion. That’s not a typo.
The result? Trailing free cash flow is currently negative $24.7 billion. The Guggenheim analyst does not see this as a warning signal, but rather as confirmation that major efforts are now being made and revenue recognition…
