Guggenheim analyst predicts Oracle free cash flow ‘waterfall’ in fiscal 29-30

• Oracle (ORCL) is down 23% year-to-date and 54% disconnected September 2025 highs astatine $149.40. The institution has $553B successful remaining show obligations, up 325% year-over-year, with FY2026 capex guidance astatine $50B versus trailing escaped currency travel of antagonistic $24.7B.

• Oracle’s monolithic datacenter buildout for AI infrastructure is depressing near-term escaped currency flow, but contracted gross of $553B ensures a crisp inflection erstwhile capableness comes online successful fiscal 2029 and 2030.

• The expert who called NVIDIA successful 2010 conscionable named his apical 10 AI stocks. Get them present FREE.

One Guggenheim expert isn't blinking. Even arsenic Oracle (NYSE:ORCL) banal sits down 23% year-to-date and astir 54% disconnected its September 2025 highs, the firm's expert hasn't touched the $400 terms target. The telephone is elemental and bold: "Free currency flow, this happening turns into a escaped currency travel waterfall successful fiscal 29 and 30."

That's a thesis worthy unpacking, due to the fact that close present Oracle's escaped currency travel looks thing but a waterfall. It looks similar a drain.

Oracle is spending astatine a standard that would person seemed unimaginable conscionable a fewer years ago. From FY2018 done FY2021, Oracle's yearly superior expenditures averaged astir $1.7 billion. FY2026 capex guidance sits astatine $50 billion. That's not a typo.

READ: The expert who called NVIDIA successful 2010 just named his apical 10 AI stocks

The result? Trailing escaped currency travel is presently antagonistic $24.7 billion. The Guggenheim expert sees this not arsenic a reddish flag, but arsenic confirmation that the dense lifting is happening now, and the gross designation comes later.

The expert adjacent flagged that gross borderline compression from the datacenter buildout is simply a positive signal, not a antagonistic one. It means important gross is inactive ahead, waiting to travel online erstwhile those datacenters are operational.

Here's what makes this thesis much than hope: Oracle has already sold the capableness it's building.

Remaining Performance Obligations, Oracle's contracted aboriginal gross backlog, deed $553 cardinal successful Q3 FY2026, up 325% year-over-year. Management was explicit astir what's driving it: "a question of large-scale AI contracts wherever customers either prepay oregon proviso GPUs directly."

CEO Safra Catz laid retired the OCI gross roadmap successful Q1 FY2026:

"We expect Oracle Cloud Infrastructure gross to turn 77% to $18 cardinal this fiscal twelvemonth — and past summation to $32 billion, $73 billion, $114 billion, and $144 cardinal implicit the consequent 4 years. Most of the gross successful this 5-year forecast is already booked successful our reported RPO."