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The 9 Faces of Dean Cummings

Evolving from rough beginnings into a skiing legend, Dean Cummings is no simple character.

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Editor’s Note: On. Feb. 29, 2020, former professional big mountain skier and legendary Alaska heli-ski guide Dean Cummings, 54, was arrested and charged with the second-degree murder of Guillermo Arriola. On Nov. 10, 2022, Cummings was found not guilty of the charge. The following is a profile of Cummings originally written by Tracy Ross and published by Skiing Magazine in 2006. 

Dean Cummings: Punk-Ass Kid

Dean “Rock Jaw” Cummings grew up pillaging the streets of Los Alamos, N.M., with Spanish Indians and bored, angry white kids whose lab-coat-wearing grandfathers helped develop the Bomb. The kids were tough; but tiny, freckled Dean was tougher. “Dean was a whirlwind,” says his mother, Carol, laughing at the thought of her wild-eyed fourth child. “He was small, but he was scrappy. You didn’t pick a fight with him-and if you did, you were dead.”

Punk-ass Dean couldn’t stand his teachers telling him what to do and who to be. Almost daily, he’d skip town, head to the high desert between Los Alamos and Santa Fe, build fires, and throw hatchets in the dirt. He’d space out, thinking about what the grown-ups had said. He’d sit for a while, then get up, start sprinting, and leap off a 50-foot sandstone mantel, landing—poof—in the silky red dirt that felt just like the powder snow he would become addicted to later in life.

By the time he hit puberty, Dean was into booze, Zeppelin, skipping school to ski at Pajarito Mountain, and stealing his parents’ car. His sentence: a two-week hoods-in-the-woods program with Santa Fe Mountain Center in Colorado’s Collegiate range, including a self-esteem-building overnight solo at the end. Dean aced the course. Then he pulled a fast one on his counselors. “He had a little can of waterproofing and a safety pin or something,” says Carol. “He just took off fishing and camping. They couldn’t even find him. Dean’s always been… resourceful.” Impressed, SFMC hired him on as a guide.

Still, at 17, he got busted doing 160 mph on a custom super-bike down the centerline through town and stood in front of his parole officer for the fourth time in two years. The one place where he could avoid trouble? In the mountains.

Dean Cummings: Legendary Guide

Former extreme skiing world champion and heli guide Dean Cummings stands in downtown Valdez with the 5,000-foot
Former extreme skiing world champion and heli guide Dean Cummings stands in downtown Valdez with the 5,000-foot “Mile High” mountain looming above his right shoulder. 

Well, he’s a legend to the few thousand surgeons, investment bankers, and piggy-bank-smashing ski bums who shell out thousands of dollars to book heli-ski trips with Dean Cummings’s H2O Guides, which flies clients into 1.6 million acres of Chugach Range.

Since 1994, when Dean started H20 out of the back of a 1970s Dodge van called the Love Machine, he has coaxed heli pilots onto 4,000 landing zones, most of which he dug out with his own ham-hock-shaped arms. At 5 feet, 11 inches and 185 pounds, Dean isn’t stocky so much as dense. His chest looks like a pony keg, and his legs fire like a couple of Mack truck pistons.

“I’ve seen Dean shovel for an hour and a half straight,” says David Learned, a financial heavy from Boston who hires Cummings and a private chopper (at $3,650 dollars an hour, 20 hours minimum over 10 days) every winter. “When you get up there, the crest on either side is six feet high and the pad is eight feet wide. You can’t stop him.”

Dean has dropped 6,000 descents in Alaska. His company, the longest-running of its kind in Valdez, has the largest permit area of any heli operation in the world. Perhaps most important, H2O has the best safety record in the heli-ski industry. “The worst injury anyone’s ever had in my care is a blown knee,” he says.

Dean Cummings: Hardass

It’s a blisteringly sunny spring day in the Chugach, and Dean steps out of a Bell 407 and raises a ski pole. “You’re about to access the goods!” he says emphatically.

My group—Santa Monica real estate developer Mark Kelton, two young guys from Colorado, and I—look up from where we’re standing ankle-deep in melted snow. Massive wet slides pour down 5,000-foot faces. Two days ago, it dumped five feet—and then the mercury climbed to 58 degrees and turned everything to mush. With instability on most aspects, all we can do is ski low-angle, knee-tweaking slop—over and over again.

Kelton is coming off a two-day high of ripping down porcelain-blue flutes, hemorrhaging bliss all the way. But it’s not enough. Having forked over three grand for the week, he wants his money’s worth. He dips and weaves away from the group, teasing his tips toward a potentially loaded face. Every time, Dean reels him back in, until finally Kelton pushes too far.

“So, Dean,” he says for the third time in an hour, “when we gonna ski something steep?”

Dean drops his poles to his sides, his jaw muscles drumming along the bone. “I told you, we’re not going to. You can pay to fly out if you want to,” he says, and skis off.

No, you don’t. Not if they’re disobeying on the hill. Not if they’re not paying attention at all times. Not even when it means telling a pro skier, in the Chugach to film next year’s big movie, that you won’t pluck her off a ridge when she’s too scared to drop in. Never let somebody guide you. Remember that. His critics remember, and then resort to clichés like “bull in a china shop,” “loose cannon,” or, simply, “egomaniac.”

“Dean has a…super-independent personality,” says Joe Royer, president of the Heli Ski U.S. Association, a group of nine heli operators that promotes the sport and lobbies for safety and education. “Sometimes that helps him, sometimes it hurts him, and sometimes there’s just too much of Dean.”

“This business has made me hard in a lot of ways,” says Dean. “I’ve seen so much shit go down. That’s why I’m so hard-driving. Other operators can make mistakes. No one can be better than us. I want to raise the standards, protect the industry, and provide the highest-quality experience I can.”

Dean Cummings: Champion of Children

In 2005, Dean founded Be Snow Smart, a winter-skills program for kids that was endorsed by Alaska governor Frank Murkowski, who declared December Avalanche Awareness Month. In 2006, Cummings traveled around the state, telling his life story and giving kids basic avalanche education, then he expanded the program to include Be Wilderness Smart and Be Water Smart.

“I want kids to realize that even if they don’t relate to school, there’s a whole other world out there,” says Dean, who’s married with two kids of his own. “They can be a heli pilot, a mountain manager, ski patrol-and it’s totally legitimate. This is education for a reason.”

Dean Cummings: Smooth Operator

Dean Cummings on Woodworth Glacier in the Chugachs of Alaska
Dean Cummings on Woodworth Glacier in the Chugach of Alaska.Photo credit: Josh Cooley

One of Dean’s first jobs out of high school was on a seismic-geology crew. He was nimble and, having rock climbed, he knew knots. So when the bosses asked him to dangle under a Bell 206 helicopter or ski into remote locations and place explosives, he gladly obliged.

Though he doesn’t have a pilot’s license, Dean can fly a helicopter, land a helicopter, and guide fear-crazed pilots out of what looks like certain death. Like that time in Iran with the Russian Mil 28 transport chopper full of pro skiers that was about to crash into the Alborz Mountains. “I looked out the window and saw the rotor about to hit rock,” recalls Warren Miller film star Chris Anthony. “I thought we were going to die. But Dean’s up in the front, yelling at everyone to get ready to jump.” They didn’t have to. Dean talked the pilot down to safety.

Under more normal circumstances, he’s likely to hop out of a hovering bird, attach himself to the side of a mountain with an ice ax, and ski a line so steep you could look between your ski tips and see tankers sucking oil out of the pipeline on Prince William Sound.

Watch: Warren Miller Iran Segment with Dean Cummings

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Dean Cummings: Control Freak

“This is going to be super-positive, right?” It’s October, and Dean has called me at the office. He hears I’ve been poking around, asking people questions. “You promised I was going to be stoked,” he insists.

By November, Dean will have called my boss, my boss’s boss, and the managing editor of our website. He wants to be sure that I’m not raking him over the coals.

As the sole proprietor of H20 guides, Dean is an all-around operations guy. He does ground ops, office ops, weather ops, and mountaintop barbeque ops. He takes film crews into the steepest terrain and then one-ups their star athletes with 60-foot airs and first descents. He insists on doing his own PR, touring mountain towns each fall with a low-budget DVD. He even dashes off his own press releases, which he always signs “Skiing is Life!”

In 2000, while filming with Matchstick Productions, Dean misjudged his line by three feet, aired an 80-foot cliff, and landed on a flat spot. The damage? Two broken ribs, a fractured sacrum, and a shattered tibia/fibula. After two weeks in the hospital, he kept tabs on his crew via two-way radio from his couch in Valdez, informing them of conditions on aspects that were miles away.

“It’s not that Dean won’t listen to your ideas or put your concerns into play,” says Spencer Wheatley. “His relentless intensity and persistence sometimes blind him. He’ll keep ramming his head against the wall without noticing that he could just walk around it.”

Dean Cummings: Avy-Control Freak

Dean rises at 4 A.M. and starts scanning the mountains for wind loading and new slides. By 5:30, he’s scoured the weather forecast-created by snow-safety director Peter Carter using two satellites, the National Weather Service, the National Oceanic and Atmospheric Administration, the Alaska Department of Transportation, and four local weather stations. Then he and his lead guide decide on an area of operation. By seven he’s in the bird, motoring past mountains like Meteorite, The Books, and The Tusk.

At 7:30, he jumps out of the heli into waist-deep snow and digs a pit. He does compression tests and shovel shear tests, then digs hasty pits for the next 5,000 vertical feet. He ski-cuts double fall lines, and tests for instabilities that could slide if triggered by a skier. By the time he’s through, he knows which spots have microclimates that will hold snow and which ones are likely to avalanche.

To date, Cummings has never fully buried a client. There are conflicting reports about film skiers getting partially buried-skiing lines that clients would never get near. And a guide got buried once, in 1999, on a day known as “Black Monday” when several clients from other operations were buried in slides. It was a rare occasion when Cummings relinquished control, handing the reins to one of his guides. “When it comes to snow,” says Brian O’Neill, a friend and former guide, “Dean Cummings is right 999 out of 1,000 times.”

One day in April, while he and I were dropping powdery flutes without incident, every other heli operator in Valdez buried at least one client.

Dean Cummings: Badass Skiing Mofo

Dean Cummings skis the Holy Grail in the Chugach Mountains of Alaska
Descending the Holy Grail in the Chugach Mountains of Alaska.Photo credit: Dean Cummings

It’s 1991, and Dean Xeroxes an entry form for the inaugural World Extreme Skiing Competition in Valdez, Alaska. He’s managed to parlay his tough-kid Pajarito Mountain days into a winning career as a mogul skier on the U.S. Team, with several podium finishes. Now he’s preparing to pit himself against some of the best skiers around. In the contest, Dean flashes his line, a 50-degree face with a 60-foot air down the middle-and takes second place to a rippin’ Jackson Hole skier named Doug Coombs.

Today, Dean is one of the best big-mountain skiers in the world-the best, some would argue. His style is a combination of Humvee power, catlike balance, and no-fear aggressiveness. He has the fast-twitch agility of a mogul skier and the clean, balanced turn of a GS racer. And he almost always stomps his landings.

“Nothing beats drag racing in the mountains with Dean Cummings,” says Brian O’Neill. “Yeah, he’ll have you ski something that may make you wet your pants in one second, but at the bottom you’re hugging him.”

Dean Cummings: Icon

You can listen to the sniping stories and read the profiles, but you’ll never get a glimpse of the real Dean Cummings until you go to Alaska and follow him down the snow-caked mountains he claims as his backyard. The first time you see him drop his tips down a 50-degree face and let his freakish athletic instinct take over, you’ll understand why he’s widely admired and occasionally loathed. That’s what it takes to be a captain of industry, a leader, and maybe the best guide in Alaska.

You’ll follow Dean down shaded blue couloirs and feel as safe as you would on your living-room sofa. You’ll get greedy and be scolded. You’ll watch him charge a face with two inches of crust and finesse it like it was boot-deep fluff. Maybe you’ll see a hotheaded cowboy from New Mexico. Maybe you’ll see a charitable, even-keeled entrepreneur with the greatest job on earth. But you’ll sure as hell see that he can ski and guide like nobody’s business, and that he knows the Chugach better than anyone in the world. You’ll leave Alaska knowing nine different guys—all of them named Dean Cummings.