Home Garden & Outdoor The Final Descent of Dean Cummings

The Final Descent of Dean Cummings

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July 1998, Aspen, Colorado

Karen Stokes knew exactly who Dean Cummings was when she met him, she just didn’t know she was talking to him. A striking blond ballet dancer and lifelong skier from Chicago, she had seen Cummings in ski magazines and movies, but he was always wearing goggles. When someone introduced them at a gear show in Aspen, Cummings gave her his card and invited her to come heli-skiing in Valdez. You’re Dean Cummings? she blushed. She’d been single for a while and was hard to impress, but they talked for hours. After they parted, she couldn’t stop thinking about him. So she wrote him a letter. He called as soon as he got it. Their first date was in Telluride at a film premiere that fall. A few months later, she moved to Valdez and they became inseparable.

Karen was 29 at the time, the youngest of seven children in a Catholic family, and Cummings was 33. They married in 2001 on top of a mountain, flying up their guests by helicopter. “It was like being in a fairy tale,” she says.

At H2O, Cummings was the big-picture visionary with charisma, while his wife, working as the CEO, was organized and patient and made things happen. They held hands when they rode in the helicopter. “He told me I was beautiful every day and meant it,” she says. They welcomed a son, Wyatt, in 2003, then a daughter, Tesslina, in 2005. Eight years later, a second daughter, Brooke, joined the clan. Valdez, a 4,000-person oil town at the end of the Richardson Highway, provided a blissful existence. They woke up to pink sunrises surrounded by nature’s skyscrapers on Prince William Sound, with world-class adventure available in every direction. But there were also warning signs. “He was always a paranoid person,” Karen says. “I thought, Well, that’s kind of weird, but it wasn’t that bad when we were young.”

Heli-skiing could be lucrative, but it was a stressful way to make a living. There were as many as six such companies operating out of Valdez, and most costs are more or less fixed, so the best way to distinguish one’s outfit is by whisking customers to the best terrain.

Cummings had long coveted the U.S. Forest Service permit that Doug Coombs had held since the mid-nineties. After Coombs sold his company and left Valdez in 2000, the Forest Service opened up the application to other operators. H2O won the permit in 2003 and ultimately secured it through 2019. It granted exclusive access to more than 200,000 acres of unending peaks blanketed in white velvet—arguably the best heli-skiing territory in the world. With everyone else left to share smaller, less desirable chunks of state and BLM land, relations were contentious. Cummings defended the Forest Service land like he owned it. He often complained, sometimes legitimately, about poaching by his competitors. They in turn argued that he was underutilizing his permit—because he didn’t take guests into the terrain often enough—and petitioned the feds to share it, without success.

H2O netted as much as $300,000 a year, enough for Dean and Karen to live comfortably in Valdez: they bought a home, two boats, and eventually a plane. Cummings designed a course for heli-ski guides and trained many who went on to to have long careers in Alaska. He prized his impeccable safety record, built on unorthodox tactics that some of his former guides still use. “He didn’t do what they say in the book,” says Eric Layton, the first splitboarder to be certified as a ski guide by the American Mountain Guides Association. “They say to dig a pit and analyze the snowpack. Dean would just read the texture of the mountain, understand how the snow came in, how it cooled then warmed or warmed then cooled. He was like the European guides in that sense. He just really understood the mountains in a different way.”

Still, Cummings had a reputation for micromanaging his guides, who tired of his authoritarian ways and frequently quit or were fired. Many called their twice-daily planning sessions “guide beatings” instead of “guide meetings.”

The least known side of Cummings was that of a doting family man. “He could be so intense and hard-driving,” Karen says, “but he just had this whole side of him that was a blast—and hilarious. He laid in bed with his kids every night and told fantastical stories. He was always loving on them, playing with them, or teaching them something.”

When each child was old enough—usually two or three—Cummings took them heli-skiing. He balanced their boots on the tips of his skis and floated through the powder as they giggled in his arms. He coached Little League and wrestled with Wyatt, attended father-daughter dances with Tesslina, and competed in family dance-offs in their living room. It was markedly different from the person his rivals saw, but that was OK by Cummings. “He didn’t have normal friends,” Karen says. “He wanted it to be just our family. And he wanted to shut all the curtains and lock the doors and never be social.”

Beneath Cummings’s chiseled, often antagonistic veneer, insecurity lurked. According to Karen, his dyslexia and struggles in school wounded his psyche for decades. Cummings didn’t learn to read until long after his peers. One night he and Karen were talking in their bedroom when he confided in her. “I pressed about why he was certain ways,” she says. “I remember him telling me that he overheard teachers in the hallway. He was walking behind them, and they were making fun of him. And it just broke his heart, hurt his feelings so badly. He said sometimes he felt so backed into a corner, he wanted to fight everything.”

Cummings broke down and sobbed in his wife’s arms. I’m so sorry, she said. You’re so brilliant. Your brain just works differently.

Cummings’s frequent marijuana use worried Karen, but it was “just weed,” he said, and it helped him focus. “I didn’t know any better,” she says. “I didn’t know I was dealing with a time bomb.” Repeated head trauma mounted, too. Cummings skied off 70-foot cliffs into his fifties, and he rarely wore a helmet. “I assume he had a series of concussions, because he would talk about it,” says former H2O guide Kyle Bates. “Getting his bell rung in competitions, backslapping and hitting his head on big cliff drops, kind of a whiplash thing.”

“I remember him in the woods, punching trees before his runs,” says Brian O’Neill, a longtime friend in Telluride and former H2O guide. “A lot of people have the physical capabilities, but the difference between Deano and everyone else was his willpower. And it showed up in every fucking turn.”

Though Cummings moved on from his street-fighting ways in adulthood, he never lacked enemies. He butted heads most aggressively with other alphas (the Alaskan heli-ski industry has plenty of those), who butted back. He frequently told other operators that they were “riding my coattails” and made a habit of reminding everyone that H2O was the only company allowed to ski the Forest Service terrain.

Cummings had a long-standing feud with Points North Heli-Adventures owner Kevin Quinn, a former professional hockey player who skied with H2O as a client before starting his own company in Cordova. Cummings also battled Josh Swierk, who bought a neighboring piece of land from the Cummingses and proceeded to launch a competing heli-ski company, Black Ops Valdez, in 2013. Swierk and his wife, Tabatha, who worked for H2O in 2004 when they moved to town, say they called the police on Cummings more than 100 times, mostly for noise-ordinance violations. 

In 2015, worn thin by her husband’s behavior and disorganization, Karen resigned as H2O’s CEO and got a job at a local phone company. Around the same time, the City of Valdez purchased ballistic shields and installed panic buttons throughout its facilities. According to a city spokesperson, the measures were not in direct response to a particular person’s actions, but one member of the community-development staff remembers that Cummings was discussed as they were taught how to implement the plan. “Literally, when I got trained, someone said, ‘If Dean comes in and starts threatening you’—Dean’s name definitely got used—‘grab this shield to protect yourself,’” says Selah Bauer, who worked for the city in 2016. “With the panic buttons, you’d push them and the police would be there. You didn’t have to call.”

Bauer and another employee requested a meeting with police chief Bart Hinkle, and they discussed Cummings at length. Cummings’s behavior—and the police department’s inability to stop it—still rankles Bauer. “Alaska has kind of a live-and-let-live motto,” she says. “But it also seemed like their hands were tied.” 

In April 2020, Hinkle agreed to answer questions via email for this story, then never responded. A spokesperson later said the police chief “will be unable to participate in an interview about Mr. Cummings.”

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