By Tyler Sonnemaker
November 20, 2021
In 2014, Mark Zuckerberg bought more than 750 acres in a region of Kauaʻi called Koʻolau.
But the privacy-obsessed Facebook cofounder had a problem: His properties surrounded dozens of small parcels of “kuleana” land.
These parcels, originally created to preserve land for Kānaka Maoli [Native Hawaiians], were co-owned by hundreds of Kānaka Maoli and kamaʻāina [Hawaiʻi-born residents].
Over the next few years, Zuckerberg used shell companies to quietly acquire all but four kuleana parcels.
In 2016, after several co-owners refused to sell, Zuckerberg and another co-owner, Carlos Andrade, sued for the remaining land.
Zuckerberg quickly backed out amid public outcry over his “quiet title and partition” lawsuits, a type of legal action that has “long been exploited to forcibly sever Native Hawaiian families’ connections to their ancestral lands,” according to the state’s Office of Hawaiian Affairs.
But Zuckerberg’s coplaintiff, Andrade, pressed on, and acquired the parcels for $2.1 million by prevailing in a court-ordered auction with a bid that other co-owners have accused Zuckerberg of secretly financing. (Ben LaBolt, a spokesperson for the Chan Zuckerberg family office, declined to comment on the allegations of secret funding but said Zuckerberg does not own the four parcels).
Zuckerberg isn’t the first outsider to use money or power to snatch up large tracts of Hawaiian land, and he likely won’t be the last.
The modern history of Hawaiʻi is founded on land appropriation. In 1893, American businessmen, mostly from the plantation industry, overthrew the Hawaiian Kingdom’s government, seizing ownership of 1.8 million acres of public and private land as well as control over the country. Five years later, they “ceded” those lands to the US, which came to rule Hawaiʻi through an annexation process some legal experts argue violated both the US Constitution and international law.
Today, the heirs of plantation owners and overthrow conspirators still own at least 300,000 acres of land throughout Hawaiʻi. They’ve also sold more than 150,000 acres to tech billionaires, including 89,000 acres to the Oracle cofounder Larry Ellison and 38,000 acres to the AOL cofounder Steve Case.
Kānaka Maoli, meanwhile, disproportionately experience homelessness, poverty, and food insecurity. The US government’s promises of land reparations have largely languished.
Nearly half of all Native Hawaiians have left Hawaiʻi as the median home price surpasses $1 million, exacerbated by nonresidents, including many Silicon Valley elites, buying second homes and properties to convert into vacation rentals.
Zuckerberg’s real-estate purchases on Kauaʻi have all been legal and, in many ways, consistent with the extravagant lifestyle of other jet-setting billionaires. As a result, the extensive local backlash to his expanding estate — now totaling 1,382 acres, or roughly 1,050 football fields — may surprise those unfamiliar with Hawaiian history.
To better understand why Zuckerberg sparked so much controversy, I delved into the roots of the land he now owns, consulting Hawaiian historians, legal experts, activists, politicians, and several of Zuckerberg’s Kānaka Maoli neighbors, as well as countless historical sources. I discovered that his properties reflect just how much Hawaiian land has been appropriated and the myriad ways in which it was taken — some blatantly illegal, and others, as with Zuckerberg’s acquisitions, insidious but legal.
In March, Zuckerberg paid $53 million to add nearly 600 acres to his Kauaʻi domain, buying land whose previous owners played a key role in the overthrow of the Hawaiian Kingdom.
LaBolt, the spokesperson, told Insider that Zuckerberg and Chan have made various contributions to the local community, adding that “the vast majority” of the couple’s land is “dedicated to sustainable farming and ranching operations, with a commitment to agriculture and conservation practices overall.”
But many Kānaka Maoli also told me that Zuckerberg’s sprawling Kauaʻi estate reflected a fundamental difference in values between Hawaiians — whose traditional land-use system prioritized sharing, cooperation, and sustainability — and those in control of Hawaiʻi since the Kingdom’s overthrow.
“Americans put down monarchies, yet they’ve created kings themselves and they’re called billionaires. They may not call them kings or monarchs, but they have total control over the land,” Randy Naukana Rego, a Kanaka Maoli whose family once owned about a quarter of Zuckerberg’s land, told Insider.
“This is the new monarchy.”
Zuckerberg’s estate already boasts multiple stunning, several-thousand-square-foot homes.
But on a bluff overlooking the ocean — where illegal alterations netted the previous owner, the car dealer Jimmy Pflueger, a $7.5 million fine from the Environmental Protection Agency — Zuckerberg has stripped the land bare to make way for his pièce de résistance.
The concrete foundations don’t reveal much at this point, but county building permits describe a palatial $23.7 million, 57,000-square-foot main residence with 17 bathrooms, a $2.8 million swimming-pool complex with hot tub and ice bath, a $40,000 barbeque pit, and two 28,000-square-foot “recreational” buildings, among others.
The cluster of buildings and structures, valued at roughly $95 million, are expected to have a combined footprint of 178,000 square feet — the equivalent of nearly 100 typical homes on Kauaʻi but still less than 1% of Zuckerberg’s land on the island.
Zuckerberg’s estate, which he named Koʻolau Ranch, is a patchwork of properties acquired over seven years that reflects many of the ways Hawaiians have lost land to foreigners.
The 592 acres Zuckerberg purchased in March came from the heirs of plantation owners involved in the overthrow of the Hawaiian Kingdom. In 2014, he bought 364 acres that had been taken from a Hawaiian chief’s wife in a controversial court case a century earlier, and included kuleana lands acquired through lawsuits by the most recent owner, an American hedge fund manager. In deals from 2014 to 2018, Zuckerberg bought more than 400 acres from the car dealer, Pflueger, that were originally owned by a Hawaiian king until a group of Americans conspired to sell the land to their plantation cronies. (Insider calculated the size of Zuckerberg’s properties using GIS acres to more accurately reflect their size).
And of course, there are the kuleana lands, surrounded by the former Pflueger properties, that Zuckerberg targeted in his own lawsuits.
Judging by paparazzi snapshots and Zuckerberg’s social-media posts, the oceanfront estate offers a majestic playground for the CEO of the company now called Meta. His famous sunscreen-clad hydrofoil surfing session was captured nearby in July 2020, and in June, Zuckerberg posted videos of himself shooting arrows and throwing spears on what appeared to be one of his Kauaʻi properties.
As Zuckerberg and Chan have done at other locations where they own property (including San Francisco, Palo Alto, and Lake Tahoe, California), the couple has purchased neighboring homes and lots to provide a buffer of privacy and safety. Zuckerberg’s $23 million personal–security apparatus, which includes a staff of highly trained bodyguards as well as vehicles, walls, and surveillance systems, compounds the impact on his surroundings.
“Priscilla and I visited Kauai and fell in love with the community and the cloudy green mountains,” Zuckerberg wrote in a 2016 Facebook post alongside photos of wildlife on the property. “We bought land and we’re dedicated to preserving its natural beauty,” he said, noting their desire to “plant roots and join the community.”
In March, the couple donated $4.2 million to a pandemic-related jobs program on Kauaʻi, prompting Kauaʻi County’s mayor, Derek Kawakami, in June to call Zuckerberg “a great partner.”
“There is always going to be deeply held feelings about land ownership and resource management in Hawaiʻi because of our history,” Kawakami said at the time, while also acknowledging the resources Zuckerberg had provided to assist the county’s pandemic response.
LaBolt said Zuckerberg and Chan had also contributed to the Hawaii Community Foundation, Wilcox Medical Center, and “many other local grantees.”
From the start, however, Zuckerberg’s approach to buying and securing land on Kauaʻi has engendered a degree of distrust.
Some kuleana owners alleged that Zuckerberg’s lawyers, when trying to persuade them to sell their land, hid his involvement and misled them into believing his company Northshore Kalo was a local farm growing kalo [taro] — one of the most sacred crops traditionally grown by Hawaiians. Zuckerberg’s lawyers said they weren’t misleading because those owners didn’t end up selling.
And when I spoke with Marti-Kini, she described someone who appears to have spent far more time within his walled property than planting roots in the community.
“He says he wants to be part of the community. Well, then he has to be out there. He has to touch people on a one-to-one basis, not just through his lawyers and his hired guns,” she said, referring to Zuckerberg’s extensive staff (which has had its own controversies).
Marti-Kini represents Koʻolau, where Zuckerberg lives, on the ʻAha Moku Advisory Committee, which seeks to help the state manage the land more responsibly by learning from traditional Native Hawaiian practices. Before Western contact, these practices housed and fed about 800,000 people across the islands with virtually none of the environmental problems Hawaiʻi faces today.
Despite her knowledge of the Koʻolau region, passed down from generations of her kūpuna [ancestors], Marti-Kini said Zuckerberg had rebuffed her and others’ efforts to teach him about the history of the land, including the ala loa [coastal trail] that locals say he has blocked off.
Such trails are publicly accessible by law. Marti-Kini and other locals, like Hope Kallai, a Kanaka Maoli farmer who lives near Zuckerberg and whose kūpuna have used the ala loa for generations, told Insider it runs through his property. But Zuckerberg, like past owners, has argued it meanders around his property. The state’s Department of Land and Natural Resources told Insider it hadn’t determined the trail’s location.
“We would help him steward the land. He doesn’t have to go hire people from other islands to come with guns and fences,” Marti-Kini said, alluding to the increased security since Zuckerberg moved in.
“Once he’s pono [right] with the people that live here, once he shows his aloha [respect], his caring for us, his caring for the land … all this can be resolved,” she added.
“Public access to the coastline has not changed since Mark and Priscilla purchased Koʻolau Ranch,” LaBolt said, adding that the couple “have collaborated closely with local farmers and resource managers to ensure the Ranch’s activities are optimized for agricultural use and to preserve the land’s beauty and rural character.”
The Chan Zuckerberg family office said they partnered with RKL Ranch on cattle ranching, Kolo Kai Organic Farm on turmeric and ginger farming, and an unnamed expert on Native Hawaiian plant restoration.
LaBolt didn’t disclose how much land the family had set aside for ranching, farming, and conservation, though many sections were required to be used for agricultural and conservation purposes before Zuckerberg purchased them.
Growing up, Antone “Tony” Rapozo III would often go fishing at Pīlaʻa Beach, walking through the lush valleys that lead to the secluded stretch of white sand.
Pīlaʻa Beach isn’t easy to get to for most people; it’s a steep 30-minute hike from the nearest public road. But thanks to the kuleana lands he co-owned, Rapozo could take a more direct route.
In 1894, Rapozo’s great-great-grandfather, Manuel Rapozo, a Portuguese immigrant turned Hawaiian Kingdom citizen, bought four kuleana parcels in Pīlaʻa. Manuel’s heirs have owned the properties since.
While Tony Rapozo isn’t Native Hawaiian himself, his wife, his son, and many of the Rapozo descendants and kuleana co-owners are, and several told Insider that the family had long taken pride in preserving the land in accordance with Hawaiian values of malama ʻāina and shared ownership and use.
On December 30, 2016, one of Zuckerberg’s shell companies, Northshore Kalo, which had quietly acquired shares in the properties, sued more than 500 co-owners, including Rapozo and other descendants of Manuel, hoping to force them to sell their shares.
Within three years, the family’s connection to their kuleana lands and the beach access they had used for decades had been all but severed, save for just one descendant: Carlos Andrade.
To understand the Rapozos’ story, and the broader backlash on the islands to Zuckerberg’s lawsuits, it’s important to understand how Hawaiian-owned land became so scarce.
Before Westerners arrived, Hawaiians treated land as a shared resource that no one owned or could be excluded from. But the traditional ahupuaʻa system became increasingly difficult to maintain as diseases brought by Westerners killed an estimated 80% of all Hawaiians in just 70 years, the Hawaiian studies professor Donovan Preza told Insider.
The Hawaiian Kingdom also faced threats from foreign businessmen eager to buy land and governments eager to colonize the islands, the Hawaiian historian Lilikalā Kameʻeleihiwa wrote.
To confront these threats, King Kamehameha III in 1848 began the Great Māhele [division]. This seven-year process transformed the Kingdom’s land system into one based on private property; allocated the rights to Hawaiʻi’s 4.1 million acres among the Mōʻī [monarch], high chiefs, and government; and allowed foreigners to own land.
Hoping to ultimately set aside one-third of the islands for makaʻāinana [ordinary citizens], Kamehameha also issued the Kuleana Act, which let all Hawaiians claim small lots they had lived and worked on.
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Konohiki land
Private property given to 252 konohiki [ahupuaʻa headmen] and other high-ranking Aliʻi [chiefs].
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Government land
Public land owned and managed by the Hawaiian government.
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Crown land
Private property owned by the reigning monarch but used for the benefit of all Kānaka Maoli.
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Kuleana land
Private property owned by makaʻāinana — but various obstacles meant less than 30% of those eligible got land this way.
While foreigners’ familiarity with land systems based on private property helped them acquire huge swaths of cheap land for ranches and sugar and pineapple plantations, Hawaiians faced numerous cultural, legal, and financial barriers that resulted in their obtaining — and keeping — very little by comparison, Kameʻeleihiwa wrote.
From 1846 to 1893, 75% of all government land sold — more than 485,000 acres — went to non-Hawaiians, according to Preza. And by 1890, plantation owners had leased an additional 750,000 acres of government and Crown Land — 18% of the islands.
But the largest foreign land grab happened after a group of American businessmen, conspiring with a rogue US diplomat, enlisted the US military — without authorization — to overthrow Queen Liliʻuokalani in 1893.
These businessmen, led by the pineapple baron Sanford Dole, called themselves the “Republic of Hawaiʻi,” seized about 828,000 acres of publicly owned government land — and 915,000 acres of privately owned Crown Land — and ruled Hawaiʻi for five years before ceding control, and the land they had taken, to the US.
After the US annexed Hawaiʻi in 1898, American lawmakers mostly leased that land to American landowners and the US military, despite a legal obligation to use them for the benefit of Native Hawaiians, the historian Jon Van Dyke wrote.
The one notable exception came in 1921, when the US government promised to lease 200,000 acres to Kānaka Maoli as reparations. But plantation lobbyists kept prime agricultural land out of the program, according to Van Dyke. Hawaiians were ultimately promised land that, as one American lawmaker said at the time, “a goat couldn’t live on.”
A recent ProPublica investigation revealed how, a century later, the US government had still largely failed to deliver on that promise, leaving 28,000 Kānaka Maoli on a decades-long waiting list.
Waioli — spelled Waiʻoli in Hawaiian — is a nonprofit created, managed, and endowed with its land by the Wilcox family, one of the most powerful plantation families in Kauaʻi’s history (several non-family members also sit on Waioli’s board).
The properties Zuckerberg bought from Waioli have been owned or overseen by the Wilcox family for 170 years, ever since the American missionary Abner Wilcox bought 560 acres during the Māhele land redistribution for $501 (about $17,800 today) and 50% below market rate.
Abner’s Lepeuli purchase shows how politically connected non-Hawaiians were often able to buy larger lots, at lower prices, than Hawaiians after the Māhele, the historian Kameʻeleihiwa wrote.
Abner’s sons, George Norton Wilcox and Albert Spencer Wilcox, plantation owners and politicians in the Kingdom, were members of the secret society that overthrew Queen Liliʻuokalani. George coauthored the “Bayonet Constitution,” which paved the way for the coup. Shortly after, Albert bought 984 acres on Kauaʻi that had been seized from Liliʻuokalani — without paying her a dime — according to the historian Preza.
Plantation owners also implemented a migrant-labor system that one US diplomat called the “the slave trade under another name,” according to the historian Van Dyke. The Wilcoxes paid their Chinese and Japanese workers the equivalent of $1.81 an hour today, relied on child labor, and argued that “servile labor” was necessary to make plantations successful.
In 2000, the AOL founder Steve Case bought Grove Farm, the company started by George Wilcox, for $26 million, making him Kauaʻi’s second-largest private landowner.
The 592 acres Zuckerberg bought in March from Waioli once included a Hawaiian school and kuleana parcels. Both have been gone for decades, replaced by cattle-grazing land that now doubles as Zuckerberg’s privacy buffer.
LaBolt declined to comment on whether Zuckerberg was aware of the Wilcox family’s history or Waioli’s connection to the family.
Samuel Pratt, a Wilcox heir who is president of Waioli Corporation, told Insider in a statement that “Albert and George represented Kauaʻi’s community for many years as political officials before and after the overthrow of the Hawaiian Kingdom.”
But when I asked Marti-Kini for her reaction to Zuckerberg’s latest purchase, given the Wilcox family’s history, she said she was “disgusted,” adding that the deal had “shades of modern colonialism” and “greed.”
A month after suing Rapozo and his co-owners, Zuckerberg caved to public pressure.
The lawsuit, which threatened to force a bidding war between the world’s fourth-wealthiest person at the time and hundreds of co-owners — many of them Native Hawaiian — had ignited fierce backlash, with locals marching outside Zuckerberg’s property.
At first, Zuckerberg responded by decrying “misleading stories” and framing the lawsuit as a necessary legal process to ensure he could identify and pay people who didn’t know they were co-owners. “For most of these folks, they will now receive money for something they never even knew they had. No one will be forced off the land,” Zuckerberg wrote on his Facebook page.
Some co-owners, however, including several who had long known about their inheritance, wanted the land, not the money — which in many cases would have been just a few hundred dollars per owner. Under the new partition law those owners could have refused to sell, but because Zuckerberg sued days before the new law took effect, the impasse meant the court could force them to sell at auction.
Eight days after defending himself on Facebook, Zuckerberg said he had “made a mistake” and announced in an op-ed article in Kauaʻi’s local paper that he was dropping his quiet-title actions and wanted to “work together with the community on a new approach.”
But his coplaintiff, Carlos Andrade, continued the lawsuit.
Andrade — a Kanaka Maoli retired Hawaiian studies professor who is also a descendant of Manuel Rapozo — had lived on the kuleana parcels since the 1970s. Andrade defended his lawsuit, saying he wasn’t aware of other Rapozo descendants who had tried to use, maintain, protect, or pay taxes on the land since he had moved there.
What happened next remains disputed.
In his op-ed article, Zuckerberg had said he supported Andrade’s lawsuit. According to Tony Rapozo, that support included secret financial backing.
In January 2017, Rapozo alleged in the lawsuit that Andrade acknowledged Zuckerberg was paying him “$5,000 or $6,000 per month to keep the gate locked and keep everyone, including the family and public, from accessing the kuleana parcels.”
Andrade, through his daughter, declined to be interviewed for this story.
Despite Rapozo and other co-owners’ suspicions of collusion between Zuckerberg and Andrade, the judge denied their request to investigate further and instead ordered an auction.
Andrade bought three of the four parcels, while a group of Rapozo family members bid $700,000 for the fourth. But at a “confirmation hearing,” where bidding can be reopened with a large-enough offer, Andrade outbid them, buying the fourth parcel for about $1 million.
Several co-owners have since filed a lawsuit accusing Zuckerberg of unfairly skewing the auctions by financing Andrade and misleading the court about their relationship.
LaBolt declined to comment on the allegations that Zuckerberg had paid Andrade or financially supported his legal actions but said “Dr. Andrade owns these parcels, not Mark and Priscilla.”
Before filing the lawsuits, Andrade had sent a letter to the other Rapozo descendants saying he could no longer “single-handedly bear the burden of the upkeep and financial responsibilities” surrounding the family’s kuleana parcels. But rather than asking his ʻohana [family] for help taking care of the land, Andrade urged them to sell to Zuckerberg.
In July, Rego and his wife, Primrose, invited me to visit Kepuhi Point, a lava rock cliff jutting out over the ocean below Zuckerberg’s Waipakē property, to learn more about the land’s history.
They told stories about the wave-carved pool enjoyed by generations of their kūpuna, the white flowers of the native naupaka kahakai [beach naupaka], and the endangered mōlī [Laysan Albatross] gliding overhead — Rego with a booming voice and gregarious energy, “Aunty Prim” with a gentle graciousness.
When visiting his kūpuna, Rego drives his truck to a security checkpoint on the inland side of Zuckerberg’s property, then to the ridge where they’re buried — the route sometimes changing because of the constant construction. On his most recent outing, Rego threw a friendly shaka at the guard and cruised on alone; though Zuckerberg’s guards have occasionally tailed him, Rego said.
Before these visits, Rego must give Zuckerberg’s staff 24-hour notice.
“It does feel funny as a Hawaiian who used to own this land — my family has been here for generations — I have to ask to go down,” Rego said. “It’s not just me,” he continued, adding: “Hawaiians from Big Island to Kauaʻi have seen our lands just disappear.”
The Chan Zuckerberg family office said it had granted Rego access to the sites when asked per a legal arrangement with the state.
In Waipakē, Zuckerberg has also benefited from quiet title and partition lawsuits that predated him.
In 2014, Zuckerberg bought his Waipakē property from the tech hedge fund manager Larry Bowman for a reported $66 million. Twelve years earlier, Bowman had sued Rego and other co-owners for their kuleana parcels — as Zuckerberg had sued the Rapozos — but the family members sold because they couldn’t afford to fight Bowman in court, Rego said.
Bowman didn’t respond to multiple attempts by Insider to reach him for comment.
Rego’s family lost most of their Waipakē land in 1906 when the territorial Supreme Court ignored evidence that his great-great-great-aunt, Ana Kini, had the deeds fraudulently taken from her amid threats from her second husband.
Chief Justice Walter Frear dismissed the husband’s threats toward Ana Kini as typical among “the class to which these people belonged” — she was previously married to a chief — which Rego called an example of the racism Hawaiians have long faced in American courts.
Kīlauea Plantation eventually acquired the land, Rego said. Frear was later accused of using the courts to steer land to plantations.
Despite this history, Rego and Primrose, who work as entertainers performing Hawaiian songs and dances, are among the few fortunate Kānaka Maoli who have managed to hold onto even a fraction of the land their ancestors owned before the Hawaiian Kingdom’s overthrow. The couple lives in a humble 650-square-foot house across the street from Zuckerberg’s compound, nestled between several multimillion-dollar mansions. On their 6-acre lot, they practice subsistence farming, cultivating loʻi kalo [taro patches] and other traditional Hawaiian crops.
Rego still believes that his family’s land in Waipakē was wrongly taken and should be returned. But when I asked him how he’d use it if given the chance, he offered a wildly different vision from what Zuckerberg has planned.
“It should be used for the people. I can’t live on all this land,” Rego said. “You’d have to take care of the place too, malama ʻāina,” he continued, “but something can be done where Hawaiians could be camping down there rather than being kicked out.”
Rego was referring to Kauaʻi’s growing number of unhoused individuals, who are disproportionately Native Hawaiian and in June were evicted from the county parks they’d been allowed to stay in during the coronavirus pandemic.
To Rego, Zuckerberg’s efforts to acquire so much Hawaiian land for himself aren’t any worse than those of the non-Hawaiians who came before him — they just drew more attention.
“When he did it, the world found out — that was one good thing,” he said. “The sad thing is that the world found out and then didn’t care again, and it’s still happening.”