Stephen McDonald ran for mayor of Jackson twice. During one of the campaigns, a debate had a Spanish interpreter.

Presumably, the idea was the candidates — native English speakers — would answer in their first language, and the interpreter would translate their answers into Spanish for Jackson’s growing Latino population. McDonald, always a bit of an iconoclast, took a different tack.

“He spoke Spanish,” said his wife, Christy. “So he answered every question in Spanish, and they would be interpreted in English.”

McDonald didn’t win either of his mayoral races, but the way he ran them indicated how he approached life. He emphasized his passions, skiing and biking, and held strong views about the community he called home after moving here in his early 20s after a stint in the military.

“We are a gateway community to the original and greatest conservation lands in the world,” McDonald told the News&Guide during his 2016 run. “We’re selling out and our visitors see that.”

McDonald died Friday on a cross-country bike trip. He was cycling on a road outside Knoxville, Iowa, when a driver swerved into the shoulder, striking him.

No charges have been filed in the crash, which is still under investigation, but the Iowa State Patrol accident report says the female driver fell asleep and drifted onto the shoulder. McDonald died on scene, according to the report. He was 52. No services are planned yet.

He leaves behind his wife of 26 years and four children, Eden, Liberty, Blaze and Damaris. In addition, he leaves a legacy of living how he wanted, as a “true skid,” as his wife put it.

It wasn’t the easiest existence, but “we made it work,” she said.

Most people pursue skiing, mountain biking and outdoor passions for a few years in their youth, then move on to whatever professional capacity defines their next phase. Not so for McDonald, who spent his years in a variety of blue-collar jobs, from driving for excavation companies to the roles he was best known for, bootfitter and mountain bike guide.

Bootfitter may not seem like an illustrious job to some, but it’s an integral role in a ski community.

“Your bootfitter is like your hairdresser,” said Anna Cole, communications manager at Jackson Hole Mountain Resort. “People have an opinion, they commit, and sometimes you have to shop around to find the right one.”

McDonald and his family were a big part of the Teton Village culture, Cole said. He was an independent bootfitter for years before taking the post at Jackson Hole Sports, and hundreds of satisfied skiers likely owe their gratitude to him.

Christy McDonald said they homeschooled their four kids so they could ski a lot, which was an undertaking and a blessing. It also made them regulars in the Village back before the era of hourlong Aerial Tram lines.

“He and his family were part of the fabric of our ski community, so it’s a sad loss,” Cole said.

For someone so well known, McDonald had a bit of a reclusive streak. He was dedicated to his family and his way of life, and that seemed to be enough.

“He didn’t have a lot of close friends,” his wife said. “I was his friend, and he met me, and he said, ‘That’s perfect, I’ll take her.’”

Still, that didn’t stop McDonald from exuding a passion his coworkers and friends picked up on. In his many summers with Teton Mountain Bike Tours, he spent days in the saddle with beginners and those who were well seasoned.

Not every guide is a good teacher, but McDonald had a way of gifting his love of the sport onto his clients no matter their skill level, said Rose Caiazzo, who guided with him for years.

“He was always so full of life,” she said, “and he would just put everyone at ease.”

To remember McDonald, Caiazzo took a ride up Cache Creek over the weekend. Pedaling up Putt-Putt gave her the time to consider the impact he had on her both as friend and coworker.

“I just kind of wanted to do that to honor him,” she said. “I learned from him in a lot of ways.”

If anything is to be taken from McDonald’s untimely death, it’s his fervor for life. It’s possible to build a comfortable life that gives a bit of your passions and a bit of other things, but it’s also possible to create something in which your passions are front and center, never more than a ski lift or bike ride away.

“He was kind of like a general,” Christy McDonald said. “He knew what he wanted, and that’s the way it was gonna happen.”

Contact Tom Hallberg at 732-7079 or

Tom Hallberg covers a little bit of everything, from skiing to long-form feature stories. A Teton Valley, Idaho, transplant by way of Portland and Bend, Oregon, he spends his time outside work writing fiction, splitboarding and climbing.

(2) comments

Raz Reinecke

I’m so glad that my husband and I got to meet Stephan after years of hearing how he was the one, the only, the best boot fitter. He had an amazing energy about him and so do his wife and daughter Liberty both of whom we met that day. Stephan and his wife had a palpable love for each other, a connection that made me think they had just started dating. My heart breaks for Christy; a soulmate like that is not someone we meet everyday. Rest in peace, Stephan. You touched so many people’s lives in a positive way.

Mark Cassen

Our hearts and prayers go out to Stephen’s family and friends, he was a star and will be greatly missed.

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