One evening in May 2002, guests in evening dress crowded into Le Cirque 2000’s red dining room in midtown Manhattan's Palace Hotel. The unofficial VIP space in the storied restaurant’s second New York location featured a lurid explosion of heavy silk brocade, red-and-gold banquettes, and fawning waiters carrying silver-covered trays.

Guests that night included chief executive officers and a smattering of A-list celebrities. Ivana Trump and her then-boyfriend Roffredo Gaetani sat at in the center of the room; a few tables over was Jocelyn Wildenstein, the billionaire-ex wife of art dealership scion Alec Wildenstein, dining with an impishly younger male companion.

Soon, Donald Trump and his then-girlfriend Melania entered the restaurant,  and guests—many of them halfway through the restaurant’s signature pasta primavera—paused to see how an interaction between long-divorced Donald and Ivana would play out.

The two managed to scrupulously ignore each other until, an hour later, when Trump paid the bill and got up. He blew Ivana a kiss, and walked out of the room.

It was just another night at the most prestigious restaurant in New York.

Fifteen years later, the restaurant, now in its third location, has suffered a series of indignities: Demoted to a single star by the New York Times, it explored offering early bird specials as it struggled to meet its bills. Often, during the power lunch hours, most of its tables remain empty. On Tuesday, it was announced that the restaurant has filed for bankruptcy. Co-owner Mauro Maccioni is adamant that his family is not closing Le Cirque but admits that if finances were better, there would be no bankruptcy. "Fine dining is not what it used to be, especially when you have a 150-seat restaurant," he said over the phone. "The recent changes to labor laws, and changes to the industry can put you behind the eight ball and we did not modify our operation fast enough."

Rise and Fall

The downfall of Le Cirque can be chalked up to many things—unsustainably high operating costs, changing restaurant trends, increasingly lackluster cuisine— but its rise and fall also track, with an almost uncanny accuracy, the shifts of New York’s real estate market.

At its height, Le Cirque was at the center of New York society when the latter revolved around the Upper East Side. When the restaurant first opened in the Mayfair hotel on 65th Street in 1974, the city’s real estate was in the midst of a prolonged slump: Neighborhoods in Brooklyn, Queens, and the Bronx were suffering double-digit declines in housing prices; Manhattan, in contrast, was experiencing a 29 percent increase in home prices, according to a 2016 report (PDF) by the NYU Furman Center for Real Estate and Urban Policy.

The so-called "Gold Coast," between Fifth and Park avenues, remained a stolid bulwark of limestone-clad co-op buildings designed for—and exclusively available to—the very wealthy. Le Cirque became the go-to restaurant for the neighborhood’s most important residents. Times restaurant critic Pete Wells, who worked as a fact-checker for Vanity Fair in the early 1990s, recalled the restaurant as a near-constant presence in the magazine's reporting. "I couldn't count the number of times I had to check the name Le Cirque," he said. “If celebrities met on the East Coast, they were at Le Cirque. If billionaires collided in the dining room, it was always at Le Cirque.”

By 1997, when Le Cirque moved from 65th Street to the Palace Hotel just below 51st Street, the city had begun to change. “In the old days, it was considered absolutely déclassé to live in a condominium,” said Donna Olshan, founder of Olshan Realty and publisher of the weekly Olshan Luxury Report. Suddenly, condos began to look appealing. “These new things being built were really beautiful from an architectural standpoint, and they had all of these amenities and infrastructure,” she said. That meant looking outside of the Upper East Side neighborhood, for the most part.

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