13 Billionaires Who Did More for Hawaii Than You Think – #13 Confused Locals for Years and Still Does

One billionaire handed Hawaii $150 million in a single day.

Another owns 98 percent of an entire island and gave us almost nothing.

After 30-plus years on Oahu, and more neighbor island trips than I can count, I’ve watched both kinds up close. I’m not a tour guide. I’m a local who pays attention.

Here are the 13 stories worth knowing. Number 13 is the strangest act of generosity I’ve ever seen.

Marc Benioff Wrote the Biggest Check in Hawaii’s History

Start with the biggest single day. By his family’s own tally, the Salesforce founder has put more than $250 million into Hawaii.

In March 2024, he and his wife Lynne gave $150 million in one day.

That’s $100 million to remake Straub in Honolulu, now Straub Benioff Medical Center, and $50 million to Hilo Medical Center, which woke up as Hilo Benioff, for a birthing center, an ICU, and neurosurgery. He’s also given away more than 440 acres in Waimea, 282 of them set aside for affordable housing. Plus fire trucks. Plus medical helicopters.

Now the messy part. I have a friend in Waimea, up where the fog rolls in smelling like eucalyptus and wet grass. For years, she’d talk about a mystery buyer grabbing land through anonymous LLCs. Nobody knew who.

Then NPR named him in February 2024. More than 600 acres, at least six different LLCs, all tracing back to the same California P.O. box.

The $150 million landed six days after that story broke.

He told NPR, “I came to Hawaii for the first time and fell in love.” I believe him. I also know how to count to six. Hold that tension, because the next guy on this list has none of it.

Jay Shidler Handed UH a Money Machine Nobody Talks About

Here’s the name most readers won’t know, which is exactly the point.

Jay Shidler is a Honolulu real estate investor who has committed $238 million to the UH business school that now carries his name. It’s the largest gift in the university’s history.

The structure is the genius part. Most of it isn’t cash. It’s 99-year ground leases under office buildings in nine mainland cities.

The contracts add up to $2.1 billion in lease income, about $21 million a year averaged over their life, and when the leases run out, UH keeps the land too.

The university’s own math puts the full package north of $7 billion.

Do that math for a second. The $238 million headline is the small number. He handed the school a mango tree instead of a bag of mangoes… the fruit never stops.

He’s not even Hawaii-born. He arrived in 1964, graduated from Manoa in 1968, and has spent the decades since paying it back. Zero drama, zero press tours. The next billionaire is his opposite. He’s everywhere in Hawaii, and most locals still can’t spell his name.

Pierre Omidyar Has Been Quietly Paying Hawaii’s Bills for 20 Years

The eBay founder actually lives in Honolulu, and his fingerprints are all over this state. The quick scorecard:

• $100 million plus into Hawaii causes since 2006
• A $50 million fund at the Hawaii Community Foundation
• The Ulupono Initiative has pushed over $79 million into local food, clean energy, and water
• Honolulu Civil Beat, the investigative newsroom he founded in 2010
• $500,000 to Maui Strong within hours of the Lahaina fire

He almost never gives interviews, but he once put it simply: “Because we live here, because we want to raise our family here… we want to invest to make this a better place.”

My controversial take, and I’ll own it. The best thing he funds is Civil Beat, and Civil Beat’s job includes investigating billionaires like him. They literally published a hard piece on their own owner. That’s rare, and I respect it.

His record isn’t clean though. His Hanalei resort plans drew a petition with more than 3,400 signatures, and his big Kauai dairy dream collapsed after five years of fighting. Even careful money makes waves here. The next fortune on this list made waves for 35 years after its owner died.

Harry Weinberg Died 35 Years Ago and Still Feeds Hawaii Families

Try this test next time you’re running errands on Oahu. Count the buildings with “Weinberg” carved over the door. The Hawaii Nature Center in Makiki. The EMS building at the Waianae health center. The Kukui Center downtown.

There are 183 of them across the islands.

There’s a reason. Harry Weinberg was a Baltimore kid who quit school at 12, got rich on real estate and bus companies, took control of Honolulu’s buses in the late 1950s, and became the largest individual real estate investor in Hawaii.

He left $900 million to his foundation in 1990.

Today it holds about $3.1 billion and pumps roughly $12 million a year into Hawaii nonprofits. His rule was blunt. Any building taking more than $250,000 of his money wears his name forever. Vain? A little.

But his foundation still owns about 200 commercial properties across the islands, worth more than a billion dollars, and at his death nobody privately held more Hawaii real estate.

The 2026 inventory of everything billionaires now own across Hawaii makes Harry’s empire look like a beach concession stand, and seeing it mapped out changed how I drive around my own island.

A dead man’s money, still feeding families every month, 35 years later. Only one gift in Hawaii history has outlasted it.

Charles Reed Bishop Kept a Promise That Grew Into $15 Billion

Here’s the unexpected one. The most important “billionaire” in Hawaii’s history never saw a billion dollars in his life. Charles Reed Bishop was a New York banker who arrived in 1846, married Princess Bernice Pauahi, and founded the bank that became First Hawaiian.

When Pauahi died in 1884, she willed about 375,000 acres, nearly 9 percent of all Hawaiian land, to create Kamehameha Schools.

This is the part that gives me the “chicken skin”. The estate was land-rich and cash-poor. So Bishop paid for the first school buildings out of his own pocket. He built the Bishop Museum in 1889 to honor her.

Today, that endowment is worth $15.2 billion.

It educates nearly 7,000 keiki from preschool through high school, 5,400 of them on three campuses, runs 30 preschools, and reaches 40,000 more Hawaiian learners a year.

One marriage. One will. One grieving husband who kept his promise for the rest of his life. Show me the tech founder whose gift will still be working in 140 years. There’s one more old-money ghost on this list, and she left behind an actual palace you can walk into.

The $45 Tour Inside a Billionaire Palace Most Locals Never See

In 1935, the “richest girl in the world” honeymooned through the Islamic world, fell hard for Hawaii on the last stop, and built Shangri-La on the rocks past Diamond Head.

Doris Duke filled it with about 4,500 pieces of Islamic art, one of the most important collections in America, and her foundation runs it as a museum today.

I took my daughter a few years back. You smell the salt spray hitting the seawall before you see the tilework, and the pool sits so close to the ocean that you hear waves slap while you stand in a Persian courtyard.

Only about 14,000 visitors a year get in, because a county permit caps the tours and the estate hides inside a residential neighborhood. Here’s how the smart ones do it.

General admission runs $45, but kamaaina pay $20 on the Thursday and Friday tours booked through the Honolulu Museum of Art, or $25 on the newer Saturday shuttle from Bishop Museum, and every ticket includes same-day admission to the host museum. Two museums, one booking.

💡 Insider tip. Tickets drop at 10 a.m. Hawaii time on the first Thursday of every month and vanish fast, so set a reminder.

Planning ahead is the entire game in Hawaii, honestly. Most of the 15 moves that save visitors real money and headaches here happen before anyone leaves home, and this ticket trick is exactly that species of move. Now, from the quietest palace in Honolulu to the loudest backlash Hawaii ever cooked up.

Oprah and The Rock Gave Six Times What the Internet Roasted Them For

You remember the roasting. In August 2023, Lahaina is still smoking, and Oprah and Dwayne Johnson launch the People’s Fund of Maui with $10 million while asking the public to chip in.

The internet went nuclear. Two stars worth billions, passing the hat? Oprah said she was “terrorized and vilified” online. The Rock later admitted, “I could have been better.”

Here’s what the anger machine never circled back to. That fund paid $1,200 a month for six months, direct deposit, to about 8,100 adults who lost their homes.

Nearly $60 million went out the door in six months.

The bulk of it came from the two of them personally. Read that sentence again, because nobody ever did. I volunteered sorting donations that fall, and the aunties next to me went from rolling their eyes to nodding slow.

The famous land grab math collapses too. Her 870 Kula acres at about $7,600 an acre sounds criminal until you learn it’s unbuildable ag land under a conservation easement, with no water rights. The outrage was tastier than the facts. It usually is.

And it’s still not the strangest giveaway on this list. That one’s waiting at number 13. First, the man who sued Hawaiian families and then spent eight years apologizing with his wallet.

Mark Zuckerberg Is Still Paying Off One Terrible Decision

No sugarcoating the start. In December 2016, companies tied to Zuckerberg filed quiet title lawsuits against hundreds of part-owners of kuleana parcels, Native Hawaiian family lands from the 1850s, inside his Kauai estate.

The backlash was volcanic. A month later, he dropped the suits and wrote, “We understand that for Native Hawaiians, kuleana are sacred… We want to make this right.”

The receipts since then are real. $20 million plus to Kauai nonprofits. $1 million after the 2018 floods. $4 million to rescue Alakoko Fishpond, the island’s largest. A standing $1 million a year fund that backed 25 Kauai nonprofits just last fall.

Meanwhile, his Koolau Ranch has swollen past 2,300 acres with over $300 million sunk in, including the 5,000-square-foot underground shelter Wired exposed. He shrugs it off as “a little shelter, it’s like a basement.”

A man is funding the fishpond down the road while building a doomsday basement above it. You tell me what that means. The next billionaire never needed a bunker, because he was born here.

Steve Case Is the Only One Who Actually Grew Up Here

This one’s personal for a lot of us. The AOL founder was born in Honolulu in 1958, Punahou grad, fourth-generation kamaaina, the kind of kid who grew up climbing banyan trees and bodysurfing.

When Grove Farm on Kauai was nearly broke in 2000, he bought it for $26 million, and his family has run it as a long-game land company ever since.

The good list is long. $1 million to Maui rebuilding three days after the fire. At least $10 million to Punahou. 4,000 plus workforce housing units in the pipeline. A 2025 offer to sell the state 1,000 acres of prime ag land at Kapaia for $39 million, to keep it farmed.

The complicated list is real too. Ex-shareholders sued him over the Grove Farm purchase, claiming insider dealing. He won at trial in 2008.

Earthjustice has fought Grove Farm’s stream diversions for years, and water is life here. That gap, between the paradise visitors buy and the realities locals quietly live with, runs through every name on this list.

Local boy doesn’t mean free pass. At least he answers his critics. The next guy answers nobody.

Larry Ellison Owns 98 Percent of an Island and Gave Almost Nothing

In 2012 the Oracle founder paid $300 million for 98 percent of Lanai. Both resorts. The grocery store. The gas station. The water utility. A third of the housing, and the company employing 400 people on an island of 3,000.

I went to see it myself, still skeptical. The Expeditions ferry from Maalaea runs about $30 and takes a little over an hour, salt wind in your face the whole crossing. And parts of Lanai City genuinely charmed me.

Ellison reopened the community pool the last owner had padlocked, heated, free for residents. He put $4 million into restoring the 1930s movie theater, where a ticket still costs about ten bucks. He built 76 affordable rentals.

I swam laps that morning with three aunties, and one told me flat out, “Lucky we live Hawaii, yeah? Even when one haole owns da pool.” We laughed. Complicated laughter.

Because Bloomberg found the other ledger. Housing leases that can evict you if you lose your job with his company. Business leases cut to 30 days.

In June 2022, exactly ONE house was for sale on the entire island. One.

Listed at $7.9 million where the median household earns $59,000. Everyone who falls for Hawaii hits some version of that math eventually, and the 11 warnings from people who actually moved to Hawaii all orbit it.

After the Maui fires, his neighbors across the channel? No publicly disclosed donation. Not a dollar on the record.

Is half a billion in company-town spending generosity, or just renovating your own property? The next man made the opposite mistake. A giant promise with a slow wallet.

Jeff Bezos Made a $100 Million Promise Maui Is Still Waiting On

Days after Lahaina burned, Bezos and Lauren Sanchez pledged $100 million, the single largest fire commitment by anyone. Maui threw him a parade that week, and fair enough. Help is help.

Then the follow-up reporting landed.

Five months in, only $15.5 million had moved.

A West Maui state senator told Fortune, “Nobody’s heard anything at all.” Since then it’s been a slow drip. Maui Food Bank. Boys & Girls Clubs. Land trust money in 2025. This February, $1.5 million in Lahainaluna scholarships and $2 million for wildfire research. Real gifts.

But no public accounting has ever shown the full $100 million out the door. His people say the rest “will be distributed in the coming years.”

Meanwhile only 192 homes stand rebuilt in Lahaina as of this spring, and about 849 families were still in FEMA housing.

The needs revealed themselves a long time ago, brah. The quietest man on this list watched all of it and said nothing. He always says nothing.

Michael Dell Never Says a Word About Hawaii

Dell owns more of Hawaii’s luxury skyline than almost anyone. The Four Seasons Maui at Wailea since 2004. The Four Seasons Hualalai on the Big Island since 2006, where rooms start around $1,700 a night and where he just spent $400 million more to buy the 491 acres under the resort outright.

The seller? Kamehameha Schools. Pauahi’s land, again. It never stops being the center of the story.

The man clearly believes in this place. He just won’t say so. I’ve searched for years and cannot find one public quote from him about Hawaii. Not one.

His giving here is thinner but it landed where it counted. $1 million toward the Olowalu fire station West Maui has needed for decades.

And in the weeks after the fires, his Wailea resort turned a ballroom into beds for displaced workers and first responders and ran a relief fund for its own staff. Ask anyone who slept there that August how much that mattered.

So is he a benefactor or a careful landlord? Honestly… probably a landlord.

He makes the list because that fire station money filled a hole the county left open for years, and because his silence makes everyone else’s speeches sound cheap. Which brings us, finally, to number 13. Nothing on this list prepares you for him.

The Billionaire Who Handed Beachfront Mansions to Homeless Families

Genshiro Kawamoto confused me for years. The Tokyo property tycoon owned around 30 properties along Kahala Avenue, Honolulu’s fanciest street.

In 2007 he handed eight multimillion-dollar mansions, rent-free, to low-income Native Hawaiian families. Up to ten years. Utilities only. He picked them from about 3,000 letters, favoring working single mothers, and handed each family ten hundred-dollar bills for moving money.

The first family, Dorie-Ann Kahale and her five daughters, moved in straight from a homeless shelter to a white-columned house worth nearly $5 million.

The rent hike that had put them in that shelter? $800 a month to $1,200.

I used to jog Kahala Avenue back then, plumeria sweet in the morning air, and the street looked unreal. Kids’ rubber slippers piled outside a marble entryway here. Next door, one of his empty mansions rotting.

Weeds to my waist, giant stone lions guarding broken windows, mildew rolling out the open doors. The most generous man on the block was also the worst neighbor on it.

It ended hard. Arrested in Tokyo for tax evasion in 2013, he sold everything to Alexander & Baldwin, $128 million across two deals. The families got time to relocate, then it was over.

He died in 2024 at 91, months after finishing his prison term, and today you’d never know any of it happened. Hawaii is good at erasing whole eras like that. The 20 legendary Hawaii spots locals still grieve vanished the same quiet way, several without even a goodbye.

Was Kawamoto’s experiment aloha, or an art project with human beings as the medium? I still can’t decide. Maybe that’s the honest ending.

What 37 People Owning This Much of Hawaii Really Means

So here’s the takeaway, plain. Billionaire money built our hospitals, our biggest school, our museums, and paid fire survivors’ rent. That’s real, and pretending otherwise insults the families living in homes it built. But hold this number too.

37 ultra-wealthy people now own at least 218,000 acres of Hawaii, over 10 percent of all private land, while making up 0.003 percent of the population. That’s not my math. It’s Forbes math, and Forbes thinks the real number is higher.

One guy on r/Hawaii called it “recolonization in a more friendly looking font,” and I haven’t found a clean rebuttal yet. The same squeeze is quietly ending the middle class Hawaii vacation, and those numbers are starker than anyone admits.

There’s a double bind locals talk about over coffee. Give quietly, we assume you gave nothing. Give loudly, we call it PR. Maybe the real measure is this. Does the gift hand power back, like Pauahi’s land or Shidler’s lease machine? Or does it just decorate the cage?

Next time you pass a Weinberg building or a Benioff hospital sign, ask yourself which one you’re looking at. I’m still asking. 🤙