Real-Estate Scions Are Breaking a Cardinal Rule: Never Sell
The office-market downturn is forcing some of the city’s multigenerational families to make emotionally fraught decisions
5 min
William Rudin, scion of one of New York City’s premier real-estate dynasties, says his grandfather built a property empire by following a cardinal rule: Never sell.
While the city’s office market wobbled during economic downturns, values and cash flows would always recover because workers came back during good times.
But last year, Rudin sold control of a 30-storey office tower in downtown Manhattan his family developed in the 1960s. This fall, the family agreed to part with 80 Pine Street, another financial district tower, after anchor tenant American International Group left.
“The world has changed,” said Rudin, the 69-year-old co-executive chairman of his family’s firm. “We have to take a cold hard look at our business in order to make sure there’s a foundation for the next generation.”
The office market’s severe downturn is forcing some of the city’s multi-generational family owners to do something they managed to avoid during world wars, financial meltdowns and a global pandemic: sell their core properties.
Families like the Rudins and the Kaufmans built their New York empires by passing these buildings from one generation to the next. The office properties steadily rose in value and provided a comfortable living for an expanding number of children, grandchildren, nieces and nephews.
“We and the other families did not sell,” said Jonathan Iger, chief executive of Sage Realty, the management firm running the 100-year-old Kaufman real-estate business founded by his great grandfather. “You see yourself through the dips and you come out—not just fine, but more than fine.”
Today, U.S. office vacancies are near record levels and demand looks permanently impaired by remote work and by companies doing more with less space. Properties that had been reliable cash cows now require substantial upgrades or other capital infusions to replace departing or shrinking tenants.
For many families in their third and fourth generation of ownership, it makes more sense to sell for whatever they can get. The Kaufman family agreed to sell a downtown office tower this year and are marketing another one in Midtown. Like others, the Kaufmans are selling the family jewels at values significantly below what they were five years ago.
Tracking the precise number of sales by these families is tricky. But real-estate investment banking firm Eastdil Secured says that New York real-estate families have sold about 10 office buildings over the past 24 months. In the previous decade there were fewer than five such deals.
“Instead of 50 different aunts and uncles getting distributions, they’re getting capital calls,” said Gary Phillips , an Eastdil managing director.
Individuals and small private owners have stakes in about one third of the 350,000 office properties tracked by data firm CoStar Group. The decision by a number of families to sell is part of a natural evolution under way in New York and other big cities.
Often the buyers are large developers or investment firms with the deep pockets to convert these buildings into other types of properties more in demand, especially rental apartments.
“Many landlords are going through this process,” said Michael Cohen, the patriarch of one of three New York families that led a sale of a Madison Avenue office building this year. The new owner plans to demolish it and convert the property to a different use.
These can be emotionally fraught decisions. Over the decades, more family members have gained a stake in the properties. They often have widely varying financial needs or incentives.
Tensions between family members who want to hold and those who want to sell have always simmered in the background. Today’s tough times have intensified these battles.
When values and profits are rising, “it’s harder to make a case to sell. Now there’s a sense of: ‘Wait a second. We’re not seeing improvement,’” said Peter Boumgarden, director of the Koch Center for Family Enterprise at Washington University in St. Louis.
New York City dynasties have played a major role in real-estate growth since the late 1800s. Many of the early family members were European immigrants who started real-estate companies that their children and grandchildren grew into empires. The Dursts, Milsteins and Trumps are among the New York families to shape the cityscape.
Families were able to hold on to their buildings by following low-debt strategies, which insulated them from market downturns and positioned them to profit when markets recovered.
Lately, some office markets are showing a few positive signs, as bosses call workers back to the office. But the buildings that stand to benefit are new ones or those in top-tier locations, like Rockefeller Center, that have gone through extensive upgrades. Tenants are moving to those amenity-laden spaces to give their employees more of an incentive to put up with lengthy commutes.
Many of New York’s real-estate families own older buildings in less desirable locations, offering few of the special features that attract tenants. They also have large vacancies that are costly to fill these days. Landlords feel the need to offer free rent and spend heavily on new interiors to compete.
“There’s little incentive for landlords to make a significant contribution,” said Stephen Siegel, chairman of global brokerage for real-estate services firm CBRE Group . “It’s money in and really no money out.”
Even with recent sales, the Rudins are keeping most of their office portfolio, which includes 14 other New York buildings. So are the Kaufmans. Some families are even making big investments in their aging office buildings, betting that they will be among the winners.
The Gural family last year led a group that agreed to invest new equity into the DuMont Building, on Madison Avenue, which the family has controlled for over 60 years. Partners who were used to getting disbursements from the property had to reach into their pockets to pay their share for capital improvements and paying down debt.
“It’s called a capital call, which is the most dreaded term in our industry,” said Jeffrey Gural , chairman of GFP Real Estate, which manages the family’s properties.
But the decision paid off. By putting in fresh money, the partners were able to negotiate a loan extension with the building’s creditors and attract tenants.
“I have yet to sell a building where I didn’t regret selling,” Gural said.
Yet other families are choosing to walk away from properties—even if they reinvested in them. The Rudins recently spent $100 million on renovations at 80 Pine’s lobby and building systems, adding a terrace and dining room. Now, William Rudin considers forking over any additional money a waste.
“Even if we spent money to fix up the building, the ceilings are too low, there are a lot of columns, the floors are too big,” he said. “It became clear to us we needed to stop putting capital back into the building.”
It was a gut-wrenching decision, letting go of what amounted to a family heirloom.
“When I go by 80 Pine Street, I remember the good times and I remember the bad times,” Rudin said. “But you’ve got to move on.”
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Weary of ‘smart’ everything, Americans are craving stylish ‘analog rooms’ free of digital distractions—and designers are making them a growing trend.
5 min
James and Ellen Patterson are hardly Luddites. But the couple, who both work in tech, made an unexpectedly old-timey decision during the renovation of their 1928 Washington, D.C., home last year.
The Pattersons had planned to use a spacious unfinished basement room to store James’s music equipment, but noticed that their children, all under age 21, kept disappearing down there to entertain themselves for hours without the aid of tablets or TVs.
Inspired, the duo brought a new directive to their design team.
The subterranean space would become an “analog room”: a studiously screen-free zone where the family could play board games together, practice instruments, listen to records or just lounge about lazily, undistracted by devices.
For decades, we’ve celebrated the rise of the “smart home”—knobless, switchless, effortless and entirely orchestrated via apps.
But evidence suggests that screen-free “dumb” spaces might be poised for a comeback.
Many smart-home features are losing their luster as they raise concerns about surveillance and, frankly, just don’t function.
New York designer Christine Gachot said she’d never have to work again “if I had a dollar for every time I had a client tell me ‘my smart music system keeps dropping off’ or ‘I can’t log in.’ ”
Google searches for “how to reduce screen time” reached an all-time high in 2025. In the past four years on TikTok, videos tagged #AnalogLife—cataloging users’ embrace of old technology, physical media and low-tech lifestyles—received over 76 million views.
And last month, Architectural Digest reported on nostalgia for old-school tech : “landline in hand, cord twirled around finger.”
Catherine Price, author of “ How to Break Up With Your Phone,” calls the trend heartening.
“People are waking up to the idea that screens are getting in the way of real life interactions and taking steps through design choices to create an alternative, places where people can be fully present,” said Price, whose new book “ The Amazing Generation ,” co-written with Jonathan Haidt, counsels tweens and kids on fun ways to escape screens.
From both a user and design perspective, the Pattersons consider their analog room a success.
Freed from the need to accommodate an oversize television or stuff walls with miles of wiring, their design team—BarnesVanze Architects and designer Colman Riddell—could get more creative, dividing the space into discrete music and game zones.
Ellen’s octogenarian parents, who live nearby, often swing by for a round or two of the Stock Market Game, an eBay-sourced relic from Ellen’s childhood that requires calculations with pen and paper.
In the music area, James’s collection of retro Fender and Gibson guitars adorn walls slicked with Farrow & Ball’s Card Room Green , while the ceiling is papered with a pattern that mimics the organic texture of vintage Fender tweed.
A trio of collectible amps cluster behind a standing mic—forming a de facto stage where family and friends perform on karaoke nights. Built-in cabinets display a Rega turntable and the couple’s vinyl record collection.
“Playing a game with family or doing your own little impromptu karaoke is just so much more joyful than getting on your phone and scrolling for 45 minutes,” said James.
Screen-Free ‘Escapes’
“Dumb” design will likely continue to gather steam, said Hans Lorei, a designer in Nashville, Tenn., as people increasingly treat their homes “less as spaces to optimise and more as spaces to retreat.”
Case in point: The top-floor nook that designer Jeanne Hayes of Camden Grace Interiors carved out in her Connecticut home as an “offline-office” space.
Her desk? A periwinkle beanbag chair paired with an ottoman by Jaxx. “I hunker down here when I need to escape distractions from the outside world,” she explained.
“Sometimes I’m scheming designs for a project while listening to vinyl, other times I’m reading the newspaper in solitude. When I’m in here without screens, I feel more peaceful and more productive at the same time—two things that rarely go hand in hand.”
A subtle archway marks the transition into designer Zoë Feldman’s Washington, D.C., rosy sunroom—a serene space she conceived as a respite from the digital demands of everyday life.
Used for reading and quiet conversation, it “reinforces how restorative it can be to be physically present in a room without constant input,” the designer said.
Laura Lubin, owner of Nashville-based Ellerslie Interiors, transformed a tiny guest bedroom in her family’s cottage into her own “wellness room,” where she retreats for sound baths, massages and reflection.
“Without screens, the room immediately shifts your nervous system. You’re not multitasking or consuming, you’re just present,” said Lubin.
As a designer, she’s fielding requests from clients for similar spaces that support mental health and rest, she said.
“People are overstimulated and overscheduled,” she explained. “Homes are no longer just places to live—they’re expected to actively support well-being.”
Designer Molly Torres Portnof of New York’s DATE Interiors adopted the same brief when she designed a music room for her husband, owner of the labels Greenway Records and Levitation, in their Lido Beach, N.Y. home. He goes there nightly to listen to records or play his guitar.
The game closet from the townhouse in “The Royal Tenenbaums”? That idea is back too, says Gachot. Last year she designed an epic game room backed by a rock climbing wall for a young family in Montana.
When you’re watching a show or on your phone, “it’s a solo experience for the most part,” the designer said. “The family really wanted to encourage everybody to do things together.”
Analog Accessories
Don’t have the space—or the budget—to kit out an entire retro rec room?
“There are a lot of small tweaks you can make even if you don’t have the time, energy or budget to design a fully analog room from scratch,” said Price.
Gachot says “the small things in people’s lives are cues of what the bigger trends are.”
More of her clients, she’s noticed, have been requesting retrograde staples, such as analog clocks and magazine racks.
For her Los Angeles living room, chef Sara Kramer sourced a vintage piano from Craigslist to be the room’s centerpiece, rather than sacrifice its design to the dominant black box of a smart TV. Alabama designer Lauren Conner recently worked with a client who bought a home with a rotary phone.
Rather than rip it out, she decided to keep it up and running, adding a silver receiver cover embellished with her grandmother’s initials.
Some throwback accessories aren’t so subtle. Melia Marden was browsing listings from the Public Sale Auction House in Hudson, N.Y. when she spotted a phone booth from Bell Systems circa the late 1950s and successfully bid on it for a few hundred dollars.
“It was a pandemic impulse buy,” said Marden.
In 2023, she and her husband, Frank Sisti Jr., began working with designer Elliot Meier and contractor ReidBuild to integrate the booth into what had been a hallway linen closet in their Brooklyn townhouse.
Canadian supplier Old Phone Works refurbished the phone and sold them the pulse-to-tone converter that translates the rotary dial to a modern phone line.
The couple had collected a vintage whimsical animal-adorned wallpaper (featured in a different colourway in “Pee-wee’s Playhouse”) and had just enough to cover the phone booth’s interior.
Their children, ages 9 and 11, don’t have their own phones, so use the booth to communicate with family. It’s also become a favorite spot for hiding away with a stack of Archie comic books.
The booth has brought back memories of meandering calls from Marden’s own youth—along with some of that era’s simple joy. As Meier puts it: “It’s got this magical wardrobe kind of feeling.”
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