Aspen's ski gangs: Rebel guards of a culture under threat

On Aspen Mountain, there was a time when you heard singing. You heard young men harmonizing on the gondola before skiing down to the barking of another group. You would think another group was made up of all Bobs, because the guys and girls all called each other Bob.

These were some of Aspen’s early ski gangs: those singing Bell Mountain Buckaroos, those barking Dogs of Bell and a little later the Bobs.

You might still hear some of it today along Ajax, as the locals call the ski area — perhaps still along those steep, namesake slopes of Bell Mountain. That’s where the gangs didn’t so much vie for territory as much as they simply played and bonded over their quirks.

“Not quite the bloods and crips,” recalled one from back in the 1970s, “but still weird.”

Decades later, their calls are less abundant.

“It’s kind of hard now,” said Mikey Wechsler, one of the still-rabid Dogs, an avid regular and celebrated ski bum of yesteryear. “At 63, I’m like the youngest of what I guess you would say was the OG crew.”

Time has caught up to the original gangsters.

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“At the height, we could’ve had 20 people skiing together,” said Tom Egan, who arrived in Aspen in 1976 and helped form the Bobs.

Nowadays, he might tag up with two or three others from the heyday. They are no longer those wild 20-somethings venturing high for powder before lurking low to the parties that defined Vietnam-era Aspen. The Bobs came up with their name in a keg line.

“It was a fun time for sure,” Egan said of that gang era. “And it’s hard to pinpoint if and when it really died. I don’t think it died as much as it sort of faded.”

Or maybe “morphed” is the word.

Yes, gangs still roam Aspen’s slopes. Just more quietly, perhaps.

Maybe they’re not singing or barking, but they’re known to rip harder and faster than any proud Dog of the day. The Freaks — late local Hunter S. Thompson is an honorary member — are known to ski fast and tight together.

They’re not as serious as their skull-laden logo might suggest, said the local Olympian among them, Wiley Maple. “To me, it more or less just means home, good company and good fun,” he said.

Another formidable gang goes by the Umbros (related to the underwear, a member confirmed). Recent years have also seen the Flying Monkees, the Nachos and another gang of women trending to the Highlands side: Chicks on Sticks.

They can all be easy to miss, said Ted Mahon, an unaffiliated observer and local ski instructor of nearly 30 years.

“If I look around closely, I’ll just see a full gondola cabin unload with a group who are just skiing laps together,” Mahon said. “That’s how I know.”

That’s what the gangs have always been about — just skiing together, said Aspen native Jenny Harris. But it is different now, she said, in ways that are indeed hard to pinpoint.

“It’s not so distinctly defined as it used to be,” she said.

It’s not like the Dogs, who along with barking took to wearing goofy ears. They followed those singalong Buckaroos and were an “antithesis,” according to a Teton Gravity Research article that is considered the definitive history of the loose history of Aspen’s ski gangs.

The Dogs were “a big middle finger to Aspen’s establishment,” wrote Greg Fitzsimmons. He likened the Buckaroos to the Rolling Stones and Motown and the Dogs to The Clash and Sex Pistols.

Harris was raised by Dogs. Her dad, Dan, is among founding names in that article. Wechsler is another, along with the “alpha dog” he knew as his mentor: James Bond (real name).

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The gangs “were a poignant example of the infantry of skiing,” Fitzsimmons concluded. “They were on the front lines, living their passions day in and day out on the mountain, and rubbing pennies together to make it work.”

They emerged in what was a “shift” for the town, Aspen Historical Society’s Anna Lookabill Scott told The Gazette.

“From ranchers and World War II vets and kind of that dynamic,” she said, “to fairly well-educated people who are dropping out of that corporate culture and coming here to ski instead.”

They were like Egan. “I was 21, disillusioned with Nixon and the war and everything going on,” he said.

He chuckled. “Essentially what happened was the inmates took over the asylum.”

History recalls Aspen’s old guard not taking too kindly to the strange, smelly newcomers.

“It used to be, ‘No beatniks, no hippies,’” Scott said. “Then those folks who identified more of the hippies saying, ‘You can’t exclude us, you can’t make these rules against us.’”

They would make the rules themselves on city council and county commission. They would turn the focus to environmental protection, public transit and employee housing — familiar talking points today, Scott noted.

“It has changed, and it will always change,” she said. “And yet our problems are kind of the same.”

Just like ski bums of today, Wechsler back in the ‘80s worked at restaurants and roomed with others to get by on rent (he did so up until recently). But the current state of the ski bum seems different to him now — especially out of the COVID-19 pandemic, when mountain towns saw housing disparities widen with a wealthy, remote-working influx.

“I feel bad for the kids now,” Wechsler said. “I feel like kids gotta work extra jobs to afford to be here, and then they don’t have as much time to ski.”

That, he said, might help explain the changed state of the ski gangs. The Freaks’ Maple worries it’ll keep changing.

“Cost of living may eventually push out people who would normally gather together and dedicate their lives to the mountains,” he said. “It might become increasingly impossible for young people to move to town, or move back to town.”

It might already be lending to the indistinct character of today’s gangs, as Harris sees it. Take for example her “gang,” which is not really that, she said: “Just a lot of different people who were in and out of the Skier’s Chalet.”

Those are people sharing fond memories of partying at the historic lodge where resort workers lived for cheap — something of a last bastion.

Harris and her husband share those memories. They’ve been among generations bidding farewell. The Chalet is in the crosshairs of a controversial redevelopment plan.

The loss underscores a sentiment around town, Harris said: “Like we’ve lost the battle. Like Aspen has just become a resort, and that funkiness and that anti-establishment part is really just fading.”

And yet there they are, however often hard to identify: the Freaks, the Flying Monkees, the Chicks on Sticks and some unknown number of others — modern brigades of that old infantry.

Mahon, the longtime presence on the mountain, still sees them unloading from the gondola.

“We might walk through our town that we’ve lived in for a while and start to feel like it’s less recognizable,” he said. “But it’s nice to know we can always head up the mountain and connect with our friends.”

For Egan, it’s nice to spot that occasional stray Dog or Buckaroo or Bob. Recently, he spotted one of those Dogs wearing those goofy ears from back in the day.

“You just look at him and smile and shake your head,” Egan said, “and make some comment like, ‘Can you guys grow up?’”

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