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How Dan Brodsky’s reputation and status secured the Flatiron building

Rich Brockmann - The Real Deal

Decades of civic leadership conveyed stature to complement deep pockets

The 2,000-year-old ruins of the Temple of Dendur — the pride of the Metropolitan Museum of Art’s Egyptian collection — provided the backdrop for the movers and shakers who got together last fall for real estate’s version of the Met Gala.

It was a Who’s Who of people holding the kinds of status symbols envied by the merely rich as they strive for the upper echelons of high society.

There was Amy Rose, head of the developer Rose Associates, whose family name hangs over the Rose Reading Room at the New York Public Library on Fifth Avenue. Bill Rudin of Rudin Management, whose father has a corner of Park Avenue named after him, is a gala regular. There was Related Companies President Bruce Beal, a scion of one of Boston’s most influential families. And then there was Dan Brodsky of the Brodsky Organization, one of the city’s biggest residential developers and most influential civic figures, who has, relative to his peers, avoided the limelight.

With several hundred of their colleagues, they donned their tuxedos and evening gowns for the annual fundraiser hosted by the Met’s Real Estate Council, where tables cost as much as $100,000 a pop.

The night’s cultural offerings included a viewing of the museum’s exhibit on French modernist painters Édouard Manet and Edgar Degas. But for some, patronage of the arts was just pretext: Several VIP attendees admitted they skipped the masterworks and spent the night back-slapping with friends and gossiping about their latest deals.

The yearly dinner is a highlight for Brodsky, longtime head of the Real Estate Council and former Met chair, who may have had the biggest deal of the night to talk about. Two days after the event, he announced that his company had come in as peacemaker in a power struggle for control of the iconic Flatiron Building. The drama had gripped the industry all summer. Brodsky had come up with a solution that satisfied the needs of the various stakeholders and would be taking the lead in converting the landmark into condos.

“Dan was the solution,” said one person familiar with how Brodsky won the deal, the details of which — told here for the first time — reveal how he’s operated as one of real estate’s most influential leaders.

In addition to leading the Brodsky Organization, he is on the executive committee at the Real Estate Board of New York and spent 10 years as chair of the Met — arguably the most important society position in the city. He has sat on the board of almost every private school that matters (Riverdale, Brearley, Dalton, St. Bernard’s and Trinity) and is even president of his co-op building on Park Avenue — the kind of address where outrageous wealth alone isn’t enough to get past the discerning board.

For all his achievements, Brodsky has remained relatively low-key, especially compared to public-facing contemporaries like Donald Trump and Larry Silverstein. That has so far left the story untold of how he created a kind of aura around the Brodsky name over the past five decades — using his deep pockets, cunning dealmaking and the right connections to amass the kind of power that money alone can’t buy.

“He’s shrewd and he’s wealthy,” explained one person who’s seen Brodsky in action.

Radical chic

Brodsky, 80, with feathery white hair and a blue-blooded demeanor, looks like something out of central casting for a show about prominent New York real estate families.

His grandparents came here in the early 20th century, he noted at a press conference last winter with Mayor Eric Adams, where he was helping provide resources for asylum seekers arriving in New York. “Our nation and our city have always been improved by immigrants,” explained Brodsky, who declined to be interviewed for this article.

Morris and Bella Brodsky emigrated from Russia and settled in Hell’s Kitchen, getting by as tailors. They had a son, Nathan, who served in the Navy in World War II and began buying up and renovating old apartment buildings and hotels in the West Village in the 1960s.

This was where Nathan’s son, Dan, grew up. His father enrolled him in the Little Red Schoolhouse, the private school famous for its left-wing politics and alumni who include Angela Davis and activist Tom Hurwitz.

“He grew up in the Village with these liberal — I’d say almost bordering on radical — politics,” said TF Cornerstone’s Tom Elghanayan, one of Brodsky’s longtime friends. Amid the counterculture, Brodsky began to shape his worldview.

“He’s always been big on giving back. He’s kind of like a limousine liberal in that way,” Elghanayan added, using the term as a compliment.

“I think people mistake calm, thoughtful decision-making without bravado for passiveness.They don’t recognize there’s power in a different style.”

Nothing quite embodies that tension between privilege and obligation to those less fortunate like Brodsky’s home, 895 Park Avenue. He lives in the tony Art Deco co-op with neighbors like fellow developer Daniel Rose, Tisch family scion Andrew Tisch and former Goldman Sachs CEO Lloyd Blankfein.

The building’s most famous resident was the composer Leonard Bernstein. In January 1970, Bernstein hosted a fundraiser for the Black Panthers in his duplex penthouse — an event that was immortalized by Tom Wolfe in his essay “Radical Chic.”

Bernstein, Wolfe recounts, put into words the dissonance between the politics of this Park Avenue set and their home.

“‘When you walk into this house, into this building’ — and he gestures vaguely as if to take it all in, the moldings, the sconces, the Roquefort morsels rolled in crushed nuts, the servants, the elevator attendant and the doorman downstairs in their white dickeys, the marble lobby, the brass struts on the marquee out front —‘when you walk into this house, you must feel infuriated!’”

“So you’re going to start a revolution from a Park Avenue apartment!” Bernstein summarized.

895 Park is exclusive, the kind of building where money by itself isn’t enough to gain entry, where the board will only approve buyers with a certain pedigree. Sitting atop that board as president is Brodsky.

Another box on Brodsky’s society checklist is his art collection. He and his wife, Estrellita, have been named among the top 200 art collectors by

Estrellita (descendant of a Uruguayan president from the late 1800s) is an accomplished scholar who focuses on Latin American art, while Brodsky favors works by the mid-20th-century architect and artist Le Corbusier. The two were married in 1975 at a ceremony at Temple Emanu-El, the seat of the Upper East Side Jewish community, and run their own art space in Chelsea, bolstering their art scene credentials.

Brodsky had been involved with the Met through the Real Estate Council since the 1980s, and in 2011 was elected as chair of the museum.

It was a time of challenges for the Met. Early in his tenure, the museum began running a budget deficit and had to make cutbacks. The museum’s chief executive resigned under pressure in 2017, and the board took the unusual step of reorganizing the leadership structure. Critics saw the move as prioritizing fiscal responsibility over artistic control. The museum faced other troubles, including an affair between the former CEO and a staffer and controversy over stolen art that swept through many institutions at the time.

It’s difficult to tell where Brodsky sat in all of this. When news of the staffer affair broke, observers told the New York Times that Brodsky was a “likable but passive leader who avoids conflict” and carried on the tradition of Met chairs keeping the larger board mostly in the dark on major developments until the last minute.

Candace Beinecke, a corporate lawyer at Hughes Hubbard & Reed who took over as co-chair in 2021 when Brodsky stepped down, said she didn’t think that was an accurate description, though she acknowledged that Brodsky is not the archetypical alpha-style leader who governs by force.

“I think people mistake calm, thoughtful decision-making without bravado for passiveness,” she said. “They don’t recognize there’s power in a different style. If you expect a screamer, that’s not Dan. He’s a humble person, but he’s not a passive person. There was no decision he didn’t confront.”

Brodsky’s legacy with the museum during his 10-year term included the redesign of Koch Plaza on Fifth Avenue, adding Islamic galleries and the Costume Institute and replacing 30,000 square feet of skylights, according to Met spokesperson Ann Bailis.

“Brodsky oversaw many acquisitions and significant gifts, most notably the transformative gift of Leonard Lauder’s Cubist art,” Bailis wrote.

Of course, a passion for art and devotion to the institution aren’t enough to get the highest seat. One of the major qualifications is that the chair is a proficient fundraiser expected to lead by example.

To that end, Brodsky has donated more than $20 million to the museum since 2001, according to tax filings for his and his wife’s charitable trust.

Flatiron fracas

“Get ready for the fucking lawsuits,” a man yelled outside a Lower Manhattan courthouse last spring at the second attempt to sell the Flatiron Building — an affair people followed like a piece of prestige drama airing Sunday nights on HBO.

Then Brodsky calmly plotted the series finale in his distinctive style.

To recap: The aging landmark had been sitting vacant, stuck in a state of inertia as its owners squabbled over control. A group led by Jeff Gural’s GFP Real Estate owned the property alongside investor Nathan Silverstein through a structure known as a tenancy-in-common. It required everyone (regardless of their economic stake) to agree on major decisions, and the owners just couldn’t get on the same page.

After years of fighting, they finally agreed to offer the property up last March through a process known as a partition sale. That turned into a circus when a mysterious outsider named Jacob Garlick bid $190 million, which it turned out he did not have.

A month later, Gural won the repeat auction with a bid of $161 million. But the saga wasn’t over, and the next interlude was filled with drama, previously unreported, according to sources familiar with the negotiations:

Before they could close the sale, Gural and his partners — ABS Partners and the Italy-based developer Sorgente Group — had to find a new investor who could meet each of their somewhat conflicting priorities.

Gural, after spending years pumping money into the property, didn’t want to spend any more and was looking for an investor who would write all the checks. Primarily an office investor, he was willing to cede control to someone with residential expertise.

“Dan was the solution.”

Sorgente, meanwhile, wanted a prominent role in the conversion so it could tout its status as co-developer of the Flatiron project to international investors as its principals sought to raise new funds.

The partners opened up the bids and whittled them down to a short list of potential partners that included Brodsky, the Related Companies, John Usdan’s Midwood Investment & Development and a partnership between Myles Horn and the private equity group Meadow Partners.

Negotiations went back and forth. One group or another would seem to have an edge on the others, but ultimately the partners picked Brodsky based on several key points.

For one, Brodsky is similar to Gural in that he invests his own family money. He can be more flexible and leave more meat on the bone for his partners than private equity-backed groups like Related and Meadow, which have to meet more aggressive return hurdles and have stricter timelines.

Brodsky was also willing to make a major concession to Sorgente. The entity created for the partnership would have three board seats, and Brodsky agreed to give one of them to Sorgente. The Italian group could then say that it is co-developer, even if Brodsky effectively makes all the decisions through the board’s majority.

Sorgente Group principal Veronica Mainetti declined to discuss the details of the negotiations but said Brodsky was always her clear choice.

“Economically speaking, their proposal was the best,” she said, “especially coming from such a tumultuous period during the partition sale. I feel so regenerated now and proud of this team and excited to finally move forward.”

ABS considered staying in the deal, but eventually opted to be bought out. Brodsky put up $40 million to buy a 25 percent stake in the building. Gural added that he has a high degree of trust with Brodsky, due in part to the fact that they’ve been close for decades.

“Most of us who are family real estate people know the other families from nonprofits and the Real Estate Board,” he said. “I was just at an executive committee meeting with Dan. We support each other’s charitable causes.”

“I can put my head down on the pillow knowing Dan will get it done.”

The luxury of quiet

Nathan continued with the family business while his son attended the University of Pennsylvania and earned a masters in urban planning at New York University. After a stint working on Gov. Nelson Rockefeller’s Hudson River Valley Commission, Dan joined his father in 1971.

It was in the 1980s and ’90s that he took the company through a boom in new construction, developing a number of large rental buildings, primarily on the Upper West Side. The Brodskys were among a handful of active builders that included Trump, who was honing his particular brand of ultra-luxury apartments.

The Brodskys were, in a sense, the anti-Trumps — focusing on more modest finishes and layouts.

They had become “masters of moderate-income rentals,” according to a 2017 paper on affordable housing from the Wilson Center think tank.

“Unlike Trump, who was pursuing superluxury finishes in his multi-building complex a few blocks northwest, Brodsky went for lower finishes and more efficient common spaces to cater to moderate-income renters,” the paper’s authors wrote.

When his father died in 2006 at the age of 89, Brodsky told the New York Times that the philosophy was born out of Nathan’s life experiences.

“He lived through the Depression,” he said. “He was afraid of superluxury because it was a limited market; he was much more interested in attracting a larger market.”

For years, the Brodsky Organization had a buy-and-hold philosophy. But history only goes so far. Dan’s nephew, Dean Amro (who appears to be following in his uncle’s philanthropic footsteps and is involved in the Met), and his two sons, Alexander and Thomas Brodsky, run the day-to-day. They have been moving toward selling Brodsky’s completed developments and recycling that money into new projects.

Work is underway on Brodsky’s latest project in Brooklyn.

The company is building a 350-unit rental building with Avery Hall Investments at 499 President Street in Gowanus. The move deeper into Brooklyn represents a new phase for the Brodsky Organization, which ventured outside Manhattan for the first time in 2017 with the purchase of the 250-unit 7 DeKalb Avenue rental tower at City Point in Downtown Brooklyn and the development of a pair of large rental buildings at Pacific Park.

In late 2022, Brodsky struck a deal to sell 7 DeKalb for $100 million to Avanath Capital Management. He was looking for a way to reinvest the proceeds, and he learned that Avery Hall’s partner, Chinese developer Gemdale, was facing financial troubles and wanted to sell its stake in Gowanus.

Brodsky sniffed out the off-market deal and put the proceeds from the 7 DeKalb sale into the project through a 1031 exchange, which allows investors to defer capital gains. The deal gives Brodsky a toehold in the hot Gowanus submarket, a rare neighborhood where you can actually build rentals since 421a expired in June 2022.

“It’s the only neighborhood where you can build rentals, and he’s getting in on the ground floor where rents will appreciate,” said a person familiar with the project.

Spheres of influence

The absence of 421a is a major obstacle for Brodsky — and a test of his influence.

It was during the early ’90s building spree that the developer established a key part of his lore as a forward-thinking policymaker.

At the time, the state’s 421a tax exemption granted a property tax abatement for a term of 10 years but had no requirement for affordable housing.

Brodsky pushed to extend the term to 20 years, and in exchange agreed to set aside 20 percent of his units as restricted-income housing — a framework that ended up being the model for affordable housing development for decades to come.

“Before that, it didn’t require any affordable [units], and that was a political problem,” said Alan Weiner, head of Wells Fargo’s multifamily lending division and longtime Brodsky friend. “Dan and I worked very closely together in the ‘90s with the city and the state to revamp the program, and then I financed a bunch of his buildings, including the first one under the new 421a.”

Whether Brodsky can revive 421a twice remains to be seen.

Real estate is pushing for a renewed version, but its lobby has lost much of its clout since the leftward shift in politics in 2019, and the industry hasn’t had luck pushing its agenda. It’s unclear what role — if any — Brodsky is playing in the discussions now.

His reputation still serves him in the industry. In deals like the Flatiron Building and the Gowanus project, when you ask “Why Brodsky?” those close to the deal are bound to bring up his reputation.

Working with family money has allowed the developer to pick and choose his projects. He doesn’t have to maintain a pipeline of developments just to keep the lights on.

But there’s something more than his track record and his fortune: Brodsky’s acquired status.

He’s sat on the right boards, collected the right art and gotten involved in the kinds of charitable causes that developers who cross over into the realm of civic leaders are supposed to be involved in.

Part of it is the idea — perhaps outdated — that the wealthy owe something to the rest of society, civic duty writ large. Dan Brodsky, remember, was the first person in his family born into money. The help comes back around.

“New York’s new socialites, in whatever era, have always paid their dues to ‘the poor,’ via charity,” Wolfe wrote in “Radical Chic,” “as a way of claiming the nobility inherent in noblesse oblige and of legitimizing their wealth.”

“New money usually works harder in this direction than old.”

Dan Brodsky and the Flatiron Building (Photo-illustration by Steven Dilakian/The Real Deal; Getty Images)