From pineapples to billionaires: Discovering modern-day Lanai

“Wow, I’m jealous,” says my buddy, Justin. “I’ve never met anyone who’s been to Lanai.”

Considering he’s about to spend three weeks in Antarctica, I’m not sure who has more traveler’s envy. But my sojourn to Hawaii’s so-called “Pineapple Island” is undeniably a punch off my bucket list.

My wife and I have made dozens of trips to the state’s Big Four — Oahu, Hawaii, Maui and Kauai — plus a foray to oft-overlooked Molokai that failed spectacularly thanks to a mouse invasion. Lanai’s the last in my collect-‘em-all catalog – the smallest and least-populous of the islands folks can visit, since Kahoolawe’s an uninhabited former bombing range and tiny Niihau’s off-limits beyond the family that owns it.

Oh yes, Lanai’s in private hands, too. A decade ago, Oracle founder and chairman Larry Ellison – the planet’s seventh-richest human – bought 98 percent of it from a corporate offshoot of pineapple giant Dole.

Ellison paid 300 times the cool $1 million fruit tycoon James Dole dropped in the Roaring ’20s for the 140-square-mile rock. Dole created an enormous plantation complete with quaint company town. But by the early 1990s, production had shut down in favor of luxury golf resorts.

Three years before Ellison bought the island, the National Trust for Historic Preservation called tiny Lanai City one of America’s “most endangered historic places.”

Ellison has long been one of Silicon Valley’s most colorful, combative and controversial CEOs; one has to think he got a kick from buying the island his longtime nemesis, Bill Gates, once rented out to get married.

But locals we meet have nothing but praise.

When COVID shuttered the tourist trade that’s the island’s life blood, Ellison stopped charging merchants rent for nine months, says Kathy Carroll, whose family art gallery fronts downtown’s Dole Park. “People wouldn’t have made it otherwise,” she says.

Now Ellison, who grew up poor on Chicago’s South Side, is building badly needed affordable housing. “Well, it’s Larry’s take on affordable housing,” laughs Carroll. “Every unit has flat-screen TVs and a solar roof from Tesla.” (Ellison sits on the board of that company, which is run by fellow centibillionaire Elon Musk.)

Ellison also won plaudits for resurrecting his new hometown’s movie house. Dole commissioned the Lanai Theater in 1926, but like the pineapple industry, it went bust in the 1990s. Two years – and a $4 million renovation – after Ellison’s arrival, the bijou was reborn as the Hale Keaka (“picture house”). Offerings while we were in town included “Black Adam” (starring Polynesian superstar Dwayne Johnson) and a George Clooney-Julia Roberts romcom called, aptly enough, “Ticket to Paradise.”

Though a framed black-and-white in the lobby reveals a grubby marquee where tickets cost a buck (50 cents for kids), the cinema now resembles a Zen retreat center with smooth-planed cypress ceilings. That’s in keeping with Ellison’s well-known penchant for Japanese art and architecture.

So is his retconning of the venerable Lodge at Koele, which thanks to Ellison is now the Four Seasons Sensei. Carroll says Ellison kept paying the entire staff throughout the pandemic – enlightened self-interest, perhaps, but still far from Ellison’s less-than-charitable reputation.

Ellison owns all three hotels on the island – the Sensei, another Four Seasons overlooking the ocean 20 minutes away, and the boutique Hotel Lanai, which began life as a plantation overseer’s spread.

Thanks to Airbnb, we find a much more affordable but delightfully appointed bungalow owned by a Maui-based artist. To paraphrase Spinal Tap’s Nigel Tufnel, “We’re not Four Seasons material.”

Still, since we’ve come to the island for our 25th wedding anniversary, I try to make dinner reservations at the ultra-swanky Sensei by Nobu – only to learn it’s exclusively for hotel guests only. Thankfully, a friend who once worked closely with Ellison pulls some strings to get us in for the big night. Call it Silicon Valley networking, island-style.

Not everything Ellison has touched on Lanai has turned to gold. In 2013, the mogul bought commuter carrier Island Air to shuttle guests to his island; three years later, he sold it amid a flood of red ink, and the buyer subsequently folded. (We flew in and out on the same tiny Mokulele Airlines prop planes we took to Molokai 10 years back. They evoke Volkswagen microbuses with ironing boards welded to the roof. Visitors also have a ferry option.)

Now Ellison is paying $5 million to lengthen the runway at minuscule Lanai Airport to accommodate more private jets. Some elected leaders grumble about widening the gap between the haves, the have-nots and the have-everythings.

Meanwhile, the state of Hawaii – which owns the 2 percent of Lanai that Ellison doesn’t – is proposing to develop an agricultural park for small farmers. One county councilman calls it “a chunk of land of our own that Larry Ellison won’t have a say in.”

But while development tussles have riven Molokai over the years, Lanai City seems to breathe the Hawaiian value of ohana (family). The rows of tin-roofed plantation cottages – some charmingly restored, others scruffily casual – evoke the architectural quaintness of Lahaina, Maui’s old whaling town, without the touristy.