Inside Larry Ellison's Wide Web of Power, Money and Politics

PROLOGUE: THE ISLAND

The first sign was the orange Corvette.

In the early days of July, the residents of Lanai started seeing a C8 Stingray the color of a traffic cone tearing along the island’s switchback roads. Then other signals came. The clerk working the cigarette counter at the Pine Isle Market said her nephew, a private chef, had flown in and had been shopping for a big group.

At the Four Seasons down in Manele, the island’s pharmacist Kert Shuster was leaving brunch at Nobu when he saw a security detail he recognized moving through the lobby. It’d been a while, but Shuster knew—he’d just missed Larry Ellison.

A few years had passed, it seemed, since the man who owns all but a sliver of the Hawaiian island nine miles west of Maui had last set foot there. Now Ellison and his extended family were staying in a new compound above Manele’s steep volcanic shoreline. The cluster of houses was built by Japanese carpenters whom Ellison had once brought in and boarded in private barracks up-island.

For Lanai’s 3,000 regular residents, actually seeing Ellison is rare. His presence is more typically sensed—like a change in air pressure.

“I noticed the salad bar was really good that day,” Shuster tells me. “That’s what it’s like when Larry’s back. People step up. Things just get better.”

For the past 40 years, the people of Lanai have lived at the pleasure of one billionaire or another. Before Ellison there was David Murdock, a real estate magnate who took control of the island in 1985, when it was still a pineapple plantation. Murdock was a visible ruler who’d make his rounds in the local stores, attend community meetings, and give employees he had fired 30 minutes’ notice before sending them off in a helicopter. But Lanai had been a ­money pit for him, and the 2008 crash was the final straw. In 2012, he sold it to Ellison for a reported $300 million.

If Murdock ran the island like the plantation owner he was, Ellison runs it like a distant god. He points, and an amenity appears.

His first move was refurbishing the community pool that Murdock had closed. He answered the housing shortage with the Hokuao development, where the homes are pastel-colored and stamped everywhere with the touch of their benefactor. Each has a Tesla solar roof, a Big Green Egg in the yard, two Japanese Toto toilets, and interiors painted a custom color called Ellison White. (It’s a Benjamin Moore white base with a shot of oxide yellow and a half shot of black, your choice for sheen may vary.) Shuster, who lives in Hokuao, once told Ellison how much he loved the place. “I feel like I moved into your house,” he had said.

“Good,” his host responded. “I wanted to make it like a place that even I could live in.”

Ellison owns Lanai’s only gas station, where a sign reminds customers they’re paying “the Lowest Prices in Hawaii.” And he upgraded the movie theater that today bills itself as being “the crown jewel of theater experiences in Hawai‘i.” In July it was showing Supergirl, which was produced by Warner Bros., the movie studio Ellison, along with his son, will soon control.

“Sigourney Weaver lives here part-time, and she says that this is the most beautiful theater in the world,” Gail Allen, a longtime Lanai resident, tells me. “It serves truffle-oil popcorn,” she adds.

The sense is that life is pretty good on the island since Ellison bought it. Or at least could be worse. “We could have become Molokai,” says Alberta de Jetley, another longtime resident who ran the island’s newspaper, Lanai Today, before selling it to Ellison.

At a picnic table outside Richard’s Market, the other grocery store on Lanai (this one Ellison owns), a handful of residents hold a coffee klatch de Jetley calls the Laugh Group. That morning, beneath overcast skies, the Laugh Group was discussing the island’s recently arrived proprietor.

One member, Mari Lynn Di Lullo, brought up a time she saw a Tesla straddling two stalls in a parking lot. “Jeez, look at the way they parked,” she’d uttered to members of a security detail loitering nearby. “If you didn’t know better, you would think he owned the place.”

Just then the owner of the car—and everything else—appeared, laughing.

“He’s not pretentious,” Di Lullo told her coffee group. “He’s low on the radar.”

The radar. Interesting choice of words about a man who has made a case for a mass AI-enabled surveillance system.

That afternoon a woman came through the grocery checkout line wearing a Sensei Farms sweatshirt. The company is one of Ellison’s island projects: a hydroponic greenhouse concept meant to be the Tesla of agriculture. Eight years in and ­several hundred million dollars later, Sensei Farms describes itself as “a thought ­leader in greenhouse-grown produce.” It has an endcap with boxed salad mixes at the island’s grocery stores.

I introduced myself to the woman and asked what she did for the farm. She smiled.

“They said there would be a journalist on the island today,” the employee told me before starting to walk away. “They warned us about you in our morning meeting.”

I hadn’t told anyone at Sensei Farms I was coming.

Ellison’s newest gift to Lanai is at the entrance to the Four Seasons. In a man-made lagoon surrounded by fake lava rock stands a monumental bronze he commissioned from British artist Damien Hirst. It shows a crew of Polynesian voyagers in an outrigger canoe flung skyward on a cresting wave that up close is revealed to be not water but a knot of sea monsters. A shark bursts through the swell, its mouth open wide enough to take the canoe whole. A mo‘o, the lizard spirit of Hawaiian water, coils below the hull. Amidships, a chief in a feathered cape clutches the ankle of another paddler who is facing away. A loose paddle, some cargo, and a few bronze flowers slide down a wave. And above all of it, from something beneath the surface, hang two giant octopus arms with suckers the size of dinner plates, muscular and curled and about to crash down on everyone.

It’s titled Overcoming Adversity.

PART I: THE CEPHALOPOD

Ellison has long been fixated on the octopus. Cephalopod Corp is what he named the corporate entity atop his private investments. He has another company called Octopus Holdings LP, which, with its general partner Tentacle Corp, put up the money behind Lanai. His venture capital firm that over the years has backed Netsuite, Theranos, and Sensei Farms is called Tako Ventures, tako being the Japanese word for octopus. In many of the villas he built on Lanai hang ukiyo-e prints, many with a tako.

For years it was Ellison’s quiet way to talk about himself.

“His joke is he is the octopus,” says a former executive who worked closely with Ellison. This person was one of several dozen sources I spoke to for this story, most under the condition of anonymity to be able to discuss sensitive matters.

“He loves being the éminence grise. He loves the notion that he’s so powerful, there’s nothing he can’t get into.”

The joke has become a fact in full view. At 82, the last of the founding moguls of Silicon Valley who’s still in the game has extended his grasp into a convergence of power that no other fortune could manage. Where Elon Musk built an empire that’s loud and cultish, Ellison—his mentor and close friend—has pieced together something patient, proximate, and structural. The kind whose shape is clear once you see how far it goes.

One arm of the octopus is wrapped around Oracle, the 49-year-old company he is dragging from dull database vendor into one of the essential data center providers of the AI boom. It is a damn-the-torpedoes move into infrastructure that’s risky even for an executive who nearly lost the company once before. He has saddled Oracle with $130 billion in debt, turned its free cash flow negative, and chained its fortunes to a single volatile partner, OpenAI.

A second arm has closed on American media. Larry’s son David has transformed the independent production company Skydance into the last great consolidator in Hollywood, largely with Dad’s money. Skydance has gobbled up Paramount and with it CBS News; now it has won Warner Bros. Discovery in a $110 billion deal. Ellison also has the American spin-off of TikTok, which an Oracle-led consortium pried loose from its Chinese owner.

A third appendage winds toward political power. As Silicon Valley staged its noisy migration to Trumpism, Ellison worked quietly to influence the president, establishing an effective if not always close relationship. Outside America, he bankrolls his friend Tony Blair’s nonprofit organization, which pushes governments to adopt new technologies like AI. And he has been a steadfast supporter of Benjamin Netanyahu, hosting the prime minister on Lanai while the Israeli leader faced corruption charges at home.

Ellison has had a reputation as a killer in Silicon Valley for decades. In 2011, Bryan Cantrill—who quit Oracle within a year of its taking over Sun Microsystems—told a roomful of engineers not to “anthropomorphize Larry Ellison.” Instead, said Cantrill, think of him as a lawnmower: It doesn’t hate you, it just mows, and if you put your hand in, it’ll chop it off. Cantrill told me recently he hasn’t changed his mind.

But Ellison is partial to the octopus, often deployed as a symbol for power. For Frank Norris it was the Southern Pacific Railroad. In 1904, Puck magazine used it as a stand-in for Standard Oil. In some Nazi propaganda, the head of a Jewish conspiracy appears as an octopus. Dave Eggers used it in his 2013 novel, The Circle, a satire of Silicon Valley, to symbolize tech. It makes sense: The octopus has grasp, it has muscle, it has reach.

“That is a lot of media to be owned by one family, especially a family that has made tens of millions of dollars in donations to Trump and other right-wing organizations,” Senator Bernie Sanders tells VF. “When we talk about oligarchy, it is absolutely imperative that we focus and spend a lot of time looking at who owns the media and what their goals are.”

Ellison has become a significant GOP donor, including a $45 million gift to a pro-Trump nonprofit in 2024, according to The Wall Street Journal. But if you’re looking for a network of influence in the vein of a Koch or a Soros, you’re going to come up empty. Beyond Israel, it’s hard to tell whether there is a larger Ellison political project.

A friend insists to me that, despite all the evidence, Ellison is nonpartisan: “Larry just loves you or he doesn’t.” OpenAI’s head of policy, Chris Lehane—a former fixer for Bill Clinton who now works closely on the joint Oracle data center project—observes that the titan prefers operating from a higher vantage point. “Larry is on Mount Olympus, throwing thunderbolts,” he says. “It’s how he’s always operated.”

But Zeus never had to deal with the inconvenience of mortality. Ellison’s desire to build an empire in his ninth decade has a sense of urgency—a lifetime spent enjoying extravagant success, yet now searching for something else.

“I don’t think he sees himself as a small figure in history,” says one former Oracle executive. Ellison, a big reader of biographies, has told colleagues and friends he models himself after Winston Churchill and Napoleon—a political project if ever there was one. “He aspires to and would like to see himself as a world historical figure,” the former executive adds.

The image-conscious billionaire has fought aging to a draw. Decades ago, he stared out handsome and confident from the cover of biographies and business magazines. Since then his face has both leaned out and puffed up in the way that tends to happen with the very rich. His eyebrows, never much to speak of, have faded to mere suggestions. He remains active and trim, his beard impeccably groomed. When Ellison talks, his voice is startlingly young.

Yet death informs much of this latest chapter. Cancer has claimed his closest friends and family members, including his adoptive mother, his Oracle cofounder Bob Miner, its former co-CEO Mark Hurd, Steve Jobs, and even a beloved cat, Maggie. The losses have fed an obsession with wellness and sent billions of his fortune toward new approaches to fighting the disease.

“He’s lost too many people in life, and it’s impacted him,” says one of Ellison’s longtime friends. “Jobs’s death shocked Larry. But eventually we all come to terms with mortality.”

PART II: THE HEAD

The story of Ellison’s early years—born to an unwed mother, raised by a great-aunt and uncle in South Chicago, twice a college dropout before he lit out for California—has hardened into Silicon Valley legend.

After moving to the Bay Area, he drifted for a bit. His adoptive father told him he’d never amount to anything, and Adda Quinn, his first wife of an eventual six, informed him that he “lacked ambition.” In the evenings, Ellison and a college friend who’d followed him west would look out at the city and pick out the apartment buildings they’d buy once they had money. They talked about the company they’d someday start, which Ellison unsubtly named Universal Titanic Octopus.

As a self-taught programmer, he worked his way into a tech scene that included Jobs, Steve Wozniak, and Bill Gates. Ellison’s interests were more structural than his peers’ and, frankly, boring. In the ’70s, he was taken by the newish concept of a relational database—a way of organizing information so any part of it could be connected to any other.

Every company on earth would soon have more information than it could keep track of. Governments too. Ellison and his cofounders would sell them the software to make sense of it.

The software executive made up for any dullness of mission by becoming a bombastic media figure and maniacally competitive salesman. Through the ’80s and ’90s, he publicly jousted with peers, especially Gates. “The thing I find most contemptible is Bill’s lying. This thing about innovating—it makes me want to puke,” Ellison said in a 1998 talk at Harvard. “Microsoft has innovated nothing.” Over time the rivalry lost its edge. When Ellison bought the Indian Wells tennis tournament in 2009, he would frequently share his owner’s box with Gates and Hurd and his wife, Paula. After Hurd had passed and Gates divorced, Paula and Bill became an item.

The business press couldn’t resist the image of Silicon Valley’s swashbuckling technologist who moonlit as a daredevil. And Ellison gladly provided the material. He flew an Italian fighter jet, collected sports cars and speeding tickets, and surfed until a wave almost broke his neck. Ellison’s obsession with yacht racing was all-consuming. He took months away from Oracle to chase sailing’s biggest trophies.

It all nearly ended in 1998 during the ­Sydney-to-Hobart open ocean race when the boats went into a hurricane on the second day in, shredding sails. Of the 115 yachts that started, only 44 finished; six sailors died, one from a heart attack. Ellison pushed through and reached the finish line hours before the next competitor. (Among his crew on the maxi Sayonara was a 27-year-old Lachlan Murdoch.) The race rattled him—enough to make him drop his daredevil persona. “It wasn’t Mother Nature’s worst,” an emotional Ellison told an Australian TV ­interviewer after the race. “Had it been, she would have killed us.”

He spent the next 17 years chasing the America’s Cup, a race that took place in the relative safety of coastal waters. He won back-to-back cups in 2010 and 2013, the first as BMW Oracle Racing, the second as Oracle Team USA. His wins never brought him acceptance among the sport’s Waspy enclave of Ivy grads; he raced with the modestly outfitted Golden Gate Yacht Club. “It was like an organ rejection,” says one person in the yacht-racing community.

Still, traveling with his America’s Cup team, he enjoyed the big crew dinners of rambunctious sailors, joining them as they sang Frank Sinatra songs into the night.

“We worked for him in a part of his life where he didn’t feel the need to be the strong, single-minded leader that he was at Oracle,” says a longtime member of his team. “He was starting to get really wealthy, and life stopped being normal. We were a bit of normalcy.”

Eventually he broke with the Cup and cofounded a rival league, SailGP, which raced volatile foiling catamarans. His goal was to bury the America’s Cup and grow SailGP into the Formula 1 of boat racing, as several sources put it.

Yet still Ellison turns up to the America’s Cup, if just to observe. A visitor who joined Ellison from his boat at one race remarked to VF about how solitary a figure the billionaire spectator cut: “It was one of these great tragedies as he watched it happen. It’s a recognition of how the Cup would never take him.”

PART III: THE MACHINE

In the 2000s, Oracle was a company facing stagnation. The core database business remained profitable, but the dot-com crash was humbling.

Through much of this stretch, Oracle’s stock went sideways, propped up by the company’s relentless repurchasing of its own shares. Ellison simply held on, and as Oracle’s total share count shrank by roughly half, his slice of the company grew from around 23 percent in the early 2010s to north of 40 percent by 2025. At the time the company’s stock was idling, Ellison was gaining total control.

“It’s essentially a private-public company,” says Brad Reback, a longtime Oracle analyst with Stifel. “Once you take the passive investors in the stock into account, there’s nobody to challenge him.”

Initially Oracle sat out the 2010s cloud computing revolution, which Ellison spent years dismissing as “complete gibberish.” When Amazon, Google, and Microsoft emerged as giants of the burgeoning space and began encroaching on Oracle’s database products, he was convinced to come around. In 2014, Ellison turned 70 and slid over to focus on Oracle’s core products as its chief technical officer, splitting the CEO role between Hurd and Safra Catz, the company’s CFO, known for being sharp and conservative.

Then the AI boom came along, giving the languid software giant a chance to reinvent itself. Ellison had a solid relationship with Nvidia and its leader, Jensen Huang, who gave Oracle a line on the chip ­designer’s invaluable silicon. The company went headfirst into building AI data centers, with Nvidia and xAI—his buddy Musk’s AI start-up—its anchor tenants.

On September 9, 2025, Catz announced during Oracle’s earnings call that it had signed contracts with several unnamed customers during the last quarter, adding up to $317 billion in future data center billings. News of the sudden windfall sent an overheated AI market into a frenzy. The next day Oracle’s stock shot up more than 43 percent, the biggest one-day gain since 1992. For a moment during that trading day, Ellison surpassed Musk as the richest person in the world. The truth, as revealed by The Wall Street Journal, was that $300 billion of those billings could be traced to a single customer: OpenAI.

The two companies had been circling each other for months. Back in January, on Donald Trump’s first full day in office, Ellison stood in the White House beside the president, OpenAI’s Sam Altman, and SoftBank’s Masayoshi Son to announce a data center joint venture called Stargate.

Trump beamed at the three executives as they laid out their vision of a $500 billion project. At the podium, Ellison boasted that construction was already underway on a massive Oracle-OpenAI data center in Abilene, Texas. Not everyone was prepared for the Abilene mention. Some of the companies building the site didn’t know they were working on Stargate at all until they heard Ellison say it.

Then a question that began as a murmur among investors and employees grew into the only one that mattered: How, exactly, was Oracle going to pay for tens of billions of dollars in Nvidia chips?

At the Abilene site—a wind-scorched plain 180 miles west of Dallas—Oracle employees turned the question into a punch line. They’d look at each other and shrug. “Don’t worry. Uncle Larry will pay for it.”

But unlike Amazon, Google, and the other cloud giants that are otherwise ­money machines, Uncle Larry did not have the cash. Instead Oracle turned to debt, and in a terrifying way. In its last fiscal year, the company raised $43 billion through bond offerings, pushing total borrowings toward $130 billion. Capital expenditures more than doubled, and its long-healthy free cash flow cratered to -$23.7 billion.

The deeper the red on the balance sheet, the more uneasy the bondholders grew. In July, S&P cut the company’s credit rating to a notch above junk. Lenders started to balk at some Oracle projects; the company backed out of a planned expansion of the Abilene campus. In September, it sent a force majeure notice on its New Mexico site, seeking to defer payments if the project slips, though Oracle insists it's on schedule. Some loans tied to the project now trade around 90 cents on the dollar, the Financial Times reported.

Mounting worries caused the company’s stock to give back all its gains—and then some. Since peak, Oracle shares have fallen by more than half; Ellison’s own net worth has dropped some $200 billion, from a high of $400 billion to about $217 billion in September.

“Ellison has really put it all on red,” says John Hempton of Bronte Capital, a global hedge fund. “I can’t tell if he did it because he’s a gambling man or out of weakness.”

On the inside, the hidebound Oracle was coming to terms with its new, leveraged self. Since joining a decade after the company’s ’90s financial scandal, Catz had seen her job partly as helping Ellison realize his vision, but also as tamping down on the more destructive impulses within the company. She was adroit at breaking through to the cofounder. “I know how to speak Larry,” Catz told one associate.

But speaking Larry has its limits. Former executives say Catz never loved Oracle’s lower-margin infrastructure business, and now it was taking over on the backs of a small number of AI clients. The company needed someone who came from that world, and Ellison threw in with the president of Oracle’s cloud team, Clay Magouyrk, who was named co-CEO in September 2025 along with Mike Sicilia, who leads Oracle software. Catz stepped down, though she stayed on as vice-chair of the board.

Many leaders in the tech industry have looked at how much the company has borrowed with an amused sense of awe. “Imagine if you put in all that capex and it all fizzles out?” wondered one former Oracle executive. But the optimistic case is simpler than it looks: It would take OpenAI going to zero for Oracle’s data center bet to fully blow up. And Oracle is already touting returns, boasting that OpenAI’s latest model, Astra, was trained in Abilene.

“Go back to last year and everyone thought Sam was certifiable with how much capacity it would take to run AI,” says Stifel analyst Reback. “But at this point, to some extent, OpenAI is too big to fail.”

PART IV: THE SON

Like many billionaires, Ellison had run his financial life on a single trick: Never sell the stock; borrow against it instead. According to the company’s 2026 proxy, he’s the only Oracle employee allowed to use his holdings to take out personal loans.

Ellison’s spending habits and refusal to sell his Oracle shares have alarmed his own advisers. In emails surfaced in 2006 from a recently settled shareholder suit, the head of his family office, Philip Simon, begged him to rein things in—or at least offload some stock. Ellison’s planned spending had included $194 million for a new yacht, $80 million for his America’s Cup racing team, and $20 million for “lifestyle.”

“I’m worried, Larry,” Simon wrote in a 2002 email. “It’s imperative that we start to budget and plan.” The accountant later testified in a deposition that he told his boss “we have a freight train going down a track hitting a debt wall.”

Simon, who later retired as the head of the family office, once admitted to a colleague that he’d grown tired of being Ellison’s buzzkill. He said that his replacement in the job, Paul Marinelli, was more willing to let Ellison have fun, Simon told the colleague. (Simon did not respond to Vanity Fair.)

As Oracle laid out in the 2026 proxy, more than a third of Ellison’s stake—413 million shares, up 19 percent from the previous year—was pledged as collateral against personal loans. “Personal,” in Ellison’s later years, had come to include his children.

To date, Ellison has been married six times: to Quinn and then Nancy Wheeler in the broke California years; to Barbara Boothe and then Melanie Craft as Oracle grew into a giant; and to Nikita Kahn and then Jolin Zhu in his latest chapter. He has children with only Boothe and Zhu.

Ellison’s three years with Boothe, Oracle’s onetime receptionist, ended acrimoniously with a fight over their prenuptial agreement. In the divorce, Boothe won custody of David, born in 1983, and Megan, born three years after that. He played only a small role in their upbringing and later told friends he regretted being absent in their early years and always on the go. “The children turned into great kids because of their mother,” Ellison once said to a close associate.

He was around more as they got older, and when they pursued careers in Hollywood, Ellison set them up with Ken Ziffren and Skip Brittenham of the powerhouse entertainment law firm Ziffren Brittenham to act as business advisers. But each child would pursue a different path.

In 2011, Megan used a share of the family fortune to launch the production company Annapurna Pictures with the goal of taking on difficult, artistically minded movies. The company had a celebrated early run that included The Master, Zero Dark Thirty, and American Hustle.

She told employees and investors that she wanted to run Annapurna as a real business and not simply play the role of Hollywood Medici, but the economics of creating art were brutal. Megan’s inexperience and willingness to greenlight movies with unrecoupable budgets didn’t help, say people close to the company. When cash grew tight, as it did more than once, Megan would trek to Malibu or Indian Wells or the Bay Area—wherever her father was at the time—to ask him for money, one former executive recalls.

In 2019, after a string of flops and a disastrous gamble to become a movie distributor, Annapurna’s creditors and lenders were calling. Ellison stepped in, buying out the company’s debt at roughly 80 cents on the dollar, says someone who was briefed on the negotiations. It saved Megan the embarrassment of the banks foreclosing on Annapurna, but the company has never fully recovered as a major film and TV house.

In the wake of Annapurna’s crisis, Megan would disappear, often to Lanai, where relations between father and daughter appeared frosty. The two avoided eye contact at the Four Seasons tennis courts, one observer noted.

David took more after his father, sharing his commercial instincts and adrenaline-fueled hobbies. His production company, Skydance, named for the sport of stunt flying, made big-budget action movies rather than Oscar bait. The company landed a number of early hits like Star Trek films and the later entries in the Mission: Impossible series. Ellison would often speak glowingly to friends and associates about his son’s successes. “Larry is 150 percent behind his son, who may be an even smarter and better businessman than he is,” says Salesforce CEO Marc Benioff, a former Oracle executive and longtime friend.

Making hit movies wasn’t enough for David, who wanted an empire of his own. In late 2023 he made a move on Shari Redstone’s media firm Paramount Global, which was struggling and looking for a buyer. The next spring David beat out rival bidders with an $8 billion package co­financed by the private equity firm RedBird Capital and some $6 billion from his father.

During the negotiations, David made clear to all parties that while Larry was the largest backer of the deal, he was the one in charge. He invoked his father just a handful of times in negotiations and rarely by name. Once, during a discussion about a payment schedule, he cut in to say that he needed to check in with “a principal,” says one person involved in the discussions. It seemed clear to everyone whom David meant.

Not long after the Paramount deal closed in the fall of 2025, news began leaking to the business press that the new Paramount Skydance was preparing a bid for Warner Bros. Discovery. David Zaslav’s conglomerate had already announced a plan to split itself in two, separating the studio and streaming assets from its cable channels like CNN. David Ellison’s plan, again with his father’s support, was to buy the whole thing. But that December, Netflix swooped in with an offer to buy just the studio and streaming assets for roughly $83 billion. The WBD board, seeing Netflix as the cleaner deal, picked it.

The Ellisons were undeterred. Getting WBD would now mean raising the price and executing a costly hostile takeover. But the major backers of the deal, Gulf State sovereign wealth funds, weren’t going to increase the $24 billion they’d already committed.

That put pressure on the Ellisons to step up even more. Paramount Skydance increased its offer by a dollar a share over Netflix—pushing the total to $110 billion in enterprise value—and the WBD board insisted that Larry also issue a $40 billion guarantee backed by his Oracle holdings. He did, and on February 26 Netflix walked. The next day, the WBD board elected to go with Paramount Skydance. In September, Paramount Skydance settled with a dozen state attorneys general who had sued to block the merger, agreeing to concessions including guardrails on CNN—and clearing the last hurdle to closing.

As the price went up and the merger grew more bitter and political, people close to Ellison wondered why he went in on his son’s media adventurism at all. Unlike his friend Steve Jobs, who cofounded Pixar and grew close to Disney’s Bob Iger, Ellison has never had much use for the media business. Years ago, when Netanyahu tried to get him to buy an Israeli newspaper owned by one of the prime minister’s rivals, Ellison declined. He later told investigators examining the meeting, which surfaced in Netanyahu’s corruption trial, that his answer was straightforward: “This isn’t my business. I am not in the newspaper business.”

A theory floated by a friend is that with Paramount and especially WBD, Ellison is energized by the battle itself. Like yacht racing and data centers, it’s yet another arena of competition.

“Once he engages, he has to win,” the friend says. Then there’s the opportunity to support his children. The man who was ­given up by his mother and played only a minor role in David’s and Megan’s upbringing is trying to make good.

“I wouldn’t be at all surprised if he’s uncomfortable with it but convinced it’s all okay because it’s David,” says a former executive who worked for Ellison. “David is the golden child.”

PART V: THE OFFICE

When young Ellison looked out at San Francisco in the late ’60s and dreamed of owning buildings, he was seeking only a piece of the city. What he ended up collecting extended much further. Dubbed a “landmaxxer” by The Wall Street Journal, Ellison has collected properties in Hawaii, California, Rhode Island, Nevada, Japan, and, increasingly, Florida.

Most of his Florida holdings are in and around the barrier island town of Manalapan. The haul includes a record-setting $173 million 16-acre oceanfront compound and the $277 million Eau Palm Beach Resort & Spa. The luxury resort comes with a private beach and access to a 42,000-square-foot spa and is a 20-minute drive to Mar-a-Lago.

For the onetime Democratic donor, getting to 20 minutes from Trump has been a decades-long journey. In the ’90s Ellison was an avid supporter of California congressman Tom Lantos, with whom he maintained a close friendship until his death in 2008. He gave generously to Bill Clinton while he was president, privately calling him the “best politician of my lifetime.”

Asked to define his politics in a 2018 Fox Business interview, Ellison ran through where his favored leaders stood: “Bill Clinton was a centrist. Tony Blair was a centrist. Marco Rubio is a centrist. Mitt Romney is a centrist. Those are my politics.”

The extremist in his view is Barack Obama, who he privately said turned him against the party. Ellison griped to an executive that he once held a briefing with Obama, who was barely listening to him. The chief sin, though, was his administration’s stance on Israel, which Ellison saw as ­insufficiently supportive. He was incensed by the Iran nuclear deal, one associate says.

Ellison has shifted even further right in recent years as he grew closer to Musk. He invested $1 billion in the acquisition of Twitter, which he told people was the only reliable source of news. And he shares Musk’s fears of so-called wokeness. Cancel culture, he once told a friend, is the reincarnation of Robespierre’s reign of terror.

But he was late in backing Trump. Ellison supported Rubio in the 2016 GOP primary. After Trump won, Jared Kushner convened a gathering of top technology executives at Trump Tower—but it was Catz, not Ellison, who attended.

“We went through that list a thousand times. His name never came up. That tells you all you need to know,” one former Trump adviser recalls.

In February 2020, as the COVID-19 pandemic set in, Ellison hosted a campaign fundraiser for Trump at his estate near Palm Springs. Ellison did not attend and brushed it off as not an endorsement but a patriotic duty to support whoever holds the office.

There was more to it than he let on. Ellison was in contact with Trump during that time and offered Oracle’s software to federal agencies as a way to track the disease’s spread. He also discussed launching a federal program to evaluate different treatments for COVID. The idea could be traced back to David Agus, the Los Angeles physician and Ellison business partner who runs the Ellison Medical Institute at USC.

Ellison’s inching proximity to the president accelerated months later when a new prize came on the table: TikTok.

In 2020, as the first Trump administration moved to force a sale of the app on national security grounds, Oracle emerged as a candidate. After a call with Ellison and Walmart CEO Doug McMillon, who was partnering on the bid, Trump told reporters that Oracle would be a good suitor and that the deal would include a $5 billion fund for patriotic education of American youths. That deal fell apart on both the US and Chinese sides, and TikTok’s fate remained in limbo under Joe Biden.

During Trump’s second term, Oracle was once again in the running for a stake in the company. At the Stargate press conference, a reporter asked the president whether he’d support Musk buying it.

“I’d like Larry to buy it too,” Trump responded, then suggested that half the company go to the United States and half to a private buyer. He turned to Ellison—“What do you think?”

“Sounds like a good deal to me, Mr. President,” Ellison said.

“He can afford it too,” Trump added.

This time it went through. Oracle’s real win was operational: It would host TikTok’s US user data in its cloud and oversee security of the prized algorithm.

The day after the deal was certified, Netanyahu spoke to a private gathering of pro-Israel influencers. “We have to fight with the weapons that apply to the battlefield with which we are engaged. And the most important ones are on social media,” he told the group. “The most important one going on right now is? TikTok. TikTok. Number one.”

There’s no evidence Ellison was in touch with Netanyahu about the TikTok deal. But the executive’s commitment to Israel, and to the prime minister, runs deep.

Friends who knew Ellison as a casual supporter of Israel have been surprised to watch him become one of its most consequential allies. He was raised in a largely secular Jewish household and his children weren’t brought up in the religion at all, one associate says.

Ellison’s first trip to the country only came in 2007, with his then wife Melanie Craft and 12 family members. Along with the country’s foreign minister, they toured the town of Sderot near the Gaza border and Ellison spontaneously pledged half a million dollars to fortify a community center against rocket fire, promising the money would arrive the next day. Ten years later, Ellison made a $16.6 million donation to the Friends of the IDF, a charity that funds soldier welfare. It was the largest gift in the charity’s history.

Catz and Ellison have privately boasted about Oracle serving the Israeli government and the IDF as clients. In conversations with Oracle executives, Catz has likened herself to a celebrity in the country, says a source.

Influence has run the other way as well. At Netanyahu’s urging, the Sensei Farms team hired an Israeli firm to design the greenhouses for the farming project, but it didn’t go well. The structures were built for the desert and Lanai’s trade winds blew the plastic roofs off, repeatedly.

In late 2021, Ellison hosted the Netanyahus at one of his Lanai villas while the out-of-office prime minister faced a corruption investigation in Israel. As Ellison’s guest, Netanyahu and his wife sat at the owner’s table at Nobu, where they ordered smoothies. That same year Ellison also reportedly offered him a seat on Oracle’s board, which came with a $450,000-a-year salary and stock options. Netanyahu is not on Oracle’s board, and he has denied the report.

In 2015, as Ellison weighed whether to back Rubio, he met with the candidate to test his commitment to Israel. “I’ll tell you how dinner goes,” Ellison wrote to a top Israeli diplomat in a hacked email later published by Drop Site News. After the meal, Ellison relayed that the candidate passed: “Marco will be a great friend for Israel.”

He also wrote that he’d be introducing Rubio to Tony Blair.

If Ellison’s bond with Netanyahu is ideological and personal, his relationship with Blair falls somewhere between a friendship and a business-­advancing charity. Blair often was a guest on Lanai, where Ellison once gave him a tour of the Sensei greenhouses and offered him some tomatoes off the vine that he said were organic. (In fact they had been sprayed with chemicals, which prompted a greenhouse worker to urgently stop Blair before he took a bite.)

Ellison is by a wide margin the dominant funder of the Tony Blair Institute for Global Change, a think tank that embeds advisers into world governments and pushes for techno-optimist reforms. In 2023, more than 97 percent of the Ellison Foundation’s charitable giving—roughly $52.5 million—went to Blair’s institute. In 2024, all of the donations, about $70 million, went to the institute, according to tax filings. In both years it cited the purpose of the donation to be “to support effective governance work in Africa.”

The people who worked around Ellison saw the logic plainly. The former prime minster’s credibility could open doors that a pitch from an American software comp­any never would.

“For Larry, the relationship was expedient. Tony was an effective ambassador and a way to gain influence in markets and geographies,” says an executive who worked with Ellison. “How else do you go into a country in Africa and convince them to use some clinical software?”

VI. THE PRIVATE MAN

In a September 2023 speech at the Oracle CloudWorld conference in Las Vegas, Ellison paced the stage in a black long-sleeve tee and laid out the stakes for the company’s work in health care. The year before, it had completed its biggest ever deal: a $28 billion acquisition of health-records giant Cerner. “I’m not sure there’s anything we’re working on here at Oracle that’s more important than this,” he told the audience at the Venetian.

It was never only a business proposition. Ellison has told friends and colleagues that fixing a broken health-records industry and helping find cures is the legacy he wants.

He was devastated by Jobs’s death, people close to him say. What haunted him was how avoidable it was. Jobs had been diagnosed with a rare treatable form of pancreatic cancer, and Ellison was exasperated by the Apple CEO spending months trying to cure it with a diet of fruit juices and plant nutrients.

“Larry was like, ‘Macrobiotic diet my ass,’ ” says one friend. “It was an unnecessary loss.”

His conviction that it would take someone bold to fix health care had already led him to Elizabeth Holmes. Ellison invested in Theranos through multiple vehicles, and even after the company collapsed and she was charged with fraud, he still defended her. He told a former colleague that he thought Holmes was “a genius.”

Another associate believed that Ellison was “smitten” and noted that he talked about Holmes with a twinkle in his eye, describing her as destined to change the world. “I think he absolutely believed that,” this associate said.

The billionaire has entrusted many of his private wellness initiatives to Agus, who treated Jobs during his cancer battle. How effective the money has been in advancing cancer therapies is unclear. Agus has maintained that Ellison is unconcerned by the level of investment and said in a Los Angeles Times story that Ellison had told him “money doesn’t mean that much to me.”

Perhaps. Over the years, Ellison has grown skeptical of traditional philanthropy, believing his bets should make money. In 2024, he shut down Project Ronin, a cancer-focused software start-up he cofounded with Agus that had raised $35 million.

The math on these endeavors has been tricky. Ellison has bragged to colleagues about his closeness to Musk. “I think Elon is my best friend. And I think I’m his best friend. He’s made me $3 billion,” Ellison once said to a group of people, according to a person present. He has grumbled that Agus, in contrast, has cost him a lot of ­money.

A person close to Agus said this has been an ongoing joke that Ellison has made in front of Agus and others.

As the octopus arms have extended into everything, the head has receded more from view. Once a fixture of business-magazine profiles, Ellison is now rarely seen or heard from outside regular Oracle events. In June he was absent from Oracle’s earnings call for the first time in years. (Before that, the last time he skipped was in 2013 to watch the America’s Cup.) He did not respond to multiple requests for an interview with VF.

The withdrawal is fitting for a man who crafted a playboy image but never settled into it. A friend described him as more of a homebody—“monastic in a business suit.”

That didn’t mean passionless. Ellison’s self-description is of someone who experiences an all-consuming attraction to another person that, sooner or later, taps out. “I’m always deeply in love with the person I’m with until I’m not,” he once told a colleague.

The string of marriages bears that out. Ellison and Quinn lasted seven years, and she later told a biographer, “by the time I left, I was worn out.”

His second, to Wheeler, was a blip in the late ’70s. In the divorce, Wheeler sold her stake in the company that would become Oracle to Ellison for $500—holdings that today would be worth billions.

Next came Boothe. Despite the messiness, they remain friends and she told a biographer that she never wanted to marry again—or even date seriously—after Ellison. Anyone else would be unexciting.

In 2003, he married Craft, a romance novelist, after dating for eight years. Jobs was the wedding photographer. While they were together, Craft published a novel, Man Trouble, about a history professor turned romance novelist who falls for a billionaire tycoon. She said it was only partially based on Ellison. Then came Nikita Kahn, a Ukrainian model. They divorced in 2020.

Between all of that—and sometimes during—were the girlfriends. During an Oprah appearance Ellison said that he hadn’t found the right woman yet, which, after the episode aired, set off a flurry of applicants vying for the job. His Dionysian image is complicated, though; Ellison has been a teetotaler for years and swore off alcohol in his 20s after he drunkenly hit on a friend’s fiancée, he told a biographer.

His habit of dating Oracle employees was well-known inside the company. In the ’90s, a relationship with an administrative assistant, Adelyn Lee, ended badly and she sued for sexual harassment and wrongful termination. Oracle reportedly settled for $100,000, though she was later convicted for forging documents in the suit. Handling the money around all the dalliances fell to the family office. Philip Simon sighed to a colleague once that this was his least favorite part of the job at Cephalopod Corp.

These days Ellison spends his time at his Florida compound or in Oxford, England, where he and Zhu are raising their five young children. How Ellison met his sixth wife is a mystery to people who know him. One version he has told is they met on a trip to Japan, where she’d gone to boarding school. Another version was they met while he was touring the University of Michigan, where she was a graduate student. One friend’s understanding is they met online.

She’s been to some Oracle-sponsored events and was photographed with him at Indian Wells. In 2024, the couple made a large donation to the University of Michigan’s booster group, which used the money to recruit a star quarterback. In a press release, the group thanked “Jolin and Larry Ellison,” though it later pulled it down and rewrote it as “Larry and his wife Jolin.”

Their age difference—she’s 47 years younger—is something Ellison has been defensive about in private. “She’s not some poor little Chinese girl I picked up somewhere,” he once told someone unprompted.

On Lanai, the gestures Ellison made for Zhu and their family spilled into island daily life. Some were practical: He built a Montessori school for their children and made it broadly available—for a price.

Others were more on a whim: When he renovated the island’s oldest inn, the Hotel Lanai, he installed an outpost of the Chinese restaurant Chengdu Taste for her. The locals hated it. After the Ellisons left for Oxford, Chengdu Taste quietly closed and Larry later brought in a well-known Los Angeles burger chef to redo it as a bar and grill.

During the pandemic, when the Ellisons lived for an extended stretch on the island, he threw himself a birthday party and flew in his A-list guests. Jeff Bezos landed his helicopter on the golf course in Manele; Blair and Netanyahu were there too. But Zhu told someone that she wasn’t going, saying she was too much of an introvert.

Ellison’s staffers were repeatedly told not to walk the golf course at dusk because Zhu would be wandering there with her children.

People who worked for Ellison—people who, for the record, like him—keep circling the same paradox. With an audience, he could be brash and dominating and insistent on holding court. One-on-one, he softened into curious, good company. But his friendships often have the quality of a summons, people who’ve been around him say. He does not simply have people hanging around; he assembles them, flies them in, keeps a cast. Afterward, he recedes.

“There’s something tender and sad about it. I think he lives a performative life,” observes another person who worked with Ellison for years at Oracle. “He’s like a Hollywood star who knows 10,000 people and is completely alone.”

EPILOGUE: OVERCOMING ADVERSITY

A couple of years ago, Shuster walked into the bar and grill at Hotel Lanai where he spotted Ellison along with David and Agus at a table. The doctor beckoned him over and they all chatted for a bit.

Shuster got a sense that Ellison’s son seemed anxious that their dinner had been interrupted. The pharmacist put it together later: The evening fell a few weeks before the Paramount deal was announced, and David was probably hoping to keep talking shop with his dad.

But Ellison was excited. He asked Agus to pull out his phone and show Shuster early models of Overcoming Adversity, the Hirst statue for the Four Seasons.

“He showed me a picture of a mock-up—all silver—of something I couldn’t distinguish what it was,” Shuster says. “And I was shocked, like, what is this?”

After the sculpture was unveiled last December, Lanai Today posted pictures of it on Instagram. Instead of focusing on the bestiary, the newspaper highlighted a smaller feature beneath the main action: a turtle that’s swimming below the chaos. “Perhaps the best way to overcome adversity is to not engage in it at all,” the post said.

In the comments, Shuster’s wife wrote that the cultural background someone brings to an artwork is what determines its meaning. “As a Japanese viewer, I personally associate the turtle with an existence that does not deny death, but rather dissolves into the flow of time itself.”

In the afternoon, I caught a ride with Lanai’s only shuttle service to make the last ferry back to Maui. My driver, Amelia, was third-generation Lanai—her grandparents had worked on the pineapple plantations. Amelia then worked for a time in construction for the island’s management company until that whole division was laid off. Hence why she was now a shuttle driver.

As we took the turn past the Manele Four Seasons and headed down the winding road to the harbor, Amelia cut her story off and casually gestured out the window.

“So, what did you think of the Kraken?”