Larry Ellison Was Once the World’s Richest Man. Now Oracle Is Down Over 50% While He Bankrolls His Son’s Fight to Control a $110 Billion Media Empire

By Danielle Liverance Published Jul 15, 9:04AM EDT

Quick Read

Oracle (ORCL) has shed 57% since September, halving the value of shares backing Ellison's $40.4 billion guarantee on the WBD merger.
Twelve state AGs sued to block the merger despite DOJ approval, putting a $7 billion termination fee at risk if the deal collapses.
Oracle's capex exploded to $56 billion in FY2026, flipping free cash flow to negative $24 billion despite 93% cloud infrastructure growth.
This lithium producer surpassed a $1B private valuation, joining some of America's most powerful startups. Now you can invest in EnergyX alongside global giants like General Motors, but only through July 16. (sponsor)

This post may contain links from our sponsors and affiliates, and Flywheel Publishing may receive compensation for actions taken through them.

Larry Ellison Was Once the World’s Richest Man. Now Oracle Is Down Over 50% While He Bankrolls His Son’s Fight to Control a $110 Billion Media Empire — © Kimberly White / Getty Images News via Getty Images

On Monday, July 13, 2026, two things hit Larry Ellison at once. Oracle (NYSE:ORCL | ORCL Price Prediction) extended a collapse that has erased more than half its value since September, and a coalition of 12 states sued to block the $110 billion media merger he is personally guaranteeing with $40.4 billion of his own money. Same fortune, same day, both directions.

From the Top of the World to No. 8

In September 2025, Ellison became just the second person, after Elon Musk, to cross $400 billion in net worth, peaking near $388 billion as Oracle hit $345.72 a share. By July 13, per Forbes, his net worth had fallen to roughly $175 billion, a decline of about $213 billion in under ten months, dropping him to No. 8 on the Bloomberg Billionaires Index. Oracle shares are down roughly 55-58% from their September peak, closing at $127.94 on July 14. June 2026 was Oracle’s worst month since September 1990; the week ending June 26 was its worst since August 2001, per CNBC.

Why Oracle Collapsed

Oracle reported Q4 FY2026 revenue of $19.184 billion with cloud infrastructure up 93% to $5.787 billion. The problem: spending. Capital expenditures exploded to $55.66 billion in FY2026, blowing past the company’s own $50 billion guidance. Free cash flow swung to negative $23.7 billion. Oracle left FY2027 revenue guidance at $90 billion despite a record backlog of $638 billion in remaining performance obligations, heavily concentrated in OpenAI, whose IPO has slipped to 2027. Management plans to raise another $40 billion in FY2027 through debt and equity, including a $20 billion share sale. Our earlier Oracle earnings preview flagged this capex-versus-cash-flow tension.

The $110 Billion Bet

On February 27, 2026, Paramount Skydance (NASDAQ:PSKY), led by chairman and CEO David Ellison, announced a definitive deal to acquire Warner Bros. Discovery (NASDAQ:WBD) at an enterprise value of roughly $110-111 billion, $31.00 per share in cash. The Justice Department approved it in June. Per SEC filings, the Ellison Family Trust provides a $45.7 billion equity backstop, and Ellison gave an irrevocable personal guarantee of $40.4 billion of the equity financing. The trust holds about 1.16 billion Oracle shares, now worth roughly half their value when the guarantee was made. Additional funding: $24 billion from Middle Eastern sovereign wealth funds and $57.5 billion in debt from Bank of America, Citi, and Apollo.

The 12-State Lawsuit

On Monday, a coalition of 12 states, led by California Attorney General Rob Bonta, sued to block the merger: California, Arizona, Colorado, Connecticut, Massachusetts, Minnesota, Nevada, New Jersey, New Mexico, New York, Oregon, and Washington, all Democratic AGs, defying DOJ approval. Their theory: the combined company would control 27% of wide-release theatrical distribution, 30% of anticipated blockbuster films, and 27% of the basic cable bundle. “The unlawful merger of these two entertainment behemoths would lead to higher prices, lower quality, and less content for film and television, harming movie theaters, basic cable distributors, and ultimately, audiences on every sofa and movie theater seat in the U.S.,” Bonta said. Hollywood mobilized in April, when more than 5,000 industry professionals, including Sofia Coppola, Kevin Bacon, Jane Fonda, and Robert De Niro, signed an open letter opposing the deal. Paramount countered that the suit “distorts settled antitrust law and is based on a misrepresentation of competition in the entertainment industry today,” and vowed to defend it.

The Ticking Clock and the Guarantee Math

Closing targets Q3 2026, but a “ticking fee” of $0.25 per quarter begins accruing after September 30 if the deal slips, costing Paramount hundreds of millions per quarter. A $7 billion regulatory termination fee applies if it collapses, on top of the $2.8 billion breakup fee Paramount already paid to Netflix. Here is the alarming piece: Ellison made his $40.4 billion guarantee near Oracle’s highs. With the stock down 55-58%, the trust’s 1.16 billion Oracle shares are worth roughly half as much, and Forbes has questioned whether Ellison has enough cash to honor the guarantee without selling Oracle stock or borrowing. Oracle’s share price is now a direct variable in whether the WBD deal closes as structured.

The Bottom Line for Investors

For Oracle, the exposure is the capex explosion, deeply negative free cash flow, and OpenAI concentration inside an otherwise real backlog. For Paramount Skydance, the 12-state suit is the biggest threat to closing on time, with ticking fees and litigation risk. WBD shareholders already approved the $31-per-share cash offer, and the stock traded at $27.48 on July 14, a spread reflecting deal uncertainty. Oracle’s recovery is now financially entangled with the WBD deal, because Ellison needs his Oracle shares to hold value to stand behind the guarantee.

The AI boom made Larry Ellison, briefly, the richest man alive. The AI spending cycle is now devouring Oracle’s cash flow. Twelve Democratic attorneys general are trying to stop his son’s media empire. And the $40.4 billion guarantee holding it all together is backed by a stock that has lost half its value.

Contact [email protected] for any questions or corrections.

Disclaimer: Energy Exploration Technologies, Inc. ("EnergyX") has engaged 24/7 Wall St to publish this communication in connection with EnergyX's ongoing Regulation A offering. 24/7 Wall St has been paid in cash and may receive additional compensation. 24/7 Wall St and/or its affiliates do not currently hold securities of EnergyX.

This compensation and any current or future ownership interest could create a conflict of interest. Please consider this disclosure alongside EnergyX's offering materials. EnergyX's Regulation A offering has been qualified by the SEC. Offers and sales may be made only by means of the qualified offering circular. Before investing, carefully review the offering circular, including the risk factors. The offering circular is available at invest.energyx.com/.

Comparisons to other companies are for informational purposes only and should not imply similar results. Past performance is not indicative of future results. Market shortfall are forward‑looking estimates and are subject to substantial uncertainty. Investments in private placements, and start-up investments in particular, are long-term, illiquid, speculative and involve a high degree of risk and those investors who cannot afford to lose their entire investment should not invest in start-ups

Follow 24/7 Wall St. on Google

About the Author Danielle Liverance →

I've spent more than 15 years inside enterprise software, working alongside the finance, sales operations, and HR leaders who run the revenue engines at some of the largest tech companies in the country.

My day job is helping enterprise executives make smarter decisions about retention, compensation, and growth. These are the same operational levers that show up in every earnings report investors actually read. That perspective shapes my writing for 24/7 Wall St.

The headline numbers are easy. The interesting stuff is underneath: how companies make money, what executives are worried about, and what any of it means for the person checking their 401(k) on a Sunday afternoon. I write about personal finance and business as someone who has spent her career inside the rooms where these decisions get made.