Legendary longtime Aspen local John Callahan, who led a life of adventure, dies at 95

John E. Callahan lived in Aspen and worked as a ski instructor, patrol and trail crew worker at Buttermilk. He died Jan. 1 at the age of 95.

Courtesy of the Callahan family

John E. Callahan, a longtime ski instructor, Mountain Rescue pioneer, and active community member, died at the age of 95 on Sunday.

“We’re all lucky. All four of us were there and held his hand as he passed away,” said Pat Callahan, 57, his son. His siblings John Callahan, Anne Marie McPhee, and Nancy Humphreys were with him. 

Callahan and his late wife, Cynthia, were inducted into the Aspen Hall of Fame in 2017.

John and Cynthia Callahan in Wagner Park, circa 1965.

Courtesy of the Callahan family

The couple met on a ski vacation in Sun Valley, Idaho, in 1959. As the story goes, he asked her to marry him the night they met. They married soon enough in 1960 and moved to Aspen from Los Angeles in 1965, seeking a smaller town to raise their growing family. 

Callahan worked briefly in hospitality at the Applejack Inn and bartended at the original Little Nell. Then, he turned to the slopes to work as a ski instructor, patroller, and on the trail crew at Buttermilk. 

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One of the first ski instructors fluent in Spanish, Callahan encouraged Aspen Skiing Co. to recruit skiers from Mexico. His love for Latin America and speaking Spanish endeared him to many Spanish-speakers in the valley and became somewhat of a running joke in his family. 

“He was a legendarily bad shopper because he had to speak Spanish with every single person at City Market. And, it would take him two hours to get in and out of the grocery store,” Pat recalled about his dad.

Callahan’s daughter Nancy, 51, remembered a time that his enthusiasm for conversing in Spanish with native speakers resulted in gifts at the grocery store.

“He went to City Market and came out with religious candles because the ladies at the register liked him so much, they were sticking things in his bag,” she said. “When he talked to you, you were the most important person in the world — which I think is what drew a lot of people to him.”

Callahan was born in Boston on Sept. 21, 1927, and moved with his family to New York City when he was 8. 

In 1945, at 17, he enlisted in the U.S. Army and attended jump school to become a paratrooper with the 82nd Airborne at the end of World War II. In 1950, he won the New York City Golden Gloves Amateur Light Heavyweight Boxing Championship. He graduated with a business degree from New York University. 

Callahan sailed to Bermuda in the early 1950s. Courtesy of the Callahan family.
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Callahan craved an adventurous life. He hopped rail cars, bicycled, and rode his motorcycle through Mexico, as well as crewed on a schooner in the Atlantic Ocean.

He passed that adventurous spirit and appreciation for the outdoors to his kids. After yanking them out of school, Callahan took the kids on mega-adventures that provided a different brand of education than the school curriculum.

“When I was 13 and my brother was 15, (our dad) said, ‘Let’s go ride our bikes down Baja California through Tijuana.’ We slept on the side of the road, and my mom must have thought he was nuts, but he’d take us out there and do things like that,” Pat said.

And, Callahan and Cynthia would let the kids camp by themselves. Pat and Nancy remembered their parents would help them pack up their gear, load it up in their old red Jeep, and drive up to places like Chapman Reservoir and leave the kids in the wilderness for the weekend.

“I know in this day and age — because I coach kids — no parents could get away with that!” Pat said. But, they both regard those memories as some of the best of childhood.

The Callahan family in 1971. Cynthia, holding Nancy. John, holding Anne Marie. Pat and John Jr. in front of them.
Courtesy photo

A love for the outdoors also comes with a healthy dose of danger. 

Callahan was one of the first members of Mountain Rescue and was likely one of the first people to be dropped off at the Maroon Bells from a helicopter.

He worked with the organization for over 25 years and assisted with hundreds of rescues. The stories from rescues, some grisly and some comical, instilled a respect and reverence for the dangers of nature for Callahan that he shared with his kids.

Avalanches, rock climbing accidents, and drownings all happen in the mountains. 

“I remember when I was a kid, the phone would ring at 2 o’clock in the morning, and my heart would sink because I knew that he was going to go out there in the mountains in the dark with the other guys, and he would just completely risk his life,” Nancy said. But, he always came back … though sometimes not for a few days.

Pat said because his dad was among Mountain Rescue’s first members, the team frequently did not have adequate gear or was ill-prepared on rescues. 

“One night, they got to a dead body. But, they didn’t have their camping gear, and the helicopter couldn’t get back up to retrieve them,” he said. “And, Dad said he was about to die of hypothermia. And finally, he looks at the dead body and goes, ‘Why does the dead body get the body bag?’ So, he took the body out, and he crawled in to stay warm for the night.”

Callahan was a lifelong runner and founded the first town running race, which evolved into the Golden Leaf half-marathon. 

He retired from the Skico in the ’90s, and, in his retirement, he served as a greeter at the Aspen Valley Hospital. He also was one of the founding members of Aspen Savings and Loan Association.

Cynthia died in 2005. They were inducted into the Aspen Hall of Fame in 2017 and Aspen Valley Ski & Snowboard Club Hall of Fame in 2018.

John was preceded in death by his wife, Cynthia, his grandson Hunter, and his siblings Ambrose, Estelle, and Jean.

He is survived by his younger brother, Bobby; his four children John and Patrick Callahan, Anne Marie McPhee, and Nancy Humphreys; his grandchildren Tiffany, Kelli, Keegan, and Kevin Callahan, Nell, and Teddy Humphreys, and Kenny and Molly McPhee; and his daughter- and sons-in-law Kathleen Callahan, Billy Humphreys, and Jim McPhee.

When the Callahans first came to Aspen to consider moving, they asked a local what they should go see. The local replied, “Oh, you should go see the Bells! But, you can’t go up in that station wagon.” And, he tossed her parents the keys to his Jeep, Nancy said. 

The local told the couple to use his Jeep to drive up to Maroon Bells and leave it parked near his house with the keys inside the next morning. That’s when her parents knew that Aspen would be home, she said.

“I think Aspen gets the image of being very glitzy and glamorous. But, underneath there’s still a very strong fabric of the families that just grew up together. And, there’s always room for new families to join the equation,” she said.

Locals like Callahan helped define the much-discussed “Aspen character” — nature lovers deeply engaged in the community who tossed their kids out into the wilderness. 

Across the decades in which he and his family lived in the Roaring Fork Valley (Pat now lives in Basalt, and Nancy lives in Maryland), the family witnessed their home morph from a small ski town tucked in the Rockies to a world-class ski resort that attracts the international 1%, along with ski bums looking for a bartending gig to fund their mountain escapades. 

His kids hope to see his legacy carry on in the coming generations of locals and transplants to their hometown. 

“He would do these things just for the love of the community and almost like a responsibility to the community to give back,” Pat said. “And, I think that’s what Aspen has thrived on through these years, you know, not just him. But, other people have taken that approach, too.”

Details for a memorial will be announced at a later date.

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