The Death of (the Idea of) the Upper East Side

Photo: Mitch Epstein/Gallery Stock

So I was at a party on Fifth Avenue—one of those grand old apartments that represented the apex of the late-eighties Louis Quinze style. It was way over the top, and yet the vision was so perfectly realized: the quality of the furniture and the art, the proportions of the rooms, and the unity of the vision, such that I couldn’t help being blown away. It’s not my style, but I have to say it was really awe-inspiring. If the Landmarks commission ever decides to preserve interiors, this one should be at the top of the list. It was like a monument not only to a certain period of French décor but also to a recent period of haute Upper East Side life and Manhattan wealth. The dinner party was being given in honor of the Italian writer Alain Elkann. Along with Robert Hughes, who’d come in from Westchester, I was one of the few people at the gathering who’d traveled more than a few blocks that evening to attend the party.

“Where do you live?” one of the guests asked politely, trying to place me, as if I didn’t seem quite local. “The Village,” I said. There was a chorus of oohs and aahs and what-hos around the room. Then, you could have knocked me over with a feather duster, John Gutfreund, the former chairman of Salomon Brothers, said, “I want to move to the Village, but my wife won’t hear of it.”

“Me too,” said Jacqui Safra, scion of the Lebanese banking family and longtime consort of producer Jean Doumanian. “I want to move downtown, but Jean won’t let me.” (Safra and Doumanian have since put their Upper East Side townhouse on the market.) The topic became general, and debate was joined. All around me, Upper East Siders of long standing—Black Card–carrying members of the tribe that was once called the 400—followed the lead of these two Über-uptown guys and began to talk about their recent adventures downtown, about friends who’d actually made the move, about lofts with their vast expanses of wall on which to hang paintings, about how … fun it was down there. And about how expensive it had become, the last being, in this circle if I read them right, a term of approbation.

In fact, this past spring, Forbes announced that Tribeca’s 10013 was the most expensive Zip Code in Manhattan—the twelfth most expensive in the nation, followed by 10007 to the south (No. 19) and Soho’s 10012 (No. 31). Venerable 10021, which includes most of the choicest cuts of the Upper East Side, the default Zip for generations of cotillion and benefit invitations, received a national rank of No. 255. (No. 1 was Sagaponack, the former stepchild of the Hamptons. Apparently, potatoes are way up.) As recently as 1990, before the dot-com and telecom booms, 10021 was the wealthiest Zip Code in the country. The survey was based on median home-sales prices. Meanwhile, the brokerage Citi Habitats reported that Tribeca and Soho are also the most expensive neighborhoods in which to rent (average rent: $3,718 a month) followed closely by Chelsea ($3,041) and the West Village. The Upper East and Upper West Sides are bargains by comparison, with average rents near $2,500. If we broke down the figures for the real tenderloin on the Upper East Side, the three avenues between Lexington and Central Park between 59th and 96th, the real silk-stocking district, the numbers would go higher. But still, it’s hard to deny that the Upper East Side isn’t the ne plus ultra that it used to be.

Last year, I started dating an Uptown Girl, and I’ve been shuttling back and forth between the Village and the Upper East Side ever since, pondering the cultural differences between our respective tribes as well as the question of geographical determinism. Is Zip Code destiny anymore? One night, I would accompany her to the black-tie Rita Hayworth Ball; the next night, we’d have dinner at the Spotted Pig and head up to Chelsea for a nightcap and a dance at Marquee. At times, these worlds seemed bizarrely heterogeneous; but then again, Patrick McMullan was snapping pictures at Marquee or at the Waldorf, and Donald Trump was likely to be standing next to you at either venue, so it was possible to see prosperous Bloombergian Manhattan as a melting pot of sorts, for better or worse, rather than the Balkan metropolis of disparate, geographically determined tribes that I’d moved to 25 years ago. This summer, after we became engaged, these questions took on a practical urgency as we had to choose between the two realms—if they were two realms—at least in terms of a mailing address.

Going to the opera, 1941.Photo: Weegee [Arthur Fellig]/International Center of Photography/Getty Images

My fiancée is a post-deb with a venerable surname and a deep, burnished voice that sounds as if it had been passed down through many generations. So 10021-centric is she that after her first 25-minute cab ride to my apartment, she admitted that the Village was fun but complained, “It’s so far away from everything.” And on our first excursion to Rivington Street, she started to get a little nervous when she saw graffiti on the walls and sidewalks.

Many of her friends live within a few blocks of her apartment on East 72nd, and on any given night she will find some of them at Swifty’s or Doubles or La Grenouille. Her children attended Spence and Buckley before they moved on to prep school. The boards on which she serves have their meetings in the neighborhood. The Hampton Jitney stops half a block from her apartment. When we first started looking at real estate downtown, she was shocked to learn that not only wasn’t the Village a bargain but it seemed to be more expensive than Park Avenue in the Seventies, which has been the pinnacle of social aspiration for most of the past century. And she couldn’t help noticing that all the cool new buildings are going up downtown. There are plenty of crappy Bauhaus-lite towers east of Third, but anything resembling innovative modern architecture doesn’t seem too welcome on the Upper East Side—the proposed ovoid glass apartment tower by celebrated architect Lord Norman Foster on upper Madison has been opposed by the local community board; its fate hangs on a decision by the Landmarks commission and the city planning department. The announcement by the board of the Whitney Museum, that after years of struggling to gain approval for its expansion plans it would probably take its toys and move down to Chelsea or the meatpacking district, might be interpreted as a huffy slap at the neighborhood and its preservationists. No one in living memory has suggested that the Upper East Side is, or ought to be, at the cutting edge of the culture, but as the city enters a bold new era of development it risks becoming a museum of Olde New York.

Back in the days when Henry James was in short pants, New York society, such as it was, was huddled around Washington Square Park. Until the 1850s, most of the Upper East Side was common land and pastures. Central Park was completed by 1860, but no one really coveted the land adjacent to this uninhabited wilderness, and upper Fifth Avenue was slow to attract the kind of residents who didn’t keep hogs out back. Forty-second Street still qualified as uptown when construction of the Metropolitan Museum began in 1880. In 1888, upper Fourth Avenue was paved over and renamed Park Avenue, although the stretch between 42nd and 57th was still a grimy rail yard. Stanford White finished a house on Madison and 72nd Street for Charles L. Tiffany around 1885, and the cachet of the neighborhood was further bolstered when Caroline Astor had a Richard Morris Hunt château built at 65th and Fifth within the next decade. By the turn of the century, members of the 400 (the supposed number that Mrs. Astor was able to accommodate in her ballroom) like the Schermerhorns and the Rhinelanders had moved up and built townhouses in the area. Clubs like the Metropolitan, the Knickerbocker, the Colony, and the Union, which still define a certain Waspy subset of New York society, rose within a few years of each other. The Vanderbilts and Astors must have been relieved when asphalt was finally laid down on upper Fifth Avenue in 1897. Park Avenue became thoroughly fashionable after the train tracks were moved underground.

Although the Upper West Side developed more rapidly, the blue bloods moved cautiously up the East Side along the artery of Fifth. Montgomery Schuyler, the Lewis Lapham of the Gilded Age, observed that West Side apartment buildings tended toward the gaudy; Fifth Avenue, on the other hand, was the proper address for a gentleman.

Well into the twentieth century, blue bloods and their imitators lived in houses. The concept of apartment living, of different families sharing a common roof, was still wildly outré if not downright scandalous in 1912, when 998 Fifth, a McKim, Mead & White building, arose on Millionaire’s Row opposite the Met. Like all the Fifth Avenue apartment buildings that would succeed it, and unlike the towers of Central Park West, it was restrained and understated in its grandeur. Among the new residents at 998 was Levi P. Morton, who served as governor of New York as well as vice-president of the U.S. and who was one of those prominent New Yorkers whose uptown drift was emblematic. “Morton’s migrations up Fifth Avenue had always seemed to forge the way for the city’s elite,” says Elizabeth Hawes in New York, New York, her improbably riveting history of the New York apartment building. “From 17th Street to 42nd Street in 1891 (where he provided the setting in which Edith Wharton could come out more discreetly than at Delmonico’s); from there to 55th Street in 1894 … from 55th Street to 81st Street, where he forsook the genteel traditions of houses altogether.” Over the course of the next twenty years, grand apartment buildings on Fifth Avenue and Park redefined the concept of the good life. In a city that was still chaotic and dangerous, the western half of the Upper East Side, with its broad avenues and its doorman-guarded buildings, represented the equivalent of a gated community for the childbearing wealthy, with Central Park as the ultimate backyard. From that day down to the present, an apartment in one of several dozen buildings built before 1930—the number of “good buildings” is generally agreed to be 42—was necessity for status-conscious New Yorkers, as well as for those who had made their pile in Kalamazoo or Caracas and wanted to plant their flag at the center of the world. At least until recently.

Poodle-walking on Madison Avenue, 1994.Photo: Thomas Hoepker/Magnum Photos

Members of the tribe that inhabits these buildings and whose territory comprises the Upper East Side seldom use the words society or socialite, although the phrase “social people” is often used to denote its members. It is far more porous today than it was in the days when Mrs. Astor’s Patriarch’s Ball defined society; some of its members descend from those old families or newer ones like the Rockefellers and the Vanderbilts who were considered parvenus in the Gilded Age; many of its women, among them some of the fiercest guardians of its ramparts, married up from very humble backgrounds, and some of its fortunes are first-generation. It is most easily defined by the annual circuit-of-charity benefit parties, among which the cocktail preview of the International Fine Art and Antique Dealers Show at the Armory benefiting the Memorial Sloan-Kettering Cancer Center is one of the biggest. “Sloan-Kettering brings out all the Big Girls,” says a medium-size girl who is surveying the crowd on a recent October night, looking down the long aisle of antique booths at such Big Girls as Carol Mack, Hilary Geary, Pat Altschul, Somers Farkas, Debbie Bancroft, and Barbara de Portago. It is the wives (and widows and heiresses) who are the keepers of the benefit circuit, although many of the men are here as well: Ambassador Earl Mack, buyout baron Wilbur Ross, sugar heir Pepe Fanjul. It’s not a formal event, just a cocktail party, but some of these dresses and gowns could definitely go straight on to major black-tie events; observing the unwritten sumptuary law of their caste, the men are all wearing gray or navy business suits and muted ties. No one would call it a young crowd, with a few exceptions—like flame-haired model-heiress Lydia Hearst-Shaw and professional party boy Fabian Basabe. You can’t help wondering where their friends and peers are hanging out tonight and whether, when the time comes, they will bother to dress up and join the boards and carry on the arcane social-philanthropic traditions of their elders.

“This used to be so grand,” says my friend, a voluptuous blonde socialite in Carolina Herrera. “It was so great when Nan Kempner and Pat Buckley were chairing. It’s really just not the same.” This lament sounds frequently up and down Park Avenue. For many people, Nan Kempner’s death last year marked the end of a sparkling era of New York social life. The chain-smoking, best-dressing, quick-witted socialite was the embodiment of the tribe, the Platonic ideal of a socialite, the kind of Big Girl who made all the others feel good about being in the tribe, and so far she has no obvious successors. Various candidates have been nominated, privileged and fashionable women in their thirties and forties: Tory Burch, Gigi Mortimer, Marina Rust Connor, and Lauren Dupont are in the wings, but so far no one has been anointed, and it’s not clear that anyone’s volunteering. One can only imagine the fierceness of the competition back in the days when Babe Paley and Slim Keith and Capote’s other swans roamed the earth.

Donald Trump walks past, poking into a jewelry booth, his hair improbably reddish, and no one seems to notice. Trump is not a member of the tribe, although his territory overlaps theirs; he eats at the same restaurants and attends some of the signature parties. His brother Robert is a member, although somewhat less popular since he left beloved Big Girl Blaine Trump. The feeling on both sides seems to be one of indifference bordering on disdain. The Donald is unclubbable, and he’s made it clear he has no use for the genteel rituals of the tribe.

Some of the guests are examining the wares—major furniture and jewelry from the Ming dynasty to mid-twentieth century, and curiosities like an eighteenth-century walnut gentleman’s traveling case for $60,000; a carved ivory German crossbow for $220,000—while others complain about last night’s Henry Street Settlement benefit party, another major event on the circuit, judged to be overly long and boring this year. A group of women are talking about the funeral earlier today of designer Vera Wang’s father, which many of them attended. “Was there a lunch afterward?” asks one them, sounding slightly aggrieved. “I didn’t know there was a lunch.”

On this particular chilly Thursday, some of the antiques-show crowd is going on to the ‘21’ club (which wasn’t actually named after the Zip Code where most of its patrons live), where Alex Kuczynski is having a party for her book, Beauty Junkies. Not everyone approves of Kuczynski’s book, which is something of an exposé of certain tribal rituals. It would be safe to say that most of the women at the Sloan-Kettering party have been the beneficiaries—or victims—of certain cosmetic procedures, and certain surgeons and doctors are the objects of hero worship. “She’s just a total bitch for hanging herself and a lot of us out to dry,” one of the ladies who lunch griped to Liz Smith. Kuczynski is a member of the tribe by virtue of her marriage to hedge-fund mogul Charles Stevenson, though, as a working journalist, she is something of a maverick. The party at ‘21’ reflects this mix, with two fairly distinct groups, the journalists and the socialites: 60 Minutes’ Steve Kroft and his wife, Jenny Conant, crossing paths with billionaire David Koch and his wife, Julia; the two groups mingling if not quite mixing.

Still later, you will see many faces from the antiques show at Swifty’s, the modest little bistro that has replaced Mortimer’s as the canteen of the tribe. At Swifty’s, as at ‘21,’ people who fly in front of the plane or in private planes happily dine shoulder to shoulder and cheek by jowl in a space that resembles a subway car at rush hour. Up front, Kathy and Billy Rayner wave to Kimberly Du Ross, while in the tiny back room, Rand and Jessie Araskog are hosting a party for some of the patrons and committee members, and when they eventually head for the front door close to eleven, it’s like watching the clowns pour out of a Volkswagen—very expensively dressed, heavily bejeweled, late-middle-aged clowns, many of whom have their own chauffeured cars waiting outside although their apartments are only steps away. “There go the antique people,” says a young banker at my table. It takes him a moment to realize he’s cracked a joke.

It’s 10:45 on the Upper East Side. If you want another drink, then you’d best head downtown.

In a city that was still chaotic and dangerous, the western slice of the Upper East Side, with its broad avenues and its doorman-guarded buildings, represented the equivalent of a gated community for the childbearing wealthy, with Central Park as the ultimate backyard.

My dinner at Swifty’s reminded me of the Upper East Side period of my own life. Like many Manhattan-dwelling breeders, I just assumed that when I finally spawned, I would—more or less like a salmon—have to move inexorably upstream. Specifically, to the Upper East Side, for the schools. Of course, there were Collegiate and Trinity on the West Side, if you happened to want one of those particular schools, but there weren’t any restaurants to speak of back then, and I don’t think my then-wife had ever actually set foot on the Upper West Side. She was already living in Turtle Bay when we got married in 1991, more than halfway to the Upper East.

I lived then in the West Village, which I considered by far the most congenial neighborhood in the city. All the amenities of single life were nearby: bars, bookstores, restaurants, and nightclubs. There were a few kids around, most of them belonging to Brian and Keith McNally, as far as I could tell, and I was aware that St. Luke’s and Grace Church School and the Little Red Schoolhouse were somewhere nearby … but at least half the neighbors were gay men and it was basically a neighborhood where breakfast was taken at eleven and whether you liked it or not the trannies from the adjacent meatpacking district were going to use your stairwell as their place of business and sooner or later you were probably going to get mugged. These minor inconveniences notwithstanding, this was the downtown fantasy that many of us non-native New Yorkers had moved to the city in search of, the New York of the Abstract Expressionists and the Talking Heads, because we’d heard of the Cedar Tavern and CBGB. We didn’t want to be Jock Whitney or Carter Burden; we wanted to be Patti Smith or Jim Carroll.

But one day someone got pregnant. Maybe by accident or maybe after a long course of in vitro, in which case you’d probably already thought about moving uptown because that’s where most of the fertility clinics were. I convinced myself that saying ciao to the Village was part of growing up, an inevitable rite of passage, like buying a Brooks Brothers suit after graduation. It wasn’t just the schools, all the new parents ensconced in the East Seventies would tell you—it was the pediatricians and the park and the nanny network and the whole child-rearing infrastructure from Serendipity to Jacadi. This is where you inevitably ended when you started waking up at 6 a.m.—as everybody assured you you would soon be doing, once the kids came—as opposed to going to bed at 6 a.m.

If a single precipitating event can be pinpointed, the beginning of the end for the Upper East Side might be John Kennedy Jr.’s taking up residence in Tribeca. As a young man, John-John had moved first to the Upper West Side, then later downtown, not an unusual trajectory for an Upper East Side scion, even then. But when he became a grown-up and got married and still did not move back—and, in fact, displayed not the slightest inkling that he ought to or ever would—well, that suggested trouble. (It should be noted that John-John apparently did spend the last few weeks of his life, estranged from his wife, at the Stanhope, but that’s another story.)

If that defection could be explained away as an act of impetuous youth, there were others that could not, like Diane Von Furstenberg’s 1997 move from the Carlyle to a townhouse on far West 12th Street. Von Furstenberg has always crossed social boundaries, and her apartment at the Carlyle was one of New York’s great salons, the kind of place where European princesses might find themselves rubbing shoulders with West Chelsea queens; but some of her friends and their drivers must have had to get directions when the salon moved to the West Village. Charlie Rose soon became her neighbor. As the Giuliani era endured and it became clear that the citywide drop in crime was not a momentary blip but an incredible new fact of urban living, fear of those quaint but dark and unfamiliar little streets downtown receded. And then came word that renowned architect Richard Meier, who’d never built in Manhattan, was designing two residential towers along the waterfront in the West Village. While neighborhood activists rallied to fight the development, high-profile, deep-pocketed New Yorkers, the very sort who would never consider living anywhere but on the Upper East Side, started visiting Meier’s offices to look at the models and floor plans.

In the midst of my divorce, when I realized that the Upper East Side chapter of my life was over, I trooped down with a Realtor friend who had a very inflated notion of my net worth; I just wanted to see the place even if I couldn’t afford it. In the office, I shook Meier’s hand and complimented him on the beauty of the shimmering silver-blue architectural model, although I might just as well have complimented him on his own iconic, monumental appearance with that mane of silver-blue hair, since this was probably the first Manhattan building project in decades that was being sold on the basis of the star power of the architect. We then climbed back in the Realtor’s Town Car and drove to the site at Perry Street, where we viewed the fourth-floor unit in the northern tower. I was standing in a rough concrete-and-glass box with exposed wiring and, admittedly, a great river view. “Buyers get to finish the interiors themselves,” my friend informed me cheerfully. “Calvin’s going to take the penthouse. He went up in a helicopter with Richard to inspect the views.”

Nan Kempner’s death last year marked the end of a sparkling era. The chain-smoking, quick-witted socialite was the Platonic ideal of a socialite, the kind of Big Girl who made all the others feel good about being in the tribe.

The Meier project put downtown officially on the map for the uptown crowd. Many more fancy downtown buildings have been built or are in the works, bearing names like Calatrava, Gehry, Gwathmey, and Rogers, and creating a new luxury aesthetic that makes ol’ Park Avenue seem almost spartan. Despite their sometimes jarring new forms, many of the new buildings already seem to have settled quite comfortably into old neighborhoods—as any good host or D.J. knows, it’s all about the mix.

These new downtowners won’t have to travel far to visit the Whitney if the museum follows through with its plan to move its new building south. After more than a decade of trying to get approval for plans to expand on Madison Avenue, the Whitney seems to have thrown in the towel. Like some hopeful young suitor bringing one bride after another home to stuffy parents, the Whitney paraded a succession of architects past the neighbors, including Michael Graves, Rem Koolhaas, and Renzo Piano. Now, even as the Piano addition appeared to be on the verge of approval, the board of the Whitney has pulled the equivalent of saying, “To hell with Mom and Dad, we’re going to elope with a cocktail waitress.” Whatever the details of the decision, the impression seems to be that the old folks want to pull up the drawbridge and keep out anything that doesn’t look like it belongs in the 8th Arrondissement. The howls of protest that have greeted the proposal for developer Aby Rosen’s 22-story Norman Foster tower atop the Parke-Bernet building reinforce the impression that the Upper East Side wishes to be left out of 21st-century Manhattan. The community board slammed the proposal immediately, while the hearing in front of the Landmarks commission drew an overflow crowd of bejeweled and bespoke-suited protesters. William Kahn, a resident of the Carlyle House near the proposed site, compared Lord Foster’s proposal to the British occupation of New York during the Revolutionary War.

My shrink, a former student of Hannah Arendt’s, lives deep in the Lower East Side, at Houston and Avenue A, in a five-story building that has a stark, army-green, unattended, disinfectant-scented lobby. By the by, she expresses her concern and amazement about the fact that her building has been infiltrated by uptowners—a Wall Street couple and a recent college grad whose Wall Street daddy is setting her up with a nest. She is not entirely convinced that these three are good for the neighborhood that invented the slogans “Eat the rich” and “Die, yuppie scum,” which still occasionally appear on brick walls and sidewalks, but obviously they think the neighborhood is good for them. Which raises the question, when everyone and his parents move downtown, in what sense will it still be downtown? Will King Charles spaniels start to replace French bulldogs on Bleecker Street? And speaking of Bleecker, it was one thing for Marc Jacobs to set up shop there, but Ralph Lauren? Now that hedge-fund managers and trust-funders have taken over Tribeca, the former province of painters and sculptors, it may be that Manhattan geography is no longer destiny, that neighborhoods have lost their tribal signification. Or rather, the Upper East Side may be the last neighborhood to preserve its signification and its identity, if only as a kind of prewar retirement community, replete with museums and hospitals, encased in amber.

Designer Robert Couturier, a favorite of the crowd that summers in Southampton and winters in Palm Beach, has noticed a migration even among the rarefied group of his clients. “A number of older people whose children have moved away from home are going downtown. Art dealers—and, of course, the younger generation. As for the really old guard, they are staying entrenched in their Park Avenue and Fifth Avenue buildings. But what is helping kill the Upper East Side is the fact that most of the apartments are occupied by absentee owners; they are in town so seldom that the buildings look depressingly unoccupied. Whether somebody is rich in Lima, Caracas, Paris, London or Rome, Moscow or Shanghai, they all want an apartment in New York that they visit only a couple of months a year. Hence the depressing feeling that the Upper East Side is empty and on any weekend is a desert. The only thing holding many people back is the school factor.”

Even that is changing. Last year, Claremont Prep, a K-through-eight private academy, opened its doors on Broad Street in the financial district, providing an alternative for downtown parents who have been sending their kids across the river to Saint Ann’s in Brooklyn. The entire neighborhood has been reoriented. “Before, families would look on Fifth, Park, and the Gracie Mansion area and the Upper East Side,” says Corcoran broker Maria Pashby. “As recently as five years ago, families with children would tend to come uptown. No more. I just sold 31 N. Moore Street, and everyone who looked was families, families, families. With children. No single people.”

Some of those younger kids will go to P.S. 234, on Greenwich Street between Chambers and Warren, where on a typical afternoon you see almost as many dads as moms scooping up kids with Small Paul and SpongeBob backpacks. Whereas you won’t see any dads outside Buckley or Allen-Stevenson at this hour, and the mothers will tend to have a certain shade of blonde hair that seems indigenous to the East Seventies. Apparently there’s still some truth to geography; certain stereotypes endure for the moment. None of the mothers outside P.S. 234 are wearing Chanel ballet slippers. “It’s a great school,” shouts one of the fathers, an art dealer in cargo pants and a Black Flag T-shirt who is escorting his fifth-grade son to karate lessons. “The only problem is the construction noise.” We can hardly hear ourselves speak over the din emanating from building sites in the area, huge new residential towers at 200 Chambers and 101 Warren. In a year or two, his son will have plenty of new sparring partners.

In the meantime, my fiancée sweetly agreed to move downtown, becoming part of what seems more and more like a general migration. We are waiting to close on a prewar apartment in the Village, and we continue to shuttle up and down. Last night, we started at a reading and book signing in the Village, then joined another couple at Le Cirque, where we waved to at least a half-dozen of her friends, admired some major jewelry, winced at some unsuccessful surgery, and talked about acquaintances at nearby tables, people whose names regularly appear in W and Avenue and Quest, none of whom appeared to have any desire to be anywhere else.

The Death of (the Idea of) the Upper East Side