Jack Oleson, an initial Vail Mountain investor, turns 97 Friday

Eagle County rancher and entrepreneur remains mobile and sharp

Jack Oleson in April. The original Vail investor turns 97 on Friday.
John LaConte/Vail Daily

As legend has it, Vail Mountain started with six general partners and a few dozen investors who paid $5,000 apiece to be a part of the company.

Those investors received a piece of land for a home site in Vail Village and four lifetime ski passes, says Jack Oleson.

Today, the lifetime portion of that commitment to those initial $5,000 investors has expired for everyone but him, Oleson said. Oleson turns 97 on Friday.

“I think I’m the only one left,” he said of Vail’s original investors.

Oleson’s daughter, Charlynn, got a lot of use out of her lifetime pass, and still does to this day. But Oleson didn’t use much of his unlimited ski access, he said.

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“I never did ski,” he said. “I did half a day and thought ‘I don’t need a broken leg, I got work to do.'”

Oleson instead preferred to break his legs while pursuing his primary passion of ranching.

“I broke them both on horseback, at different times,” he said.

Ranching and recreation

Oleson was born and raised in a ranch house about a mile east of Gypsum.

“It was between the railroad tracks and the river,” he said of the area at the time.

He married Charlotte Nottingham in 1948, ranched the areas that would become future recreation destinations, working the Beaver Creek valley with the Nottingham family and ranching sheep on Meadow Mountain.

Ranching would take Oleson all over the world in the ’60s and ’70s; he took part in a historic cattle shipping operation in which the government of Chile paid millions to receive Polled Hereford cattle from Oleson and others via air shipment from the U.S. Oleson also raised cattle in Taiwan.

But prior to those years, back in Eagle County, Oleson said he knew the recreation industry was coming and would change the area, bringing investment with it.

Through ranching, Oleson knew another Eagle Valley family, the Eatons, who had one family member in particular who also saw the tide of recreation coming.

Jack Oleson at his home in Eagle on April 5, 2022. Now 97, Oleson is still fully mobile and sharp.
John LaConte/Vail Daily

‘I figured it would go’

Oleson’s friend and Eagle Valley neighbor Earl Eaton had mastered skiing on pine board skis his father made at their home in the Edwards area of Eagle County where they logged and ranched.

For Eaton, skiing started as the most efficient way to exit a logging chute, but he later used the skill to become a patrolman and snowcat driver in Aspen.

Eaton loved the sport and wanted to build a ski mountain on some slopes he had discovered near the area where he grew up in Eagle County.

In the years before Vail Mountain opened in 1962, Oleson said Eaton had developed a reputation in the Eagle Valley as an expert on the area, which would today be identified as Mid-Vail, hiking up to the area and measuring snow totals for years before Vail Mountain would be discovered by skiers.

“I think Earl had more to do with figuring out the good ski runs than anybody,” Oleson said.

Eaton showed the area to 10th Mountain Division veteran and expert skier Pete Seibert in 1957, and the rest is history.

“Earl and I had shared this desire to find the perfect ski mountain since we first met in Aspen in 1947,” Seibert writes in his book “Vail: Triumph of a Dream.”

Oleson was watching the situation develop and wasn’t afraid to take a gamble.

“I figured it would go,” he said. “I remember loaning Pete Seibert (some funds) and he found an angel not too long after and bailed me out.”

A photo of a Dec. 16, 1966, article in Skiers’ Gazette, from Jack Oleson’s collection.
John LaConte/Vail Daily

Ski area owner

Oleson said after Vail started, he realized there could be more potential in skiing than in sheep ranching on his land at Meadow Mountain.

“We built a little lift line, I think it only went 900 feet in elevation,” he said.

Oleson is pleased to hear that despite the removal of that lift line, people are still skiing at Meadow Mountain today as a popular Eagle County ski touring area.

“Lots of people learned to ski there, and then they went to Vail,” he said.

One day, while visiting Tom Stone, pastor of St. Patrick’s Roman Catholic Parish in Minturn, Oleson was reminded of the difficulties of being a ski area owner.

“I was sitting in Father Stone’s house and got a call. They said something about three of the chairs falling off the lift,” Oleson said with a laugh. “But the snow was deep, and there wasn’t anybody in them, and no one got hurt.”

A photo of a page about Meadow Mountain from Jack Oleson’s scrapbook.
John LaConte/Vail Daily

Now 97

Today, Oleson lives on the Diamond S Ranch in Eagle, where he spent many years as the ranch manager and still does work around the grounds when he can.

He says throughout his life, he always tried to start his day with a good breakfast of bacon, eggs and toast.

After that, it didn’t much matter to him, he said.

“I’ve took baloney sandwiches out of my saddle bag that were four or five days, maybe a week or two weeks old, and ate them, because that’s all there was in there,” he said.

He’s still mobile and sharp, and credits his longevity to a lifetime of hard work.

“I always had a project, I was never idle,” he said. “I never did sleep much.”

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