The late Aspen sun had started to set when the artist Jacqueline Humphries and the curator Hamza Walker stepped up to the gondola. They were heading to the top of Aspen Mountain. The elevation at base camp is a respectable 7,891 feet, quite high enough to make any resident of Manhattan or Hollywood a bit queasy and lightheaded, but the peak itself is 11,200 feet above sea level. That’s two miles above the ocean, or six World Trade Centers stacked end on end. A clutch of art enthusiasts, among them Walker and Humphries—an honoree at the Aspen Art Museum’s ArtCrush gala the following night—sat down in the 40-year-old gondola cabin, hanging on a wire rig ready to hurtle upward, alongside the art adviser Jacob King and one slightly altitude-sick magazine correspondent.

The gondola’s massive bull wheel spun the cabin out of the terminal and into the thinning air as Walker pointed to the door, which had not closed.

“Isn’t that thing supposed to…shut?” Humphries said.

“I can’t look down,” said Walker, the veteran curator who runs The Brick in Los Angeles, as we got higher and higher.

“I think it’s supposed to close at some point. I’ve been in these before…” I said.

The valley was thousands of feet below.

“It’s not that often someone falls from one of these things—it, like, makes the news,” King said.

“Wouldn’t it be a lawsuit waiting to happen?” Hamza said as the door hung perilously ajar, the dangling cabin throttling up the Western Slope peak with six souls inside.

Hours earlier, Humphries had been speaking on the roof of the Aspen Art Museum, engaging in some light symposia before a crowd of local aesthetes and arty folk with enough scratch and cachet to spend at least a weekend in Colorado’s ritziest slopeside village. This sort of museum programming, with an artist who had a star turn at the 2022 Venice Biennale, happens all the time at museums in major metropolises.

Aspen is not like most cities with major museums. It has a year-round population of just 6,700 that swells to only 20,000 in the high season…and at least 100 of those people are among the globe’s 2,700 billionaires. It’s not easy to get to. At Aspen’s only airport, a tiny one-runway spot that hasn’t been expanded since the 1940s, 83% of air traffic consists of private jets. Aspen is a cosseted place with manicured bushes. There was a birthday and someone ran to the local bakery—that would be Sant Ambroeus, and birthday candles were blown off its viral pink princess cake. The streets are crawling with Rivians, the hulking electric SUVs popular with the post-Elon plutocrat set.

Add all this to the presence of a Shigeru Ban–designed museum, built the year the starchitect won the Pritzker Prize. It’s free to enter, which is a gift to the community. But there’s also a good chance that the visitor can not only afford to pay—perhaps they’ve paid enough to be a trustee at one of the coastal museums serving communities of millions.

“We have some of the most sophisticated attendees, who are on the boards of major museums, particularly across the country, who have seen every show that you could possibly offer,” said Nicola Lees, the British-born director of the AAM, who’s been at the helm since 2020. “We can do things slightly off-kilter and slightly differently here, but still have a reception that puts what we’re doing alongside major exhibitions both nationally and globally.”

Hence, the willingness to blindly hop onto a precarious gondola. The door did eventually close midway up, and when the cabin landed at the peak, among the small crowd was ArtCrush cohost Jen Rubio, the cofounder of the luggage company Away, who had scaled the mountain with her husband, Stewart Butterfield, another Artcrush co-chair and the billionaire cofounder of Slack. In line for drinks was the artist Julia Chiang, fetching beverages for herself and her husband, KAWS, who was running around with their two kids. Karma founder Brendan Dugan stood with dealers such as Felipe Dmab from Mendes Wood, while Pace Gallery artist Robert Nava hiked the hill to greet artist Lena Henke, who has a show on the museum’s roof. Collector J. Patrick Collins was sitting on a folding chair next to Olivia Barrett, the founder of LA gallery Château Shatto, and Emma McIntyre, an artist who shows at the gallery. The collector Alden Pinnell, the founder of the Power Station in Dallas, had ventured up to the top too, chatting with the collectors Jason and Michelle Rubell. Whitney director Scott Rothkopf was there, as was outgoing Hammer director Ann Philbin.

“It’s so funny, it’s like everyone I’ve ever met showing up on the top of a mountain,” said the artist Jill Mulleady, who has a painting up at the museum.

Moments later, the attendees, even those in heels and slippers, were led up a hill, where a massive installation had been constructed to host Audience Plant, a performance by the artist Ryan Trecartin. Famed for his video art that presaged the fast-cut inanity and clipped upspeak that now make up social media’s lingua franca—“TikTok began in 2007 with Ryan Trecartin’s ‘I-Be Area,’” Jeremy O. Harris tweeted in 2020—Trecartin has been working out of a massive 32-acre farmland in rural Ohio, where he and his artistic partner, Lizzie Fitch, completed all the sets for the film commissioned by Miuccia Prada for her Fondazione Prada in Milan. For Audience Plant, Trecartin was on a keyboard, while on a piano opposite him was Jason Moran, the “genius grant”-winning jazz composer best known for juggling his own albums and a gig at the Kennedy Center with museum shows at the Whitney and the Walker Art Center. Trecartin told me that Moran had seen his epoch-shifting show at MoMA PS1 in 2011 and marveled at the sound design, which the artist had composed and mixed himself.

The sun had set, and it was getting cold. Trecartin’s team sold warm merch on the table, and a fusillade of free jazz washed over the top of the mountain, with Moran and Trecartin improvising ivory tinkling as a full orchestra plowed ahead on the platform below them. Atonal woodwind warbles mingled with horn bleats. The audience stayed on the top of the peak, even though there was a big gala the following night, and everyone still had to take a gondola back to base camp.

“Man, art people will really go anywhere,” one of the attendees said.

The Aspen Art Museum opened in 1979 in a decommissioned hydropower plant on the Roaring Fork River that once housed the Wild West town’s silver-mining operations—the boom that ended in the 1890s. The town was different in 1979. There was one decent inn, a boom-time holdover called the Hotel Jerome, and Hunter S. Thompson often held court at the bar in some state of intoxication with his friends in the Hells Angels or visiting dignitaries such as Bill Murray. Thompson supposedly once duct-taped Murray and threw him into the Jerome pool, nearly killing him, or so goes the legend. In 1985 the town was scandalized when a ski instructor turned alleged cocaine kingpin named Steven Grabow was killed by a car bomb outside the Aspen Club.

The Aspen of yore was an intense place to party. The museum was somewhat sleepier.

“There were collectors here and there was a museum, but it was more like a community museum—it didn’t focus on contemporary art,” said Richard Edwards, who runs leading primary market seller Baldwin Gallery, in the heart of Aspen village. “It had some contemporary art, but then it would have Eskimo snow goggles or old master paintings from Colorado collections.”

And then came Glitter Gulch. By the 1990s, the mining-town-era structures around the aging city hall had been scooped up by the gallery’s cofounder Harley Baldwin, a legendary Aspenite who decades earlier had run the campaign of the guy who beat Thompson for sheriff. The Freak Power Party had lost, the Battle of Aspen was over, and to the legendary Chivas-swilling bucket hat aficionado, the machine behind his opponent represented the death of the hippie town he wanted to build up in his own image.

“Of all the dirt pimps I’ve ever known, Harley Baldwin is the worst,” Thompson once said, according to Baldwin himself, who recalled the comment to my colleague Mark Seal in a 2003 Vanity Fair story.

Baldwin acquired the Brand Building and the Collins Block, and quickly carved out space for the retail stores usually seen on Rodeo Drive: Gucci, Brioni, Dior, Louis Vuitton, Chrome Hearts. A thriving cultural boondoggle needs contemporary art to spur on the fashion, and so the budding magnate opened Baldwin Gallery with longtime partner Edwards, a Cambridge-schooled lawyer and a then budding collector. This year Edwards, who’s run the gallery solo since Baldwin’s death in 2005, has a Mickalene Thomas show upstairs, with work by Tom Sachs downstairs, and over the decades he’s basically brought contemporary art to the entire region, importing new shows by Ross Bleckner, Laurie Simmons, and Carroll Dunham. (He also gave a number of shows to, full disclosure, my late mother-in-law, the artist Sarah Charlesworth.)

Tack the gallery on to the cultural gravitas of the Aspen Institute, which has brought world leaders, public intellectuals, scientists, and novelists to the western slope since the end of World War II. The Institute birthed the Aspen Ideas Festival, curated this year by none other than Tina Brown. The annual Aspen Music Festival draws titans of the classical world. And thus Aspen gets the urbane masters of the universe: Sid Bass, Michael Eisner, Michael Dell.

Aspen also pulled upstarts like Donald Trump, who proposed to Ivana there on New Year’s Eve 1976. She said yes. Twelve years later, the couple was back, staying at the Little Nell while Trump put up his mistress, Marla Maples, somewhere else in town. During après-ski, Ivana lashed out at Maples at Bonnie’s Restaurant at the top of the mountain and then hurtled down the slope to town, leaving Trump to clean up the mess. He just can’t quit the place: Trump is heading back to Aspen on Saturday for a $25,000-a-head dinner hosted by local backers such as mega-billionaire Jeffery Hildebrand, financier Duke Buchan III, and Fortress co-CEO Drew McKnight.

It was this Aspen—genteel but a little trashy, intellectual but outdoorsy, with the Trump-and-Ivana saga going down months before George H.W. Bush and Margaret Thatcher arrived at the Aspen Institute—that Baldwin identified and pounced on, his partner said. He even opened a private club that looks remarkably like the old Annabel’s in London called the Caribou Club and engineered it just for this mix: There’s a $4,000 annual fee for oilmen and I-bankers and a $250 annual fee for members of the volunteer Aspen Fire Department, local teachers, and the volunteers at Mountain Rescue Aspen.

“Harley was actually sort of a visionary—a lot of people think he changed Aspen, but he just anticipated the way that the wind was blowing,” Edwards said. “He saw what was happening. A lot of people were a little sad that Aspen had changed in that way, but it was inevitable. Basically every second store is a national brand.”

Flower power Aspen still lingers, from the bizarre antique shops to the “Thompson for Sheriff” posters at the dentist’s office and barbershop. Jeff Bezos and Tim Cook might be regulars in town, but at a saloon called the Belly Up, you’ll see princes and paupers alike drinking local beers and rocking out to Lez Zeppelin, the locally famous lesbian Led Zeppelin cover band.

And while we love Lez Zep and the Belly Up and Freak Power and Fear and Loathing, what’s smacking one in the face upon landing in Aspen is the dizzying influx of nouveaux riches that arrived when the pandemic led C-suiters to look beyond their park-view castles in the sky and convene board meetings remotely. Prices on the western slope skyrocketed. There were 92 homes sold for more than $5 million in Pitkin County in 2019, and 224 in 2020. Just two sold for more than $30 million that year—a report in The Wall Street Journal last year said that more than 17 homes crossed that threshold in 2022.

“The biggest change that people seem to talk about and notice are the last five years—and that is a very big change,” said Marianne Boesky, the New York art dealer with a space in Aspen. “The numbers for everything have just gone so far north that it’s changed the dynamics for the people who come here now. So you have the community that’s been here for a very, very long time, and they’re still here, and then you have this newer community that’s come in on steroids.”

Many dealers posted up in Aspen post-COVID, trying to net a whale—Almine Rech, Lehmann Maupin, White Cube. But those pop-ups are gone now. Boesky knows Aspen better than Rocky Mountain–via–Chelsea carpetbaggers. She first came to Aspen with her father, the swashbuckling go-go ’80s financier Ivan Boesky, who died in May, and who honeymooned in Aspen with Marianne’s mother in the good old days. Her parents were winter visitors, and Marianne began dabbling in summertime Aspen in the early 2010s, finding that an art dealer who knew the area could get a lot of warm-weather face time with potential clients who happened to be mondo billionaires: hiking, Pilates, hangs in town wearing shorts and T-shirts and ballcaps. The dealer closed on a parcel of land in town in 2014 and commissioned a gallery and artist housing by the famed architect Annabelle Selldorf. When it opened in 2017, blocks away from the three-year-old Shigeru Ban museum, it was something of a milestone: a major New York dealer with a no-bullshit Selldorf space in a town most people think of as a vacation place.

But then, after COVID, Aspen pads flipped at a crazy rate. The Journal reported that a house bought for $5.85 million in 2015 sold for $70 million in 2023.

“I just didn’t know what was going to happen in the universe—and it was like a labor of love,” Boesky said. “It took three years to renovate that thing with Annabelle Selldorf, just because it’s so hard to get anything done in this town.”

According to property records, the building sold in August 2021 for $6.4 million, to an LLC connected to a prominent Aspen developer, and then was resold again for $10.4 million in February 2022.The current owners are two of the co-chairs of the gala: Rubio, the Away cofounder, and Butterfield, the Slack cofounder. It’s zoned as commercial, not residential—Rubio has rented it out to Christie’s in past summers, and could work with other art organizations in the future, as it was designed as a gallery space. Plus, Rubio and Butterfield are around all the time: She and Butterfield bought a six-bedroom estate in Aspen’s Five Trees neighborhood for $25 million in 2021.

“Jen Rubio owns it now, and she’ll enjoy it,” Boesky said.

And though the Jeff Bezoses and Tim Cooks of the world curl up at Casa Tua for après-ski, that’s not who is sustaining an art world in Aspen. It’s the dedicated collectors—take John Phelan, the former managing director of Michael Dell’s investment firm, who took it to $19 billion before starting his own firm a few years ago. His wife, Amy Phelan, whom he met in 2001, spurred on their collection, and the pair made the museum’s free-admission policy possible with their (undisclosed but presumably hefty) 2008 donation. Before ArtCrush, the Phelans invited so many visitors to their home that a traffic circle snafu left their street impenetrable and their doors barricaded due to fire codes. Those who got in saw a wildly exuberant, self-consciously sexy install, with Yayoi Kusama’s floating silver balls in an indoor pool, a Walead Beshty broken-glass floor work that visitors walk, and an Ed Ruscha that puts the whole thing in perspective: Splashed across mountains that look like the Rockies, block text exclaims, “IT’S RIDICULOUS.”

Collector Nancy Magoon has a field abutting the Elk Mountains that doubles as a sculpture garden. One dealer told me that they joined a crew to go to Rachel and Ephi Gildor’s house by the ancient Independence Pass to see a James Turrell Skyspace in the optimal light. They got there at 5:30 in the morning, and they were late. Some of the foundational names of American wealth—Walton, Tisch, Bass—have parts of their collections installed in homes near the slopes.

It’s this collecting class that allows the Aspen Art Museum to be a world-class institution for a town of less than 10,000 people. There’s an innovative program in which curators work at the museum on a temporary basis, rotating in during the busy seasons. Before leaving for the Orange County Museum of Art in 2020, director Heidi Zuckerman oversaw an impressive run of solo shows in the early years of the new building: Chris Ofili in 2015, Lynda Benglis and Danh Vo in 2016, Oscar Murillo and Seth Price in 2019, with a performance by Rashid Johnson. Nicola Lees took the helm after working as a curator at NYU’s 80WSE gallery, and before that in her native London, at an institution that, like Aspen, follows the kunsthalle method of borrowing rather than collecting.

“I come from the Serpentine, so it really felt like the Serpentine of the mountains for me when I came for my job interview,” Lees told me.

This year’s group show strays from the usual art-star solo show to spectacular effect. Allison Katz, the radical painter who joined Hauser & Wirth in 2022, was given free reign to conceive of any kind of exhibition she wanted.

And so Katz went back in time to Pompeii. Each room explores the idea of public and private spaces in the ancient Roman Empire metropolis just before it was buried in fire and ashes, with the last room confronting the explosion of Vesuvius head-on. There’s some incredible paintings by Katz—surrealistic menageries of roosters and wide-open mouths and expressionist self-portraits—and an array of work by her peers and mentors: Robert Gober, Anish Kapoor, Amy Sillman, Kerry James Marshall, Karen Kilimnik. But most remarkably, she installed the works through different rooms to mimic moving through a Pompeiian house under the volcano, and even snagged some impossible-to-secure loans of mosaics from actual Pompeii. For that she can thank cocurator Stella Bottai, who, in addition to serving as a curator-at-large at AAM, happens to also curate the contemporary art program at the Archaeological Park of Pompeii.

“Every artist that curates a museum show thinks it looks like this,” said a dealer at a New York gallery on their way out.

On Friday, Katz gave a walk-through to a few writers, the artist Derek Fordjour and his wife, law professor Alexis Hoag-Fordjour, the dealer Olivier Babin, AAM curator Simone Krug, MoMA curator Stuart Comer, and others. As Katz started rattling off where the loans came from, she came to a fascinating realization. In a town where 83% of the planes landing at Aspen/Pitkin County Airport are private jets, Katz put on an ambitious museum group show made up entirely of loans that actually offset carbon emissions by taking away the need for any fuel-burning shipping. All the loans were local—save for the mosaics, which were shipped from Italy in a consolidated crate, with loan fees waived by the Archaeological Park of Pompeii and shipping costs covered by the AAM.

“We’re a non-collecting institution, so we drew on all the amazing collections down the block, which is, I guess, also very environmentally smart,” Katz said.

The Aspen Art Museum ArtCrush took place at a giant tent underneath Buttermilk Mountain. I arrived riding shotgun in a Mini Cooper convertible, Fleetwood Mac blasting, with my fellow gondola survivor Jacob King and Sam Parker, the founder of Parker Gallery in Los Angeles. It was golden hour, and the gala was golden-hour-themed. Outside, the step-and-repeat had a long, long line of people ready to have their picture taken. Inside, Sophia Cohen, an adviser to the Gagosian gallery in Los Angeles and the founder of Siren Projects, meandered by the bar, having interviewed Fordjour the day before as part of the Anderson Ranch Summer Series. She was heading to LA the next day to watch the Mets take on the Angels. Domenico De Sole, the former CEO of Tom Ford–era Gucci, strolled around with his wife, Eleanore. The artist Alex Israel was nearby, as was Serpentine director Hans Ulrich Obrist, clad in an eye-catching cream-colored suit.

“It’s from my friend Matthieu Blazy,” he said. Makes sense. Bottega Veneta was a sponsor, and Blazy’s brand parked a boutique in Glitter Gulch last December.

Shortly into the programming, Christie’s auctioneer Adrien Meyer took the stage to commence a stacked 12-lot live auction, and things started to go gangbusters, with a work by Jacqueline Humphries selling for $400,000 to a collector in the room, and Dallas collector Nancy Rogers bidding on an Israel work that soared to $265,000 and then went higher. A painting by Emma McIntyre, who became the youngest artist on David Zwirner’s roster after joining this year, was getting bid on by Gagosian director Millicent Willner. It was the first time Christie’s had been handed the gavel for ArtCrush, and it brought a battalion of senior staff, including deputy chairman Sarah Friedlander, 21st century chair head Kathryn Widing, and many others. (Sotheby’s, which had the gig in recent years, still had a robust presence, as its brick-and-mortar store stands a block from the museum.) By the time the silent auction ended the next day, $4.5 million had been milked from the proceedings, more than double what the New Museum in New York (population 8.3 million) raised at its spring gala this year, and significantly more than what MOCA in Los Angeles (population 3.8 million) pulled in.

But before everyone could depart for the after-party at the Caribou Club, and eventually depart Aspen either commercially or otherwise—a tipster spotted at least one mega-gallery dealer and their artist hopping on a PJ at Aspen/Pitkin County Airport—the honorees took the stage to give their speeches. Ban expressed his gratitude that “the people of Aspen love our building.” Jason Moran recalled coming to Aspen with his wife decades ago when she was performing in town.

“I got high—I didn’t get high that way, but I got high…with music,” he said.

And then Humphries took the stage, not 24 hours after she feared she would fall out of a gondola door, and admitted that she too had been to Aspen before, though she had only passed through and it was a long time ago.

“We came to Colorado in the summers, and it meant driving on an unpaved road, Independence Pass,” she said before the 600 people at the gala under the tent. “Aspen was a very different place then.”