SAM Magazine—Big Sky, Mont., Feb. 23, 2026—Taylor Middleton, the longtime Big Sky Resort executive who led the Montana destination through decades of expansion and repositioned it as one of North America’s premier ski resorts, died Friday at his home in Big Sky. He was 68.

An Alabama native and 1979 University of Alabama graduate, Middleton arrived at Big Sky 46 years ago as a front desk attendant at the Huntley Lodge. He moved into sales and marketing, became general manager in 1998, and later served as president and chief operating officer. He stepped out of day-to-day leadership in October 2024 and continued as an advisor.

“Taylor Middleton was one of the most impactful leaders in the history of the American ski industry,” said Boyne Resorts CEO and president Stephen Kircher.

Over nearly three decades in top leadership roles, Middleton oversaw the construction of more than 20 lifts, two trams, two slopeside hotels, and major summer infrastructure that helped reposition Big Sky as a year-round destination. He also led the resort through the 2008 financial crisis and oversaw the integration of Moonlight Basin and Spanish Peaks.

In 1998, Middleton embraced what Kircher described as a “Big Hairy Audacious Goal” to make Big Sky the number one resort in North America. Last year, the resort topped SKI magazine’s annual reader survey rankings. “There is no one more responsible for that accomplishment than him,” Kircher said.

Under Middleton’s leadership, Big Sky completed its Vision 25 capital plan, including a new Lone Peak Tram and two-stage, out-of-base gondola. Middleton also played a central role in Boyne Resorts’ Forever Project, the company’s 2030 net-zero initiative.

Middleton’s influence extended well beyond Big Sky. Over the course of his career, he mentored leaders across Boyne’s 13-resort portfolio and the broader ski industry.

Nick Herrin, who began his career as a ski instructor at Big Sky and now oversees snowsports across Boyne’s resorts nationwide, said, “My career was shaped by the goals he set for me.”

“Big Sky would not be what it is without Taylor Middleton. His fingerprints are on everything good about this place—and they always will be,” said Middleton's successor, resort president and COO Troy Nedved. 

“Some of my best adventures were with Taylor,” said Big Sky vice president of mountain sports Christine Baker. “It was never about keeping up or proving yourself. He had a rare way of making people feel at ease and making it about the experience, the people you were with, and truly enjoying this place.”

Beyond the resort, Middleton was deeply involved in the development of the Big Sky community. He played key roles in the formation of the Resort Tax District, Chamber of Commerce, Transportation District, and the establishment of the community’s first hospital and bank, serving on inaugural boards and advocating for long-term civic infrastructure.

"He fought tirelessly for things that had nothing to do with skiing: a hospital so our neighbors wouldn't have to drive hours in an emergency, a high school so our kids could grow up and stay rooted here. He always put people first," said Nedved.

An avid skier and mountain biker, Middleton was known for logging 100 days of skiing annually and for regularly holding on-snow meetings. He remained active in Big Sky’s mountain culture, competing in local races including The Rut and The Biggie through 2025.

Middleton is survived by his wife, Barbara Rowley, and daughters Anna and Kate.