'I Have Yet to Sell A Building Where I Didn't Regret Selling ': Families Forced To Sell NYC Icons

New York’s storied real estate dynasties are breaking a rule passed down through generations – never sell your buildings.

As the office market crumbles under the weight of remote work, New York families are forced to part with properties they’ve held for decades.

William Rudin, whose family helped shape Manhattan’s skyline, recently sold control of two financial district towers his family developed in the 1960s. "The world has changed," Rudin, the co-executive chairman of his family's firm, told the Wall Street Journal. "We have to take a cold hard look at our business to make sure there's a foundation for the next generation."

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The sales mark a shift for families that have weathered world wars, financial crashes and even a pandemic without letting go of their core assets. According to real estate investment firm Eastdil Secured, New York’s real estate families have sold about 10 office buildings in the past two years – double the number sold in the previous decade.

"Instead of 50 different aunts and uncles getting distributions, they're getting capital calls," Gary Phillips, an Eastdil managing director, told the WSJ, highlighting the financial strain on extended family businesses.

With a 100-year legacy in Manhattan real estate, the Kaufman family is also reluctantly selling. "We and the other families did not sell," Jonathan Iger, CEO of Sage Realty, the Kaufman family's management firm, said to the WSJ. "You see yourself through the dips and you come out – not just fine, but more than fine."

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Some families are fighting to hold on. The Gurals recently invested fresh capital into their 60-year-old DuMont Building on Madison Avenue. "It's called a capital call, which is the most dreaded term in our industry," said Jeffrey Gural, chairman of GFP Real Estate.

Despite the pain, Gural remains convinced holding is the right choice. "I have yet to sell a building where I didn't regret selling," he said.

For the Rudins, even a $100 million renovation at 80 Pine Street couldn't save it from the chopping block. "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," Rudin explained. "It became clear to us we needed to stop putting capital back into the building."

The sales represent more than just business decisions – they're the end of an era for families who built New York's commercial landscape. "When I go by 80 Pine Street, I remember the good times and bad times," Rudin reflected. "But you've got to move on."

The shift might signal a broader transformation in urban real estate, as aging office towers face obsolescence in a post-pandemic world demanding modern amenities and flexible workspaces.

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