Vanity Fair Unravels Ellison's Octopus Empire

Vanity Fair published a feature by Tom Dotan on Larry Ellison on October 1. The article portrays the 82-year-old Oracle founder as part of a web spanning data centers, media, and politics, with his private investment firm named Cephalopod Corp.

The octopus is not just a metaphorical name. The funding entity for Lanai is Octopus Holdings LP, with Tentacle Corp as the general partner. The venture capital tool is called Tako Ventures, where 'tako' means octopus in Japanese, and past investments include NetSuite, Theranos, and Sensei Farms. An ukiyo-e print featuring an octopus hangs in his Lanai villa. A former executive joked that he is the octopus. In 2012, he bought Lanai from David Murdock for $300 million as reported, with about 3,000 permanent residents on the island. He owns the only gas station, cinema, another supermarket, and purchased the newspaper Lanai Today. Sensei Farms operates hydroponic greenhouses, claiming to be a thought leader in greenhouse produce after spending hundreds of millions over eight years. At the Four Seasons entrance, there is a bronze sculpture he commissioned from Damien Hirst titled Overcoming Adversity, featuring two octopus arms reaching out from the waves.

Oracle's arm is depicted as a 49-year-old database company transitioning to AI data centers. The article cites $130 billion in debt and negative free cash flow. In the last fiscal year, $43 billion in bonds were issued, capital expenditures more than doubled, and free cash flow fell to -$23.7 billion. On September 9, 2025, Safra Catz stated during an earnings call that the future billing for signed data centers totaled $317 billion. The next day, the stock price surged over 43%, marking the largest single-day increase since 1992, with Ellison briefly surpassing Elon Musk to become the world's richest person. The Wall Street Journal later clarified that $300 billion of this was attributable to a single client, OpenAI.

On the first full working day after Donald Trump resumed office, Stargate was announced, with Ellison, Sam Altman, and Masayoshi Son standing at the White House, with a project scale of $500 billion. Ellison stated that Oracle's data center in Abilene, Texas, along with OpenAI, was already under construction, with some contractors only learning they were working on Stargate after hearing this. Employees joked that Uncle Larry would pay. In July, S&P downgraded the rating to one notch above junk. The company withdrew plans for an expansion at the Abilene site. In September, a force majeure notice was issued for the New Mexico site, seeking to defer payments in case of project delays, with Oracle claiming progress is ongoing. The Financial Times reported that some related loan transactions were priced at about 90 cents. Since its peak, the stock price has dropped by more than half, with Ellison's net worth falling from around $400 billion at its peak to about $217 billion in September.

The media arm is represented by his son David Ellison. Skydance used his father's money to acquire Paramount and CBS News, and won Warner Bros. Discovery in an $110 billion deal. The consortium led by Oracle is working on the U.S. split of TikTok, with Oracle hosting U.S. user data and overseeing algorithm security. The political arm includes a $45 million donation to a pro-Trump nonprofit organization in 2024, a figure cited from the Wall Street Journal. He has also funded Tony Blair's nonprofit organization and hosted Benjamin Netanyahu at Lanai during his domestic corruption allegations. Bernie Sanders commented on the feature, stating that a family owning so much media and donating tens of millions to Trump and right-wing organizations raises questions about oligarchs and media ownership.

In June, he missed the Oracle earnings call for the first time in years. The last time he missed it was in 2013 to attend the America's Cup. He did not respond to multiple interview requests from Vanity Fair. In September 2025, cloud business president Clay Magouyrk and software head Mike Sicilia were appointed co-CEOs, with Catz stepping down but remaining as vice-chair of the board. Oracle publicly stated that OpenAI's latest model Astra is being trained in Abilene. Analysts summarized the optimistic scenario: for this data center bet to completely blow up, OpenAI would have to go to zero.

Equity and bonds are paying for the same capacity. The buyer is OpenAI's training demand, while the seller is Oracle, which bought Nvidia chips and facilities with bonds. Beneficiaries are the model companies that gain capacity and David Ellison, who is pushing Hollywood mergers with family funds. Those under pressure are the lenders who bought Oracle's debt at 90 cents and the competing bidders who failed to acquire Warner Bros. Discovery. The force majeure notice does not cancel the New Mexico project; it changes who pays cash first in case of delays.

Source: Public Information