Adam Hay-Nicholls

Ever been barked at or serenaded on an Aspen ski lift? You might just have encountered one of the resort’s notorious ski gangs, writes Adam Hay-Nicholls.

Like West Side Story’s Sharks and Jets, but on skis, the ritzy American resort of Aspen has its very own gang culture.

When settling into the Silver Queen Gondola lift that takes winter sports lovers from the town’s East Dean Street and the five-star Little Nell hotel up to the top of Aspen Mountain, a ride soaring 995 vertical metres, don’t be surprised if a bunch of skiers burst in barking like Rottweilers, or start serenading you with some Marvin Gaye. And when you get to the 3,414m summit, good luck in trying to keep up with them on the way back down. You just encountered one of Aspen’s notorious ski gangs, a counterculture dating back to the early 1970s.

The Flying Flynns, the Bell Mountain Buckaroos and the Dogs were among the first posses on the scene, forming in 1971. The ski gangs are tribes, like college fraternities, each with their own reputation. Unlike urban gangs, ski gangs share the same territory – in this case, 675 acres of steep spruce-bordered runs.

There are more than a dozen different gangs, some with members now in their 70s while others are in their 20s. They are kindred spirits brought together by their desire to ski with the best freeskiers during the day and rage in the bars late at night. They also appear to have Peter Pan syndrome, where boys want to stay young forever. One member will text the group, suggest a meeting at the lifts, and off they go to make tracks in fast, flamboyant and often synchronised style.

Local blogger Andrew Israel, 63, says the gangs “are all about skiing and the bonds of friendship”. Co-founder of the Buckaroos, Mark Hesselschwerdt, an athletic 72, explains that his clique was brought together “by a love of skiing and pot. Looking back, that was the glue that held everything together.”

Most of the ‘gang-bangers’ were schooled at Aspen High. Others came from elsewhere. Driven by what the gonzo journalist Hunter S Thompson (a long-time Aspen resident and one-time candidate for sheriff) termed ‘Freak Power’, the Colorado enclave attracted young Americans tired of the Vietnam War and ready to embrace free love, psychedelic drugs, and living on the fringe. From then through to the present day, Aspen has become the Rockies’ capital of skiing and partying.

As Aspen’s star has risen, so too have the prices. The Kardashians and the Obamas are frequent visitors, as are an army of Wall Street bankers. Jeff Bezos is known to eschew ski days for downtown shopping sprees… on horseback. Waiters and ski instructors regularly earn $1,000 tips. At the Cloud Nine mid-mountain restaurant, by the end of each season, 1,000 cases-worth of Veuve Clicquot will have been squeegeed off the walls.

The ski gangs are a counter-point to all that, though it was three rich guys who kicked off the culture and had ski bums following them up the mountain like the Pied Piper of Hamlin. Fifty years ago, oil tycoon brothers Jack and Don Crawford arrived from Southern California, hosted the best parties Aspen had ever seen and inspired a ski hard, play hard attitude. The third mover and shaker was millionaire Denver attorney Gene Reardon, known as ‘Chief’ because of the long headdress he would sport after sundown. He was a man who appreciated the finer things: fresh snow, vintage wine and Scandinavian fashion models. The ski bums were in awe.

Nevertheless, there’s always been a strong anti-bourgeois streak that characterises the ski gangs. The Flying Flynn’s clubhouse was called The Buffalo Club, poking its tongue at the exclusive Caribou Club. The ‘Flyers’ were considered more white collar than some of the others. The Buckaroos were the most open of the gangs, welcoming anyone who wanted to ski with them. The founding members were ski instructors. They had a reputation for success with the most beautiful girls, and had the best singing voices, which became their calling card on the lifts.

The Dogs were the most gruff and anti-establishment. If the Buckaroos were the Beach Boys, the Dogs were the Sex Pistols. Andrew Israel recalls his first run-in: “I was getting on one of the gondola cars, and these three guys started going ‘woof woof’, kinda aggressively. I didn’t want to get on. I took the next one. I asked the lifty ‘who were those a-holes?’ and he said ‘those were the Dogs’”. Israel would go on to join the Buckaroos. “The Dogs tend to scare away outsiders, whereas the Buckaroos like to meet new people.”

Every year on closing day in April, at 1pm, all the gangs – a hundred people in total – meet for The Buck Off, aka Rumble on the Ridge. “We ski down the ridge of Bell. It’s a very steep double black diamond run,” describes Israel. “It’s not really a race, it’s just to see who skis the hardest.”

The gangs aren’t the sole preserve of men. Some are mixed, while female-only crews include the Powder Sluts, Chicks on Sticks, the Menopausal Mamas and, of a younger generation, the Lady Creeps. New gangs are encouraged because people joke that the dogs didn’t have puppies, and Israel reveals the Buckaroos were also “very bad at reproduction. Barely any of us have children.”

Of the millennial ski gangs, The Freaks are universally considered the fastest. Three of their dozen or so members have been professional skiers, including Olympian Wiley ‘Danger’ Maple, and they’re all in their late 20s and early 30s. They usually wear all black and they never wear helmets.

“Among our group are lawyers, an architect, an accountant, teachers, but most of us have a racing background,” says Maple, who started skiing aged one-and-a-half and was representing his country at 18. “A few of us started skiing together when we were young and we never stopped. It’s just a laugh, and we don’t have any rivals cos we’re the best.”

The Freaks’ name was inspired by Hunter S Thompson. “He hated to see the way Aspen was becoming an establishment destination,” says Victor Major, who works in marketing. “We relate to that, and his love of Aspen. It’s getting more ritzy here every year. You can see that in the real estate prices. But there’s still a core community here. The Freaks represent them and not the second and third home owners.”

Among the gangs’ meet-up spots were the Red Onion saloon, a holdover from the silver mining days, and the Skiers Chalet, which hosted Cary Grant and Jack and Bobby Kennedy in the 1950s, but which has grown dilapidated. Here, ski bums shoot pool, play beer pong and smoke pot (which is legal in Colorado). Of the 11 rooms, only seven are in a fit enough state to rent out, but the rent is cheap. However, the hotel was recently sold for £16 million and is slated to be knocked down. The Red Onion hasn’t reopened since Covid lockdown. Could the gangs be facing extinction too?

“When I got here, there were a thousand kids running around the streets trying to get laid. The war had just gotten over, people wanted to be ski bums,” says Hesselschwerdt, a handyman who has earned an honorary doctorate in Gravity from the local college. “It’s basically a retirement village now. It’s crazy that kids are still coming to be ski bums, because there are so many easier places to do it. It’s tough to find housing here.”

Sixty-year-old Mikey Wechsler, who used to work at the Red Onion and is the youngest of the Dogs, says “it’s all about the money now. People see Aspen as a commodity, not a community.”

Dr Thompson wasn’t a ski bum himself. “He only went up the mountain once in his life,” laughs Aspen realtor Tim Mooney, a friend of the deceased writer. “He had such a trauma coming back down that he had no appetite for skiing after that. But Hunter’s Freak Power movement was saying you could be both an intellectual and a freak, and The Freaks live up to that label. They’re young, hot and enlightened, and they live for big air.”

The mountains that make up Aspen Snowmass are home to over 150 homemade memorials; sanctuaries hidden in the spruce trees and lodgepole pines which are dedicated to beloved locals, artists, musicians, cowboys and even cartoon characters. In addition to Elvis, Jimi Hendrix, Marilyn Monroe and HST is a shrine to Sam Coffey, the ringleader of The Freaks, who died unexpectedly of a stroke in 2019 aged 29. Hugely popular, Coffey had a realistic ambition to become mayor of Aspen. His sister has since joined The Freaks and now lives at their 150-year-old clubhouse, dubbed Freak Mansion.

To immortalise Sam on the mountain, the crew have hung photographs, his ski equipment, and other keepsakes in the trees at Richmond Ridge, his favourite spot. One of The Freaks’ three snowboarders, Oliver Bacharach – who despite being the son of songwriter Burt Bacharach chooses to wait tables at a downtown restaurant – helped to make the shrine for his friend. “We keep adding to it. I do a bit of stained glass and made a little piece for it, although stained glass mightn’t last that long up there. We also made a swing using half a beer keg as a seat. Sam loved to drink Coors.”

“We go and visit Sam, take in the view and ski back down Kristi’s, the steepest run on the mountain, blasting from mogul to mogul until we reach the bottom,” says Major. “That’s what gangs are all about; skiing with your friends, loving Aspen, and making the most of every second we have.”