Same Jackson Hole ski bum, different day
01 Mar 2022
From “genetic ski bum” to “earned ski bum”
Winter/Spring 21-22
Written By: Lexey Wauters | Images: David Bowers
If Jackson can boast a quintessential “mountain culture” — which it can — then surely Benny Wilson is one of its cultural icons. For a particular subgroup of ski bums, Benny represents the mythical past and the authentic and burly present of Jackson Hole.
Benny laughs when I ask him about the early 1970s ski bum culture. “Are you kidding me? It’s just what we did!” he says, recalling his posse of Teton Village kids — known as the Teton Village Mafia — who would wait anxiously for winter storm days when the school bus just didn’t show up. “It was a long way to town back then,” he chuckles. He also remembers the Village’s adult ski bums — hotel employees who lived on site and ski area workers who lived in the three-story bunk house known as The Chalet. “Us kids thought they were the guys to follow around. Our parents saw them as child care.”
Like many of his friends, Benny quit the ski life when he graduated from high school. He spent some time in Laramie, attending the University of Wyoming, and put in three years with the Marines. When he left the military and reviewed his options, he decided he would head back to the mountains and give the ski bum lifestyle a second go.
Benny landed back in Jackson Hole and started making ski videos. He worked for Howard Henderson with luminaries like Dave Miller and Jon and Rick Hunt and skied with a new posse — skiers who came from resorts like Mad River Glen and Sugarloaf to ski “The Big One.” They worked as dishwashers and servers and drove snowplows to feed their ski habit. Skiing “between the lines” (inside ski area boundaries) was completely optional. (Poaching, skiing outside ski area boundaries, wasn’t legal then.) When asked, Benny scoffs, “Poach- ing? We all poached — every kid, every ski mechanic, every bartender.” Benny explains that camaraderie and community was built on the tram dock; the same faces would be there every morning. Benny called the group the Jackson Air Force and designed patches on a cocktail napkin. The patches were awarded mysteriously and surreptitiously and became highly coveted, as they are to this day.
Benny made the transition from “genetic ski bum” to “earned ski bum” (his terms) in 1992 when he joined the ski school. He says that teaching skiing was a natural progression. “I mean, I was good at it, why not make a living at it?”
Why not indeed? Though many of his days are spent in a red coat skiing with clients, Benny still dons his trademark jean jacket and rips one somewhere beyond a rope line. He smiles when he admits “sure, it’s a career. It’s also the job that I have so I can go skiing every day.”
The Teton Village Mafia would be proud. 
