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A pilot’s love for the mountains built a house on Denali. Now it’s at the center of a family dispute.

  • Author: Zaz Hollander
  • Updated: February 19
  • Published February 16

Pioneering glacier pilot Don Sheldon and his wife, Roberta, left a hand-built legacy a mile up North America's tallest peak.

A six-sided cabin perched at 6,000 feet on a rock nunatak at the top of Ruth Glacier, the Don Sheldon Mountain House became a landmark for Denali flightseers in the yawning ice-scoured bowl known as the Don Sheldon Amphitheater.

Now the hut in the granite heart of Denali National Park and Preserve is part of a bitter legal battle that's exposed a deep schism between the Sheldons' adult children.

Daughter Holly Sheldon Lee, a pilot who owns an air service with her husband and lives in Talkeetna, sued her brother Robert in 2015 over his administration of the $1.7 million family trust and her access to the house. She appealed to the Alaska Supreme Court after lower-court judges sided with Robert.

Son Robert, an international businessman with a home in Anchorage, says he is carrying out his mother's wishes as required and his sister is refusing to comply with a settlement she signed more than two years ago that gave her a third of the trust, including the mountain house.

A third sibling, Kate, lives in the Lower 48 and is aligned with her brother in the dispute but not named in the suit.

Robert, Kate and Holly Sheldon spent Valentine's Day in front of the state's highest court.


Hours before the Supreme Court hearing started Wednesday, Holly Sheldon posted a Valentine's Day greeting on Facebook to her brother and sister that ended, "…just need to get a couple things straightened out."

The day after, her tone changed: "The intense battle from money and power at any cost will knock your socks off if you aren't cognizant & careful."

Holly Sheldon at the Alaska Supreme Court on Wednesday. (Bob Hallinen / ADN)

The family dispute centers on the trust left by Roberta Sheldon when she died in 2014. Don Sheldon died in 1975.

Don Sheldon, who built the mountain house on Denali's south face with friends in 1966, is known as perhaps the most famous pilot to fly on the mountain. He operated Talkeetna Air Service.

Roberta, born into aviation as the daughter of glacier pilot Bob Reeve, became a fixture in Talkeetna community matters and activism and wrote books on local history.

Roberta designated her son to oversee the trust.

Holly sued her brother in 2015 over claims she didn't get complete information about trust assets from her brother, according to a brief filed in the Supreme Court case.

She also contended a December 2015 mediated settlement wasn't valid because she was feeling sick during the 9-hour negotiations and didn't realize the paperwork she signed was the actual settlement.

The settlement included a $25,000 payment for legal costs to Robert and gave Holly a one-third share of the Mountain House LLC and the right to visit the cabin provided it didn't interfere with the business.

Robert Sheldon at the Alaska Supreme Court on Wednesday. (Bob Hallinen / ADN)

A Superior Court judge found in Robert's favor in 2016. Holly was ordered to pay Robert legal costs.

"While the court rulings have clearly upheld my actions each step of the way, Holly has sadly chosen to use social media and others to advance inaccurate statements that are degrading to the tremendous legacy of Don and Roberta Sheldon," Robert Sheldon wrote in an email. "As Trustee I chose to provide Holly with an interest in the Mountain House LLC."

His sister got a share in the Mountain House LLC but not a voting interest, Robert's attorney said in an interview.

"Because Holly had created so many problems already," attorney Kevin Clarkson said.

Hut to chalet

The nearly 5-acre Sheldon property sits on an inholding within the Denali National Park, according to Tucker Chenoweth, a National Park Service ranger who works at the Talkeetna visitor center.

Sheldon Chalet. (Sheldon Chalet)

A new 1,000-square-foot hotel — the 5-room Sheldon Chalet — just opened for guests on the same property as the mountain house. The 212-square-foot hut is still open for day trips or overnight stays.

The court case has nothing to do with the chalet, Robert Sheldon said. Holly said she didn't want to say too much about the chalet because of the ongoing proceedings.

"But I do want to say, maybe my brother advertises it as a Sheldon family business and it's not true," she said.

The chalet is a rarity in Alaska: luxurious accommodations in such a remote locale.

The chalet was part of his parents' plans all along, Robert said.

"Three generations of the Sheldon family have worked to make the vision of Don and Roberta Sheldon a reality," the chalet website says. "The Sheldon Chalet welcomes visitors to experience the wildness of Alaska in comfortable luxury, just as the elder Sheldons intended."

Inside the Commons at Sheldon Chalet. (Sheldon Chalet)

Flying rights

The lucrative air taxi business to the Sheldon property is also part of the dispute.

Back in 2014, after their mother died, Robert promised Sheldon Air Service the exclusive right to ferry visitors to the mountain house, Holly said in an interview Thursday. But by early 2015, she contends, he awarded the contract to a competitor.

"It was between a quarter and a third of our business," she said, of the mountain house taxi trips. "This is a story about power and money. It's a story about the remainder of our Sheldon family relations and how my mom's wishes have been carried out after her death."

Sheldon's original lawsuit referenced the claim that her brother deprived her of the contract.

Robert, asked about the contract, replied by email: "Holly never had an exclusive right for anything to do with the Mountain House LLC, yet demanded one. Immediately after Roberta Sheldon's passing Holly obtained aggressive legal counsel and began pressuring me as Trustee with various demands inconsistent with the Trust that I am beholden to uphold."

The future of that trust is in the hands of the state's highest court now.

Valentine's argument

Arguing before all five Supreme Court justices Wednesday afternoon, Holly Sheldon's attorney asked that the settlement be set aside.

His client got physically ill during the 9-hour mediation session in 2015 and thought she was signing only a proposal, Fairbanks attorney Robert John said. He also argued the settlement did not rise to the level of binding arbitration.

John urged the justices to develop a new "bright line" ruling requiring a trustee like Robert who is also a beneficiary to "disclose all information prior to settlement" and assigning all risk and responsibility to them.

John said Holly never got $30,000 worth of jewelry and $27,000 in paintings and family heirlooms.

"Has Robert sold those to finance some kind of venture? We don't know the answers to that," he said.

Robert Sheldon's attorney told the panel that the case centered on Holly Sheldon's refusal to follow a settlement agreement she entered voluntarily.

The Sheldon Mountain House in 2010. (NPS photo)

The agreement she signed included statements like "agreement to a settlement of all claims of all parties" and "as a result of the full and complete settlement reached today," attorney Matthew Clarkson said. "No reasonable person could think that's not a settlement."

He also said Holly Sheldon had enough information about the financial status of the trust to decide whether to sign the settlement.

Several justices asked questions centering on the settlement and whether it rose to the level of arbitration.

A decision could take at least six months.

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