Oprah Winfrey, who owns 1,000 acres of land on Maui, angered fans with her fundraiser after the wildfires. Here's a rundown of her history with Hawaii. (2024)

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Oprah Winfrey owns real estate around the world, but a large chunk of her property is on the Hawaiian island of Maui.

As Insider previously reported, Winfrey owns an estate in Montecito, California, which she bought for $52 million in 2001, as well as a duplex in Chicago, a home in Antigua, a ski chalet in Telluride, Colorado, and more.

But her biggest real-estate investments in terms of acreage have been in Hawaii. She owns around 1,000 acres across two towns in Maui, Hāna and Kula, local news outlets KITV4 and Maui Now reported.

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After the devastating wildfires in Maui this August, Winfrey and Dwayne Johnson launched the People's Fund for Maui and donated $5 million each.

On August 31, Winfrey and Dwayne "The Rock" Johnson, who is of Samoan descent and partially grew up in Hawaii, launched the People's Fund of Maui with a post on Instagram.

Its goal is to help the people of Maui rebuild after the wildfires that left at least 115 people dead and thousands of structures damaged or destroyed, Insider reported. The damage has been valued at as high as $5.5 billion by the National Centers for Environmental Information.

All money donated to their fund goes directly to the residents of Lāhainā, a town in Maui that was severely affected, they said.

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The response was mixed, with some criticizing them for seemingly asking for donations while they have a reported combined net worth of $3 billion. Others praised them for creating the fund and donating money.

Some fans took issue with Winfrey, who is worth close to $3 billion, according to Forbes, and Johnson, who was worth $270 million in February 2022, according to Forbes, asking people for financial help. As Insider reported, $10 million is less than 0.5% of their total wealth.

"I support Maui and the cause. But why are you asking us common folk who live paycheck to paycheck. We struggle to put food on table. Who helps us?" one person commented on Oprah's TikTok.

However, a Facebook post published by Insider received thousands of comments, with some fans coming to the defense of the duo.

"They donated $10 million! I don't understand why there is such negative reaction to this, but I must emphasize that being wealthy and accomplished doesn't obligate someone to distribute their wealth," one Facebook user wrote.

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Winfrey spoke about the backlash on "CBS Mornings" in September.

Winfrey said she'd experienced "an onslaught of being terrorized and vilified online" on CBS Mornings on September 12, Insider reported. She also called any criticism "attacks, lies, conspiracy theories."

Johnson and Winfrey have not responded to Insider's requests for comment.

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Celebrities, including Winfrey, have previously been called out for making big property purchases in Hawaii, as Native Hawaiians are priced out of the land and experience high rates of homelessness.

As well as Winfrey, Hawaii's billionaire landowners include Jeff Bezos, Peter Thiel, and Mark Zuckerberg, Forbes reported.

Billionaires have previously faced criticism from locals for making big land purchases in Hawaii, saying they are pushing up the cost of property and pricing out locals, Forbes reported.

According to the National Alliance to End Homelessness, Native Hawaiians and Pacific Islanders have the highest rates of homelessness, and the number of Native Hawaiians or Pacific Islanders experiencing homelessness increased by 19% between 2020 and 2022 — before the wildfires began and wiped out even more homes.

As ProPublica reported in 2020, legislation to begin giving land reparations to Native Hawaiians passed in 1995, with a directive to return land seized by the US government.

However, the US still owes Native Hawaiians 1,300 acres across the state, according to ProPublica.

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Oprah's first purchase of land in Hawaii was 100 acres in Kula, part of Maui's upcountry, in 2003.

Maui's upcountry is a region of Maui that includes the volcano, Mount Haleakalā. According to Hawaii Guide, it's set across the upper slopes of Haleakalā and away from the shore.

"'Upcountry' is as much a lifestyle as it is a place. Many people who live Upcountry consider themselves to be quite different from those fancy 'city-slickers' who live in places like Kahului, Wailuku, Kihei or West Maui," according to Maui Guidebook.

The biggest towns in upcountry are Pukalani, Makawao, Kula, and Haiku.

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She bought the land in Kula at the recommendation of her former trainer.

Winfrey chatted with her magazine O about her first Hawaiian purchase in 2006.

She bought the Kula land — which included these two buildings, pictured — at the recommendation of her property manager (and former personal trainer) Bob Greene.

Greene mentioned to her that he had found the perfect spot in upcountry, but was "worried that some developer might swoop up the land and build condos," according to Winfrey.

Instead, she purchased the land and "has no plan to build any condos," according to the magazine.

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She was originally going to build the "ultimate Hawaii homestead" on the land, her decorator said, but instead, she fell in love with the original house and renovated it to her liking.

"The original plan was to do a quick job on the house then think about building the ultimate Hawaii homestead," Winfrey's decorator Ellie Cullman told O in 2006.

Instead, it became a much larger renovation of the existing house. Architectural designer Jeff Wooley, of John B. Murray Architect, changed the floor plan, stripped down the house, moved the staircase, and added a huge veranda so every part of the house would have a view, O reported.

"She liked [the home's] small scale," Cullman said. "She already has a large home in Santa Barbara — this seems to go back to something real and personal."

"I love, love, love my house," she is quoted saying in the article, calling it "a real, normal" home that "feels like a nice blanket."

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The land also came with a 12-room bed-and-breakfast on 17 acres.

In 2010, Hawaii News Now reported that Winfrey was planning on turning the 12-bedroom inn into "a high-end bed-and-breakfast" for her friends and other wealthy customers.

The next year, Real Estate Maui Hawaii reported that Maui's County Council had approved her request for a "a 10-year extension on her permit to operate the vacation rental."

However, it's unclear if she ever opened the business. Winfrey did not respond to Insider's request for comment.

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In late 2021, Winfrey purchased a 3-acre property in Kula for $7 million. As she already owned the adjacent land, she was able to connect her properties after this purchase.

Maui Now reported that Winfrey purchased a 3-acre property that was adjacent to her other properties in Kula, adding to her almost 100 acres at the time.

The property, which is zoned for agriculture, also came with a 1,139-square-foot building, according to Maui Now.

Also according to Maui Now, Winfrey's properties were all owned through her companies, OW Ranch LLC, Oprah's Farm LLC, and Yellow Brick Road LLC.

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Over the past year, she has reportedly purchased four parcels of land, totaling 870 acres, for $6.6 million.

In March 2023, Maui Now reported that Winfrey spent $6.6 million on 870 acres of land in Kula.

First, two parcels of 10 acres each were sold in December 2022 to Winfrey's Los Angeles-based company Harpo Inc. for $100,000 each.

Two more parcels were sold in February 2023 by ʻUlupalakua Ranch to Harpo Inc: 520 acres for $3.89 million and 330 acres for $2.47 million.

For now, it seems that Winfrey intends to keep this land undeveloped. She did not respond to Insider's request for comment.

In addition to her upcountry land, Winfrey also owns land in Hāna, a town on the easternmost tip of Maui.

According to Maui Now, Winfrey bought "more than 200 acres of coastal land in Hāna" through 2005. It is unclear what the land is used for, and she did not respond to Insider's request for comment about its status.

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Although Winfrey has faced some criticism for buying the land, others have a different opinion since she's left much of it undeveloped and hires locals to help with upkeep.

Maui council member Yuki Lei Sugimura told local outlet KITV4 in March 2023 that she appreciated what Winfrey was doing with the land, calling agricultural land "treasured," and also praised Winfrey for hiring local residents.

"She's always been a great steward of our land, to preserve it," said Maui senator Lynn DeCoite, adding that she "wish[ed] we had more people like her," according to KITV4. DeCoite also noted that "much of the land" Winfrey has purchased has remained undeveloped.

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The 2023 wildfires aren't the first time Winfrey's land was hit by a natural disaster. During a 2019 brush fire, Winfrey opened her private road to assist with evacuations.

Maui experienced "a very active fire season" in 2019, Fire Services Chief Rylan Yatsushiro told The Maui News in December that year. Throughout the year, 25,000 acres burned, according to The Maui News, compared to the 3,900 burned acres in 2018.

Winfrey shared on X that she had opened her private road to help citizens evacuate on July 12, 2019.

"Access to the road was given to county officials immediately. This was many hours ago. Hoping for the safety of all," she wrote.

The official account of the governor of Hawaii reposted her message on X, writing, "A big mahalo to @Oprah for giving @mauicounty access to your private road for use to assist in the #Mauifire."

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As Maui rebuilds, Winfrey has been extending aid in various ways, through monetary donations, starting the fund, and distributing supplies throughout the island.

Besides starting the fund, Winfrey also visited shelters on Maui to help distribute aid in August, The New York Times reported.

She wrote about the experience on her website, Oprah Daily.

"At each hub, I asked people to tell me what they needed," Winfrey wrote. "I'm just trying to stay open and flexible."

"I'm just trying to provide and be open wherever possible. Each day presents itself with a new set of challenges and obstacles to try to overcome," she added.