Aspen Has Been Overrun by Zillionaires. Has the Town Lost Its Gonzo Soul?

The death of Bob Braudis, Pitkin County’s six-term elected sheriff from 1985 until 2010, was no shock. He was only 77, but color had drained from his cheeks; he talked more slowly, breathing heavily between words; and he had begun walking with a cane. Bob was a friend, but not a tight friend. We exchanged emails over local columns I wrote, and usually talked at gatherings where we both happened to be. There was no apparent reason for feeling heartbroken, but when I heard the news I sighed deeply and rubbed my eyes to hold back tears. Bob’s memorial service drew hundreds to the Benedict Music Tent on the famous Aspen Institute campus. Nobody has that many close friends. Only those who create widespread connections attract such congregations.

Bob, a long-haired, six-foot-six gentle giant, was the epitome of an Aspen character. Joe DiSalvo, his close friend and successor as sheriff, told me a story that captured Bob’s free, exuberant spirit, from years ago when ESPN was “interviewing Aspen” to see if it was a worthy locale for the X-Games.

“Bob and I went to meet some ESPN suits at Highlands. One of the execs shook Bob’s gigantic hand. The exec asked, ‘Geez, where’d you get those hands?’ Bob replied, ‘They came with my dick.’” Aspen has hosted the ESPN Winter X-Games for two decades running.

The sadness I felt was for Bob’s death, certainly, but it was also over the loss of the wacky individualism he took from this world and, more acutely, the town. Bob was the latest on a long list of original Aspen characters now gone, from the truly famous, like John Denver and the gonzo journalist Hunter S. Thompson, to local oddballs like the serial letter-to-the-editor author Pete Luhn, who wrote almost daily, seemingly only to provoke fights with other readers, and lesser-known old-timers today immortalized by eponymous local landmarks. Puppy Smith Street is the namesake of Harold Smith, a career City of Aspen streets-department employee who once remarked to a couple of kids that the puppies they were selling for a dollar each were so ugly they’d have to pay him to take one, at which point they handed over a pup and a buck. No Problem Bridge is named for Joe Candreia, who was known for a front-yard junk collection next to his garden, where he claimed he could grow anything, “no problem.” The ski run called Felip’s Leap on Highland Bowl honors a local waiter, Henry Felip, who drove a 1948 Willy’s Jeep Truck, electing to wear goggles instead of sunglasses, and took all dares to ski any mountain chute or kayak any section of a river, which ultimately resulted in his death on a stretch of whitewater rapids on the Crystal River called Meat Grinder during spring runoff.

Both DiSalvo and his former brother-in-law, Michael Buglione, who were in the midst of a heated sheriff’s election, were at the memorial. While the two rivals appeared to be similar in their commitment to upholding Aspen’s historically progressive and humane approach to illegal drug use—which basically posits that adults can decide for themselves, we have to protect kids, and addicts shouldn’t be put in jail—the election was essentially about convincing voters who was most like Braudis. Also at Bob’s service was Mick Ireland, Aspen’s quixotic one-time-or-another mayor, reporter, county commissioner, attorney, distance runner, city councilperson, cyclist, and columnist. DiSalvo had somehow gotten crosswise with Ireland during the campaign, and the loss of his support was probably what would cost him the close election.

Slumped on my front porch that afternoon waiting out a thunderstorm, I wondered how the Aspen Times journalist Mary Eshbaugh Hayes would have viewed Braudis’s passing. Renowned for her keen observations, Hayes covered Aspen society for 45 years, until her death at 86 in 2015. She wrote about everything without aiming to please anyone. She was an Aspen iconoclast who could distinguish between phonies and free spirits. Hayes could have told me what I really wanted to know: Is anyone coming to replace the characters Aspen is losing?

Locals often say that the only constant in Aspen is change. I’ll add, mostly big change.

In the late 1800s, Aspen morphed from serene Ute hunting grounds into a booming silver-rush mining town. That era lasted only 14 years, from 1879 until silver was demonetized in 1893, yet it remains an outsize influence on how Aspen sees itself. Beginning with the mining days, Aspenites have earned a reputation for being loose, uninhibited, creative, different, or, less politely, crazy. What other kind of people would move to its harsh mountain environment and spend their days blasting and chipping through rock to, possibly, uncover enough silver to get rich or, even less likely, make a steady living? No one in the mining era expected a steady paycheck. It was strike it rich or bust!

The silver crash was followed by the Quiet Years, marked by poverty and the Great Depression and leaving only those, as my great-uncle said, “too poor to get anywhere else.” Aspen’s population dropped from around 16,000 to only several hundred. Most became ranchers and potato farmers for sustenance. Among them were the earliest relatives I knew, and I never learned what made them stick it out.

Beginning with the mining days, Aspenites have earned a reputation for being loose, uninhibited, creative, different, or, less politely, crazy.

In 1945, Walter Paepcke, a Chicago industrialist, arrived with grand ideas of fostering a mecca for healthy mind, body, and spirit, and then introducing it to America’s privileged class. Aided by the Austrian skiing great Friedl Pfeifer, Paepcke began organizing the installation of a ski lift. Lift 1, then the longest in the world, was built in 1946, not only to carry skiers up Aspen Mountain but to haul the entire town toward its modern destiny. These events also inadvertently opened Aspen up to a wide variety of kooks, fanatics, and characters—people who recognized the new ideas and ways of living that the progressive philosophy promised. These transplants were young, strong, and adventurous, giving up pedigrees, advanced degrees, careers, and any notion of a standard American life in exchange for a license to be different in this nascent mountain community.

By the late 1960s, this version of Aspen had attracted the famous, who mingled among Paepcke’s wealthy and cultivated crowd, all of them living harmoniously alongside quite a few aimless hippies. In the seventies and eighties, marquee celebrities came to town to recreate and, especially, to blend in. During high school summers, I umpired softball games where Jimmy Buffett often pitched for the Downvalley Doughboys, and the Eagles’ Glenn Frey managed the Werewolves. Jack Nicholson was considered to be more of a local than a movie star. Cher regularly teased Aspenites with her playful fashion tastes: full-length furs dragging the sidewalks, leather pants tighter than her own skin, and cowboy hats blossoming with peacock feathers. John Denver played lunchtime concerts for middle-school kids. Stevie Nicks wrote “Landslide” while vacationing here in 1974.

Celebrities still flock to Aspen, but now they seem more focused on standing out than meshing. Some locals, trying to identify the turning point, mention a very public holiday yelling match in 1990 at Bonnie’s Restaurant on Aspen Mountain, between Donald Trump and his first wife, Ivana, over his then-girlfriend Marla Maples. Now the likes of Kendall Jenner, Paris Hilton, and Justin Bieber unashamedly strike Instagram poses in popular places around town. It’s as if Aspen’s magnetism has flipped—the famous now attract regular folks.

As Hunter Thompson wrote in the foreword to Peggy Clifford’s 1980 book To Aspen and Back, which reads like a CT-scan of Aspen’s innards: “The first post WWII immigrants to Aspen were skiers from the Army’s 10th Mountain Division. … [They] came back to Aspen to live. There wasn’t much there, but they were freaks. They didn’t care about anything but skiing. Later most of them turned into fascists.” In typical succinct style, Thompson tipped his hat to some of Aspen’s earliest modern free spirits in one sentence, and in the next reviled them for eventually succumbing to the lure of real estate development money and investment opportunities.

What had made Aspenites quirky to begin with? While the town is remote and was once isolated—it’s set at 8,000 feet in a natural clearing at the end of a forested valley, walled in by majestic peaks—geography alone was unlikely to have induced the local peculiarity. The source had to be its culture, forming even before Paepcke arrived and in time spread word of mouth among like-minded people.

As Clifford astutely pointed out: “Nothing began in Aspen.” Historically, though, Aspen has attracted many seeking something different, and it has somehow nurtured them, so much so that the town still has a reputation for being flake-friendly and communally weird.

Many residents who arrived after the advent of Aspen skiing culture came running from something—a nasty breakup or divorce, a war, or the pressures and responsibilities of a “real” job. In 1955, my then 23-year-old mother drove cross-country with a friend, at a time when young women didn’t do that, to escape the long blustery winters and humid, buggy summers of the Midwest. Yes, some came for the incredible skiing, but, for many, that was just a convenient excuse.

Sheriff DiSalvo, whose office and affability lead him to intersect daily with eccentricity, recently told me, “When I came to Aspen in 1980, I was a misfit. I didn’t fit in anywhere. I found this place where that was accepted.”

Aspen’s culture of character has always influenced the way its citizens see each other. As kids, we were familiar with a local hulk of a man named Fritz Stammberger, an accomplished German mountaineer who was reputed to be an undercover CIA operative and later purportedly disappeared in the Himalayas. He was often seen on his front porch in jockey shorts, jumping up to grab the deck above him with his fingertips and knock out an impossible number of pull-ups. I’ll never forget spotting him charging up the Ridge—terrain that rises under the Bell Mountain chairlift—in the middle of a January blizzard, shirtless, gloveless, with skis flung over his shoulder and steam billowing off his torso. We did not see him as an odd duck. He was just one tough local dude.

In recent years, Aspen has changed significantly yet again, along with resort towns everywhere. During the pandemic, massive federal stimulus money was disbursed widely, and much of it was spent on prized residential real estate investments. At the same time, wealthy white-collar workers, able to do their jobs remotely, could not get away from the COVID-19 lockdowns in cities fast enough, so they literally headed for the hills. With the effects of global warming accelerating, even more people with means continue to eye this protected perch in the cool mountain air.

The pandemic, economic policies, technology, and climate change have combined to make housing costs skyrocket, even higher and faster than they had already been doing since the 1980s. Before that, almost all of Aspen’s workforce lived in town. In the mid-eighties, increasing numbers of construction workers began commuting into Aspen from downvalley communities like Basalt and Carbondale, places where there was more land to stage their businesses. As Aspen housing costs rose, lower-income worker migration to those towns became middle-income manager migration. By the nineties, young professionals were seeking downvalley semi-affordable family homes. Today less than 30 percent of Aspen’s workforce lives in the town, and most of these residents bought in years or decades ago. Many young working Aspenites continue living with parents even after graduating from college.

Other results of astronomical housing prices have been an accelerating exodus of aging locals, forced out or cashing out of historic ski towns, and the loss of young seasonal workers, who are scared away by the near impossibility of finding a place to live. I’ve heard anecdotally about these forces draining community personality from places like Vail and Sun Valley, and I’ve seen it clearly in Aspen, the town of my birth. The souls of ski towns are changing.

Today, locals frequently worry that Aspen is losing character. More than any man-made amenity or setting of inherent natural beauty, this intangible attribute is what brings the town’s mind, body, and spirit to life. It is difficult to predict what the loss means for the town’s future. It may be only that locals feel the familiarity slipping from a lifestyle that was their passion. Or this period of unease may mark a profound transformation of authentic ski towns like Aspen into controlled, resident-free resorts, like Disneyland.

To answer the question of whether Aspen is still an offbeat town filled with characters, it’s necessary to try defining what a “character” means in the collective mind here.

To this end, I sought out Daniel Joseph “D.J.” Watkins, author, producer of the film Freak Power (a 2020 documentary about Hunter Thompson’s famous 1970 campaign to become sheriff), curator of Thomas W. Benton’s gonzo art, and an astute observer of Aspen’s history as a counterculture incubator. I asked him if a character can make it in ultra-expensive Aspen anymore.

“Bob Braudis told me that to live in Aspen today, you have to figure out how to live off the breadcrumbs of the rich and be able to pick them up without losing your dignity,” he said with a laugh. “All the rich people who came to town wanted to meet Bob. They knew we were friends. I’d say, ‘Sure, bring me an envelope with two thousand cash in it, and I’ll arrange a lunch.’ It paid Bob’s rent.”

The price tag on an average Aspen home is a staggering $13 million. Some might claim anyone willing to pay such a price for a middling house is nuts by definition.

It’s not that gonzo characters can’t be wealthy. Aspen has embraced many people like this—Walter Paepcke quickly comes to mind. So does Nick DeWolf, an early computer genius who, with Travis Fulton, in the mid-1970s programmed the landmark downtown water fountain that never repeats its pattern, and who installed a bright yellow planetarium and telescope dome on the roof of his lavender Victorian house.

Things have changed noticeably, though. A November 2022 article in The Wall Street Journal called it the most expensive town in America. The price tag on an average Aspen home is a staggering $13 million. Some might claim anyone willing to pay such a price for a middling house is nuts by definition. But even if nonconformists are equally distributed throughout the socioeconomic classes, only the super-wealthy can afford to live in Aspen now. In and of itself, this is homogenization.

Workers in Aspen’s hotels, restaurants, and shops have historically struggled to make ends meet, getting by on wits and will. It used to be that you didn’t always know or care where people lived, or if they worked, much less whether they were rich or poor. Today, it’s a given: if you’re a newcomer, you have money. Even many doctors and attorneys can’t afford Aspen. Many wonder who will replace the aging professionals who arrived years ago, when housing was still a possibility on their six-figure salaries. Professionals now eye mid- and downvalley offices and homes and require Aspenites to travel 20 miles or more for their services.

The percentage of Aspenites over age 65 has more than doubled since 2003, to 15.2 percent. Meanwhile, the average age of skiers and snowboarders in the U.S. jumped from 26 to 33 between 2005 and 2020. Psychologists generally agree that creativity peaks by early middle age. Studies confirm that we typically take fewer risks as we get older. It’s documented that humans become calmer and more emotionally stable later in life. In short, advancing age does not usually sustain nonconformity.

Many characters on the Aspen scene today came before the advent of concerted efforts to brand the town as “Aspen.” But the place’s image is not fashioned by creative wanderers anymore. Market surveys now direct it. Aspen no longer throws up an invisible middle finger to take us or leave us; it now alluringly waves manicured hands at those who can pay the price to come closer. If Aspen’s quirky reputation remains, it is projected by people in business suits on Madison Avenue rather than ski bums pedaling bicycles in ski boots up Mill Street to the slopes.

Currently, the Aspen Ski Company is pushing its new ultra-luxury brand, AspenX, to sell an image and product line appealing to the highest-net-worth individuals. These people won’t be sleeping on somebody’s couch like ski bums in the seventies. The hope is they will snugly settle into a suite at the Little Nell for around $2,500 a night. The program was hastily unveiled last spring and spun as a plan to harmoniously meld the “duct tape” (i.e., local) and “diamond” (visitor) crowds. The duct-tapers were derisive and incredulous: Is this a joke?

I asked DiSalvo a loaded question: Are the ultra-wealthy drawn more by Aspen’s real estate potential or its wild reputation? He replied, “Neither. It’s safety. Nobody’s getting kidnapped. Nobody is getting robbed. The schools are safe. Your kids can get on the bus and go to the movies, and you don’t have to worry. The new Aspenites think they’re characters if they stay out past midnight.”

In this time of unease in the world, no reasonable person should begrudge rich people seeking security for their families. Still, when everyone is coming to Aspen for safety, that further dilutes the diversity of personalities.

I tweaked the question for D.J.: Do wealthy newcomers appreciate Aspen’s characters?

He chuckled. “Naw. …They probably feel better about themselves without somebody cooler than they are around.”

In October, I crewed for family and friends in the local Golden Leaf Half Marathon, which is run through the woods between Snowmass Village and Aspen. Afterward, I thought about the time I ran it in 1984. The race was for zealots. Today, limited entry is granted digitally on a first-come basis. It’s a bucket-list event.

Sitting on the edge of the pool at the Viceroy Hotel afterward, we soaked tired legs, drinking overpriced imported beers, and tried to ignore the ostentatious velvet-covered king-size bed ensconced in an open, river-rock and fir-beamed cabana for rent by the hour, which took up an entire end of the pool deck. It was hard not to feel squeamish. Is this garish guest option the modern Aspen visitor’s idea of wild and crazy?

People drawn to Aspen today by such amenities may think they’re being off the wall, but it’s done in a contrived way. It’s like there’s a premeditated bizarre vacation behavior so cliché that it becomes a kind of conformity.

At the beginning of the skiing era, Aspenites strove to use fit bodies, uninhibited minds, and the artistic creativity unleashed by the incredible natural beauty around them to do things that few others could do—ski faster, climb higher, party harder, write and paint. Many wealthy Aspenites today strive for similar distinction just by spending sums of money that others can’t.

At the top of the Cloud Nine lift at Aspen Highlands, intrepid patrollers used to build a ski jump and launch over their patrol-shack deck while towing a rescue toboggan. In the early 2000s, the structure was converted into an upscale on-mountain restaurant. At some point, an ebullient diner impulsively uncorked an expensive bottle of champagne and sprayed it around the crowded room. That was original and borderline misdemeanor behavior.

Today, almost every day of the ski season, diners make reservations and pre-order cases of $125-a-bottle champagne, which they use to soak and get soaked. It’s been reported that one patron sprayed $17,500 worth of champagne around the room in a single “sitting.” The tiny restaurant is Veuve Clicquot’s largest customer in the U.S. Does this excess add to the Aspen legend? No. Spontaneity is gone. What’s portrayed as a wild party is thoroughly orchestrated.

A smaller Aspen was a more cohesive Aspen. In the 1960s, everyone knew the local skiing clown Ralph Jackson, who did ski ballet in a long fur coat and top hat while clenching a cigarette on a long stem in his teeth. Another character, Ralph Melville, built a quirky lodge at the base of Ajax with his own hands that, largely unchanged, recently sold for $68 million. In the 1950s, Freddie “The Fixer” Fisher was an accomplished jazz musician trusted to repair anything brought into his appliance store. In recent years, we had Benny the Blade, a Rollerblading, sunbathing, cutoff-wearing, long-blond-haired, year-round presence for three decades. I unexpectedly ran into him at the Santa Monica Pier not long ago, and he told me he could no longer afford Aspen rents.

As modern Aspen has flushed its workforce into neighboring towns, we simply don’t get to know each other as well, spending more time in our cars and managing lives spread over multiple communities. If a maverick speaks amid the din of our continual shuffle and nobody hears, did they make a point?

D.J. is an optimist. He’s weary of the doom-and-gloom talk dominating the local scene. He feels Aspen will somehow survive the billionaires too. With a flicker of hope, he says, “Maybe it’s the people who shun money who become the new characters!” Then, almost as if someone dimmed the lights inside Aspen Public House, one of Aspen’s last locals’ hangouts, he muses, “But where are they going to live?”

Characters may make us smile, wonder, and shake our heads, or they may piss us off, but for any to be authentic, the persona has to be truthful. Counterfeit insanity is on display now when people come to Aspen and want to believe in the craziness of either themselves or those they associate with. When we gaze at Aspen today, more and more often we see what we want to see or what once was. It’s just not real anymore.

When we gaze at Aspen today, more and more often we see what we want to see or what once was.

Elizabeth Paepcke anticipated the disintegration of her husband’s vision for Aspen some four decades ago. At the Aspen Design Conference in 1987, she asked the crowd: “Are we going to kill the golden goose by feeding the animal until its liver becomes distended, and we produce pâté so rich that none of us can digest it anymore? What price glory?” She concluded that Aspen “has become a town of glitz and glamour”—and said her heart was broken.

I asked DiSalvo what might save what’s left of old, quirky Aspen. “Nothing,” he said. “I think it’s dead.

“It used to be that we saw something that didn’t work and said, ‘This sucks!’,” he added. “We’ve lost our ability to say, ‘This doesn’t work for us.’ Remember the indoor smoking ban? People told us, ‘You can’t do that.’ We said, ‘Why not?’ That was 1985! We were the first place in the country to do that!”

I went into this exploration hoping to uncover a way for future oddballs and misfits to come to Aspen, to continue its tradition of sheltering a confederacy of freaks. Sadly, it seems that all paths today run through an investment bank, and new travelers are guided by a trustee. The reality pierces my heart. Aspen’s lost character is collateral damage from the scattershot of national and world events, leaving the town’s lifeblood gushing from too many wounds to stanch.

I once saw a bumper sticker in Leadville, Colorado, that said: “We’re all here because we’re not all there.” It is funny because it honestly represents many of the renegades living in that rough-and-tumble mountain town just 55 miles away, haphazardly built on the slag dredged up during the silver rush. In the moment, I envied that slogan, because at one time it would have been apt in Aspen, too. But, as nice as it might have looked on the bumper of a Saab 900 hatchback parked in front of the Hotel Jerome in 1985, it wouldn’t look right on a shiny Range Rover today. In fact, it would likely offend some who have proudly invested millions in their second or third homes here.

So if Aspen is no longer a haven for eccentrics, what is it instead? We’re all here because we’re all rich? We’re all here because, if we leave now, we’ll never get back in? We’re hanging on, hoping to win the lottery for the short supply of subsidized workforce housing? We believe in miracles? As we helplessly watch the gonzo era die, we try to figure this out. Perhaps we are all here because we haven’t got a clue about where else we would go.