Jesse Dempsey, a longtime local resident described by friends as having “phenomenal athletic ability,” died unexpectedly Saturday. He was 42.
Dempsey, a 1995 graduate of Aspen High School, is said to have been an integral part of the local youth movement that raised the popularity of snowboarding back when it was taboo on local ski runs. In the early days of snowboarding and amateur competitions, he was more interested in doing things in a unique way rather than satisfying judges, according to friends.
“He was so good the judges wouldn’t know what foot he had forward, they couldn’t tell what his dominant direction was,” said Matt Isaac, a freshman when Dempsey was a senior.
Michael Nakagawa met Dempsey in the sixth grade after Dempsey’s family moved to Aspen Village. They grew up together, and Nakagawa recalls Dempsey making the transition from “rough-and-tumble kid who fought all the time” to an “amazing snowboarder” who got sponsorships in high school from snowboard companies. This was at a time when snowboarding was not widely accepted.
“He was the first kid doing ‘switch 700s’ and ‘switch 900s,’” Nakagawa said. “He was one of the first Aspen snowboarders to take it to the next level.”
As of Monday afternoon, the cause of death was unknown. Autopsy results won’t be available for three weeks, said deputy coroner Eric Hansen of the Pitkin County Coroner’s Office.
Isaac said he ran into Dempsey on Saturday morning at the city’s Arbor Day tree giveaway in Paepcke Park.
“He looked good, he said he was working a lot, and he was tired,” Isaac said.
He said on Saturday, Dempsey related a story from several years ago, when he was working on the mountain as a snowmaker for Aspen Skiing Co. The story exemplified how loyal Dempsey was to his friends and coworkers.
There was some drinking on the hill one night — snowmakers have been known to imbibe alcoholic beverages when temperatures are well below freezing; some say it helps them to keep warm — and one of Dempsey’s co-workers tipped over a snowmobile and lost a two-way radio.
“The next day, when Jesse went to work, they were talking about it, and he said, ‘I know where he fell, I can find the radio.’ He went up the mountain and found the radio. He came back down, and [company managers] asked if he had been drinking the night before. He said it was the only night of the ski season that he drank, and he didn’t want to lie to them.
“He told them he had been drinking and didn’t say anyone else had been drinking. They told him he was a great guy, but they couldn’t let him keep working,” Isaac said. “He was fired because he was the only one who had been honest about what happened the night before.”
While some of Dempsey’s friends mentioned that he faced substance-abuse issues several years ago, they were quick to add that he got his life on track after he married and became a father. He also spent time in recent years coaching snowboarding and skateboarding to local youths.
Julie Wyckoff of Old Snowmass said Dempsey was a friend of her children as he was growing up, and spent a lot of time at the Wyckoff home before graduating from high school.
“He’s the most athletic human being I have ever seen,” Wyckoff said. “He would fly through the air like a hawk or an eagle.”
Dempsey took up snowboarding when it wasn’t allowed on official ski areas, back in the days when skiers looked down on the sport. “There was no high-school letter you could get for snowboarding then,” Wyckoff said.
Even on a trampoline, Dempsey would amaze onlookers by bouncing so high, he could see what was going on through the window of a two-story house, she said.
“We considered him part of the family,” Wyckoff said. “He was very much an inspiration to me.”
She described Dempsey as “a kind teacher, a deep thinker and a pretty good artist. He was just good at anything he did.”
But he also had an “unconventional approach” to life, and could be a very private individual.
“He was his own man,” Wyckoff said. Rather than seeking attention, “he was more interested in being out on the mountain and getting big air when no one was watching him.”
Dempsey was one of the “cool kids,” often mentoring and teaching those who were a few years younger, but he was “a real person,” she added.
“He didn’t have the slightest idea that he was cool,” Wyckoff said.
While Dempsey faced some challenges as an adult, he worked hard to overcome them, she added. “He was a great father and a wonderful husband,” Wyckoff said.
Friends said Dempsey held a variety of jobs over the years, from valet parking to restaurant work — doing whatever he could to support his family and continue his passion for snowboarding. Most recently, Dempsey had become a certified technician in the business of recovering Freon from air-conditioning units and other appliances and ensuring proper disposal of the commonly used refrigerant.
Brian Wexler, owner of Sidewinder Sports in Snowmass Village and Valley Valet Parking and Party Services of Carbondale, said he employed Dempsey for a few years. He was personable, dependable and hard-working, Wexler said.
“I haven’t had a lot of contact with him recently,” he said. “I knew him better several years ago when we were all working and doing valet together. When he was younger, he hung out at Sidewinder quite a bit. He was an employee and a friend.”
Social media was filled with the news of Dempsey’s passing on Sunday and Monday. Nakagawa’s tribute garnered a lot of response.
“Completely gutted to hear about our friend, and local, Jesse Dempsey’s sudden death,” Nakagawa wrote. “I’ll always remember meeting Jesse in sixth grade, with his long, Axl Rose hair and rough attitude. He later became one of the most natural snowboarders most of us ever got to ride with, and he made it look so effortless.”
The post continued, “Every time we lose another friend, it’s like a piece of our youth goes with them, but we’ll always have their indelible memories and legacy going forward. … Ride in peace, old friend.”
A formal obituary was not available by press time Monday. Isaac said he planned to organize a snowboard outing this weekend at the summit of Independence Pass to bring Dempsey’s friends together.