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THE NEW YORK art dealer Pat Hearn was two days away from signing a fresh lease on her gallery space in SoHo when the phone rang on a snowy Sunday night in the spring of 1994. Paul Morris, a fellow dealer who knew she was restless, suggested that they open galleries in Chelsea. “Why would I move to Chelsea?” Hearn recalled thinking. The formerly industrial neighborhood was a better place to get an oil change than to see an exhibition. SoHo was the undisputed heart of the downtown art world. But Hearn was intrigued, and she spent the next day with Morris visiting warehouses near the Hudson River. The installation artist Tom Burr, who showed with Hearn’s partner, Colin de Land, recalled her bursting into a restaurant sometime later and describing the new space she’d found: a former garage on West 22nd Street. Burr thought Hearn was crazy. “It just seemed so completely remote and inconceivable,” he said. “Going over to the Far West Side really did feel like you were traveling to the end of the earth.”

To the south was the meatpacking district, where carcasses still hung from hooks outside of the neighborhood’s namesake packing plants. To the north, 26 acres of train yards. West Chelsea was home to body shops, scrap yards, sex workers and leather bars. “In broad daylight, Chelsea is desolate; after dark, it’s downright forbidding,” New York magazine declared as late as 1996. On the decrepit freight tracks looming above the buildings near 10th Avenue, little stirred except squeaking bats. Leaking gas tanks littered the streets. “It was really scary,” said the sculptor Joel Shapiro.

Within 10 years of Hearn’s arrival, the area once referred to as Gasoline Alley would develop the densest concentration of art galleries to ever exist. By 2007, there were roughly 350 galleries packed on a stretch between 10th Avenue and the Hudson River spanning about half a mile. And then, just as quickly, it became one of the city’s most expensive residential zones. One dealer told me she sees the neighborhood as a “monument to real estate developers.” In recent years, small and midsize galleries have been priced out. Many are leaving or have already left. And dealers who spent decades in Chelsea feel a deep ambivalence toward the neighborhood — one that may reflect a more profound discomfort with the ways in which the perceived value of art and the business of selling it have transformed in recent years.

Still, Chelsea provides something rare in a city where museum admission can cost $30. Exhibitions are always free and, as some dealers note, viewers can decide for themselves whether what they’ve seen is any good. “Unlike institutions, where you go in and there are wall labels and explanations and you think, ‘That’s what I’m supposed to believe,’ you can walk in[to a gallery] without even looking if you want,” said the gallerist Andrea Rosen. Nonetheless, she closed her primary exhibition space in Chelsea in 2017, partly because the industry had come to feel more corporate than the art world she remembered.

Some of the most dramatic contrasts between Chelsea’s past and uncertain future exist on West 21st Street between 10th and 11th Avenues. A succinct history of the neighborhood is written in the buildings and voids on the block: small forklifts trundle in and out of one of the neighborhood’s last active warehouses, Kamco Supply Corp., a squat brick depot squeezed beneath the steel girders of the High Line, an elevated park on the formerly derelict freight tracks that ranks among the city’s most popular tourist attractions. The broad one-story building down the block belongs to Larry Gagosian and is one of 19 galleries in seven countries — three of which are in Chelsea — bearing his name. As much as any other dealer, Gagosian engineered the multinational model for selling art. In the middle of the block is the veteran dealer Paula Cooper, who founded one of the first galleries in SoHo in 1968, where artists like Donald Judd and Sol LeWitt showed their early work. She moved to Chelsea, converting a defunct factory with dirt floors and a dropped ceiling into an airy space with large skylights and soaring rafters, in 1996. Right next door and stretching to the corner, where the sidewalk ends in the rush of the West Side Highway, is a sprawling vacant lot, where several properties were razed to make way for a luxury complex designed by the architect Renzo Piano, complete with condos, multiple pools and new headquarters for David Zwirner, Gagosian’s chief rival in mega-gallerydom. Construction stalled in 2020 when the condo market tanked during the pandemic and has yet to resume.

Cooper is, in many ways, one of the last icons of an art world that has been mythologized as smaller, smarter, more authentic and less concerned with profit. Today, she said, “It’s just everybody out for themselves and it’s very competitive.” She was sitting in her office, at what may be one of the last desks in New York with a Rolodex but no computer. Many of her marquee artists, including Judd, the artist who designed that desk, left her gallery for international behemoths like Pace, but a more immediate threat to her business is that construction site next door. In 2018, Cooper noticed cracks appearing in the walls facing the lot. “We had to rebuild the whole corner,” she said, a process that led to a four-year absence from the space. When she returned to West 21st Street, there was a steel beam buttressing the library and a second-floor window filled in with bricks. The lot outside is still strewn with piles of rusting rebar, sheets of warped plywood, trash, gravel and tarps flapping in the rain. The developers have filed to place the property under bankruptcy protection — and recently accepted a bid on it. (Zwirner is no longer involved.) “I dread when someone starts building again,” Cooper said.

CHELSEA WAS NOT the first industrial neighborhood in Manhattan to become an arts district. In the decades following World War II, the area south of Houston Street was known as Hell’s Hundred Acres. Fires, as the name suggests, were a constant threat to workers in the crowded sweatshops, printing plants and factory lofts stacked within its 19th-century buildings. As businesses folded or shifted production overseas during the 1960s, entire floors sat empty. The city was poised to level the area, widely considered a commercial slum, to build a multilane expressway spanning downtown Manhattan proposed by city planner Robert Moses. No sane business owner would sign a new lease or make a purchase in a seemingly doomed neighborhood. Artists, however, did both. Their dealers soon followed and, in time, so did affluent residents and retail that drove away most of the artists and galleries from SoHo.

It didn’t seem possible during the 1960s, when artists began claiming empty sweatshops as homes and studios, that SoHo could change as dramatically as it did. The ceilings were high and the prices were low, but the spaces were raw. Most lacked kitchens, bathrooms and basic utilities. Making a loft livable was not only physically demanding — one artist couple hauled nine tons of trash out of a defunct zipper factory on Prince Street — it was also illegal. A surprise building inspection could spell eviction. Some residents distributed household garbage in cans throughout the neighborhood to avoid calling attention to any one corner. George Maciunas, a founder of the avant-garde movement Fluxus, planted trees in front of his building to hide the electrical wiring he’d installed.

The uncertain conditions fostered a tight-knit community and inspired rare levels of collaboration between painters, sculptors, dancers, video artists and composers. The whole neighborhood became an impromptu stage and infinite source of materials. Trisha Brown choreographed dances on the rooftops and facades of cast-iron buildings. In 1966, the sculptor Richard Serra rallied his friends Chuck Close, Philip Glass and Steve Reich to haul truckloads of rubber from a warehouse on West Broadway back to his loft. “It was like getting a grant,” he later said. A gallon of black enamel paint, the artist Frank Stella told me, cost $1 at local suppliers. Artists joined the grass-roots campaign, led by the writer and activist Jane Jacobs, to defeat the proposed expressway, which succeeded in 1969. They secured the legal right to occupy their lofts in 1971. The SoHo Cast-Iron Historic District won the protection of the Landmarks Preservation Commission two years later, safeguarding it against demolition for new development. For a time, wrote the Fluxus artist Douglas Davis, SoHo was a “forbidden zone, an artistic red-light district that scared away at least half of the affluent and commercial types it eventually seduced.”

But during the ’80s, after New York had bounced back from near-bankruptcy, SoHo began to attract more money, and more tourists. By the ’90s, one of the neighborhood’s most prominent dealers, Mary Boone, was complaining in an interview of “hordes of people” coming into the galleries. Josh Baer, an art adviser and former dealer, griped to The Washington Post about hoi polloi “carrying ice cream and asking to use the bathroom.” The art world, which has always had a reputation for insularity, had difficulty maintaining its rarefied status in the face of such rapid change. Designer boutiques began leasing ground-floor spaces, and retail giants like Banana Republic, Eddie Bauer and Pottery Barn colonized the cast-iron buildings. The influx of stores predictably drove up rents and property values, forcing artists and dealers to decamp. Annina Nosei rented the Prince Street space where she’d helped launch the career of Jean-Michel Basquiat to the Prada offshoot Miu Miu. Barbara Gladstone Gallery, which showed the maverick performance artist Matthew Barney, became a Vivienne Tam boutique. A smaller gallery, Cristinerose, transformed into an Eileen Fisher store. Chelsea may never have become a gallery district if SoHo hadn’t so rapidly turned into a shopping mall.

Nonprofits were the first cultural institutions to put down roots in Chelsea. Noise complaints drove the Kitchen, an experimental art and performance venue, from SoHo to a former icehouse in West Chelsea in 1985. The Dia Art Foundation opened a public exhibition space on West 22nd Street two years later. The remoteness of Chelsea was a natural fit for Dia, an organization known for maintaining ambitious projects in far-flung places, from the Great Basin Desert of Utah to the once-sleepy town of Marfa, Texas.

Dia became a reassuring anchor for dealers, who began visiting the West Side to see shows. At a holiday party in 1993, the dealer Matthew Marks told Dia’s then-director, Charles Wright, that he couldn’t find adequate space in SoHo. Wright recommended a garage down the block. Marks blew his savings on the building. His new gallery opened in the fall of 1994.

Marks expected that other dealers would follow, but not as quickly as they did. Hearn, Nosei, Carol Greene, Morris and Tom Healy opened Chelsea galleries in 1995. Soon, Marks was ready for a second space, and split a former cutlery factory on West 24th Street with Gladstone and Metro Pictures. At the time, one-story buildings were selling for $50 to $70 per square foot. Cooper, Lisa Spellman of 303 Gallery, the business partners Christopher D’Amelio and Lucien Terras and the couple Jessica Fredericks and Andrew Freiser followed in 1996. By July, the migration had become so conspicuous that Art Club2000, a young collective, was conducting interviews with Chelsea transplants for an exhibition called “SoHo So Long.” “I was incredibly surprised, and still am, that it’s all happened so fast,” Marks told them. “I thought, ‘Well, within five years I bet someone else will have moved.’ It was not even within five years, it was before I had even finished construction.”

For some of these pioneers, the romance of the frontier was strong. “We’re the only people who get to use an Exxon station as a deli, that’s really cool,” Freiser told Art Club2000. Greene praised the neighborhood’s “industrial qualities” and “social situation … the prostitution at night, things like that.” The position of West Chelsea, “an environment that was a bit on the margins” she said, complemented her program, which was also “pushing the edge.” Those who remember the bad old days in Chelsea sometimes describe it as barren or a wilderness. But while West Chelsea may have lacked restaurants and residents, it was hardly a wasteland; family businesses like Brownfeld Auto Service, which opened as a horse-and-buggy repair shop in the 1890s, had been neighborhood fixtures for decades. Still, the sense of apartness — what Andrea Rosen described as the incredible “nonspace” of the neighborhood — restored the otherworldly magic presumably compromised by SoHo’s crowds. Chelsea required a pilgrimage and rewarded those who made the trek with unpredictable encounters. Behind every heavy glass gallery door was another way of seeing the world.

Others saw Chelsea as a necessary move, but not an attractive one. “We had no choice,” said Wendy Olsoff, a co-founder of PPOW, a gallery championing queer and feminist artists that had in 1988 already reluctantly moved from its first space in the East Village to SoHo. By 2002, not even the unsophisticated mobs dealers once complained about were bothering to visit the remaining galleries. “We would have a show in SoHo that would get enormous press, and still people wouldn’t come,” said Olsoff. Her business partner, Penny Pilkington, kept an informal tally during the brief period when they had spaces in both neighborhoods. “I remember sitting in Chelsea and counting 400 people on a Saturday afternoon,” she said. “And in SoHo there were five.”

If the narrow, intimate streets of SoHo enhanced its bohemian aura, Chelsea, in turn, was vast, humorless and, in the words of several dealers, ugly. “I would agree that there’s something really depressing about Chelsea,” said Derek Eller, who opened his first gallery there in 1997 and is now based on the Lower East Side. “It just felt gray all the time.” Nevertheless, it had available space — and enormous garages and warehouses, as well as multilevel buildings where small galleries and artists’ co-ops could cluster together on upper floors for cheaper rents. In Chelsea, it was possible for someone young like Eller, who waited tables on his days off, to start a business. He renovated his first upstairs space by hand with a friend from art school, paid $1,300 a month in rent and immediately got coverage in The Times.

And if Chelsea was bleak, that suited the moment. The art world was haunted by the losses it suffered during the AIDS crisis. Galleries remained wobbly after a recession in the early 1990s that forced several to shutter. The apocalyptic fin de siècle sensibility “allowed people to embrace the cheerlessness of Chelsea,” said Ann Fensterstock, an art collector and the author of the 2013 history of gallery nomadism “ Art on the Block: Tracking the New York Art World from SoHo to the Bowery, Bushwick and Beyond .” The zeitgeist is what prompted them, she said, “not only to put up with the tough structures” in West Chelsea but to say, “We don’t want gorgeous columns. We want brick.”

THE CHELSEA GALLERIES grew their footprints as the art market boomed with the expansion of global wealth. Between 1997 and 2007, the number of billionaires worldwide more than quadrupled, from around 200 to almost 1,000. Western tycoons, along with new buyers from China, Russia and the Middle East, increasingly invested their wealth in contemporary art. Even during the early 1980s, when collectors had spent then-unprecedented sums on newly minted stars like Julian Schnabel during the Reagan-era stock market boom, auction records for these young artists were in the high five figures. The work of living artists only truly began to deliver exponential returns 20 years later, when contemporary art began to outsell Modern and Impressionist works at auction for the first time. In 2007, for instance, the collector Adam Lindemann consigned to Sotheby’s “Hanging Heart (Magenta/Gold),” a scaled-up valentine bauble rendered in stainless steel by Jeff Koons. Lindemann had purchased the piece in 2003 for about $1.2 million. It sold at auction for $23.5 million four years later.

The larger Chelsea galleries rose to meet the growing demand for contemporary art by opening new branches and representing more artists than ever before. David Zwirner, among the last heavyweights to abandon SoHo, made up for lost time when he arrived in 2002, establishing three Chelsea galleries in four years: large, open spaces with lots of natural light that seemed tailor-made for exhibiting art. “Try to find that anywhere in New York, or anywhere in the world in a densely populated area,” he said. The lucky dealers — those who invested early, or had the financial means to do so later — bought their spaces. Owning property, Zwirner said, “is a wonderful thing: You’re not beholden to a landlord who can just kick you out.” Soon, the supply was exhausted. “I have dealers aching to buy, but there’s nothing to sell,” the real estate agent Susan B. Anthony told the Observer in 2005. She helped find Gagosian his largest Chelsea space, on West 24th Street, a former garage that cost $5.75 million in 1999. Anthony estimated that it was worth $50 million six years later.

Chelsea “played a significant role” in the growth of the contemporary art market over the last 20 years, said Gagosian, who had moved from SoHo by 2000. (He operated a gallery in Chelsea from 1985 to 1988 but did not settle there permanently until the neighborhood had gathered some momentum.) The buildings in Chelsea, he said, allowed dealers to do “more ambitious shows,” with larger works and more of them than had been possible in the comparatively compact lofts of SoHo, where exhibition spaces were typically interrupted by columns.

By expanding both their physical footprints and their artist rosters, dealers could increase supply and bolster their gallery’s profile in a newly competitive industry. Physical growth proved especially important in Chelsea, which had become the art world’s most prominent and prestigious stage. To date, most of the artists Gagosian represents, he said, “feel that Chelsea is more relevant” and “just more part of the contemporary art world” than uptown Manhattan, Paris, Berlin or any other city with a gallery scene.

The cultural scene in Chelsea did not go unnoticed by New York bureaucracy. Whereas the architectural character of SoHo was largely protected by its landmark status, Chelsea was seen as a kind of blank slate. In 2005, the administration of Michael R. Bloomberg, then the city’s mayor, rezoned West Chelsea from manufacturing to mixed use. The decision was key to the mayor’s larger plan for the West Side, which included the developments of the High Line and Hudson Yards, the largest mixed-use private real estate venture in American history. The zoning proposal boldly claimed that it was designed, in part, to “enhance the neighborhood’s thriving arts district.”

Nothing contributed to the current tensions in that district more directly than the rezoning. Not long after the decision took effect, the real estate blog The Real Deal forecast the construction of 5,500 mostly luxury housing units in West Chelsea. “Everything is a [residential] development site, and there is not a gallery that can compete with a developer,” said one broker. A new provision allowed the owners of one-story properties under and next to the High Line, who couldn’t build upward, to sell their untapped vertical space to developers, who could use it to swell the size of nearby projects. Frank Gehry, Zaha Hadid, Shigeru Ban, Jean Nouvel and other blue-chip architectural firms conjured glass towers that turned airy streets into slot canyons. “It became kind of annoying,” said Gagosian. “There was constant noise and construction and jackhammers. You couldn’t drive down the street because it was blocked with cranes. It kind of ruined the experience of going to look at art.”

In 2011, the High Line Art program launched a series of commissions that gave artists access to a large billboard facing the park. The first installment, by the conceptual artist John Baldessari, depicted a giant $100,000 bill. The program’s curator, Cecilia Alemani, called the piece (which went up that December) a “perfect complement to the holiday season.” It was an even better metaphor for a neighborhood in which air suddenly carried a premium.

Not everyone lamented the building craze. “It made it a bona fide neighborhood,” said Zwirner, who added that while he’s “disappointed by most of the architecture,” the residential population has attracted more restaurants to the area. “When we came to Chelsea, there was one place to have lunch.” These changes hit the small and midsize dealers who did not own their spaces harder, however. “We started to get really closed in,” said Leslie Tonkonow, who could see the Hudson River from her modest sixth-floor gallery on West 22nd Street before the condos went up. “It became more difficult for a small business like mine to grow into a larger space because the real estate prices had increased so much.” Within a five-minute walk from the High Line, market values increased by 103 percent from 2003 to 2011.

Betty Cuningham was among the first to leave. The building in which she rented, valued at roughly $9 million when she arrived in 2004, sold for $160 million in 2014, the year she moved. A wave of smaller galleries showing emerging artists followed her to the Lower East Side.

Even as galleries left, developers continued to capitalize on their cultural cachet. The degree to which art became one more lifestyle amenity to rattle off in a sales pitch during this period was something new. The Getty Residences, a luxury building on the former site of a gas station, for instance, bills itself as “a work of art” and assures the prospective occupant that, by making the discerning choice to live there, “the buyer becomes the curator.” In 2009, when Tesla opened a dealership inside a former art space on West 25th Street, a representative said, “We wanted to keep the feel of a gallery.”

THE ART WORLD is an odd industry. Most other businesses prefer not to operate next door to their closest competitors, but art galleries flock together. When the most recent group of Chelsea dealers were ready to leave, they found a new frontier together.

TriBeCa, the neighborhood just south of SoHo with similar cast-iron loft buildings, has rapidly become the art world’s liveliest downtown hub. Since 2019, at least 40 galleries have opened there, including Andrew Kreps, James Cohan, Kaufmann Repetto and other Chelsea transplants. Although residential spaces there are among the most expensive in the city, ground-floor retail is relatively affordable.

On a recent Friday night in TriBeCa, a woman wearing a black tutu, clunky Mary Janes and bridal veil made her way through constellations of people smoking cigarettes and sipping cans of Mexican beer outside the galleries on Walker Street. The opening receptions for several summer shows had drawn crowds spanning several generations and scenes. A lanky 20-something with a lime green purse, long blond hair and a thick mustache who wore a sequined crop top spelling out “Grindr” over a dress shirt contemplated a sculpture made of phallic, latex-covered pillows in Chapter NY, one of the edgier galleries on the strip. The viewers were gregarious; the warm air felt effervescent. It was both entirely new and the latest chapter in a familiar cycle.

“It’s great to be in an area where midsize galleries can really distinguish themselves,” said Cohan, who moved to TriBeCa in 2019 after his Chelsea landlord announced plans to level the gallery and build a tower. Like the other dealers I interviewed, Cohan said TriBeCa feels more collegial than Chelsea did by the time he left. There are big galleries here — Zwirner and Pace have added outposts in the past two years — but unlike in Chelsea, where many megadealers own property, almost everyone in TriBeCa rents. Olsoff, who moved her gallery to TriBeCa in 2021, said it doesn’t feel as though there are “the haves and the have-nots.”

In an ironic reversal of the flight from SoHo, some prospective TriBeCa galleries are taking over clothing stores. The Chelsea dealer Alexander Gray is currently renovating a former sportswear shop in what was originally a manufacturing building on Broadway. I asked Gray if he worries about losing this space when his lease is up in 10 or 20 years. Is he worried about the galleries moving on; about having to do it all over again? He paused before replying, “Is acceptance the same thing as worry?”