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  • Writer's pictureAndre Watson

Yachts, parties and private islands: The indulgences of real estate’s richest

From floating mansions to private Drake performances, here's how the industry's 1 percent spend their millions


Clockwise from top left: a Bugatti Chiron; Drake; a “Madsummer” yacht; Manny Khoshbin’s 70,000-square-foot property; and the Four Seasons Hotel in Lanai

Remember the bad old days in New York? The 1970s had the city on the precipice of fiscal ruin, but a mouthy tax attorney named Steve Ross bet big on the metropolis that many landlords were ready to give up on.

Ross’ Related Companies was part of a class of modern-day real estate titans that would emerge from those ashes, but once you’ve transformed the skyline of a city often described as the capital of the world, what else is there to do? With a net worth of $4.5 billion and a place in real estate lore, Ross thought he’d buy himself a football team.

A decade after Ross spent more than $1 billion to acquire the Miami Dolphins, America has entered a new era of property titans. Real estate’s elite have always loved shiny toys and flashy parties. Now, some of the richest among them are turning the world into a playground for the ultra-wealthy.

Year of the yacht

In the rich folks’ toy box, the superyacht is nothing new. What is new is an unprecedented surge of purchases. Some 887 of them were sold last year, almost double the number sold in 2020, leaving the wealthy to contend with a shortage and seemingly endless waiting lists.

But before taking a look at the boats of the yachted gentry, let’s consider the yachtless among us — including Linda Macklowe, who lost hers in her divorce from 432 Park Avenue developer Harry Macklowe.

When the former couple couldn’t agree on the value of their art collection, accrued over the course of their marriage, a judge decided it should be auctioned off. After the second round of bidding in May, it brought in a record $922.2 million.

You can split money in half. You can’t split a boat. Long rides on the yacht, named “Unfurled,” were once a passion the Macklowes shared. “Unfurled“ now belongs to Harry.

While some go for the latest and greatest, luxury spec home developer Todd Michael Glaser’s tastes skew more vintage. Glaser and his 62-foot “Sea Tabby,” built in 1938, have been together for nearly 12 years. It still has all the original furniture, along with three state rooms and a full kitchen.

Florida kingpin Jeffrey Soffer is willing to share his superyacht, “Madsummer” — for $1.6 million a week, according to a rental listing. NFL legend Tom Brady and his supermodel wife, Gisele Bundchen, were spotted on it last year.

At that price, “Madsummer“ may be the superyacht to end all superyachts. It boasts a beach club, helipad, daycare center, spa and indoor and outdoor cinemas — a “floating mansion” in every sense of the word.

Ostentatious bashes and personal playgrounds

Brady hasn’t just taken Soffer’s yacht for a spin — he’s next-door neighbors with the developer on Indian Creek, a 300-acre Miami island where other high-profile residents have included models Adriana Lima and Soffer’s ex-wife, Elle Macpherson, as well as Ivanka Trump and Jared Kushner.

Oracle co-founder Larry Ellison is playing landlord to the people of Lanai, the Hawaiian island he bought 98 percent of in 2012 for $300 million.

Ellison moved to Lanai full-time during the pandemic, and he’s quickly turning it into a playground for other big-name billionaires such as Elon Musk and Tom Cruise, who fly or sail in, coming and going as they please.

Ellison also owns Lanai’s grocery store, gas station, newspaper and the Four Seasons resort, which employs most of the island’s population.

Expensive boats and private islands are nice, but there’s nothing like a party. Anyone in the industry can tell you that real estate wealth shines most when the elites put on a night to remember.

New York retail magnate Jeff Sutton reportedly spent $25 million on his daughter’s wedding in Puglia, Italy, including $5 million on chartered jets to transport guests. When the big day came, the billionaire father of the bride made a grand entrance in a horse-drawn carriage.

For his daughter’s bat mitzvah at the Rainbow Room in 2016, developer Ben Ashkenazy hired rapper Drake, who performed his then-hit song “Hotline Bling.”

The old guard and the new

Cars aren’t just a way to get from A to B. Glaser loves his antique cars, especially his old Ferrari and Land Rover, and he relishes early morning drives on the weekend.

Blackstone CEO Stephen Schwarzman, who said his father was always happy with just two cars, has a Porsche 911, an Audi A4, a Mini Cooper and a BMW 645 CI that goes from 0 to 60 in 5.6 seconds.

These collections are impressive to most, but they’re modest compared to that of Southern California real estate tycoon and social media sensation Manny Khoshbin.

The Khoshbin Company specializes in retail and office properties, although you wouldn’t know it from Khoshbin’s internet presence. The super car connoisseur’s YouTube channel is all automotive content, the thumbnails a gallery of his many expensive rides — so many, in fact, that last year he bought a 70,000-square-foot property to store them.

The “House of Khoshbin” is a palatious monstrosity of mirrored walls, Roman columns and gilded murals of cherubs on every floor. The garage is still unfinished, but it will house Khoshbin’s Bugattis, Porsches and the rest of his fleet.

In an industry where showy displays of wealth are the norm, fleets of sports cars or superyachts make for a great flex. But some billionaires prefer not to showboat.

West Coast developer John Sobrato, who spends up to 18 weeks out of the year on his yacht, said he sees it not as a luxury asset but as an extension of his home.

“We’ve had the same boat now for 17 years, which is unheard of in the industry,” he told the Nob Hill Gazette in a 2019 interview.

Larry Silverstein’s elusive, 175-foot “Silver Shalis” tends to generate local headlines when it makes a rare appearance. It was spotted in Maine last summer, and it popped up in Fort Lauderdale in January.

The “Silver Shalis” is an oasis of luxury, with a glass elevator, a swimming pool, a dining area and an art collection. Silverstein purchased it in 2010, reportedly for more than $30 million.

Asked by TRD about the yacht’s price in a 2011 interview, Silverstein demurred.

“That’s irrelevant,” he said.

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