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.
by Tom Dotan, Vanity Fair | Read more:
Images: Yuko Shimizu; Damien Hurst
[ed. Vicious and evil.]


