Longtime Big Sky Resort Leader Taylor Middleton Dies at 68

Middleton spent 44 years at the resort, including 30 years in top leadership roles, and was known for his passion for the outdoors and community involvement.

Published on Feb. 21, 2026

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Oliver Taylor Middleton, who spent 44 years working at Big Sky Resort in Montana, including 30 years in top leadership roles as resort general manager and president, has died at the age of 68. Middleton was known for his love of the outdoors, community involvement, and dedication to growing Big Sky Resort into a premier destination.

Why it matters

Middleton's long tenure and leadership at Big Sky Resort was instrumental in the resort's growth and development over the past several decades. As a key community leader, he played a pivotal role in initiatives that shaped the town of Big Sky, from the creation of the resort tax to the founding of the local hospital and bank.

The details

Middleton started at Big Sky Resort in 1981 after leaving his hometown in Alabama and a business degree from the University of Alabama. He quickly rose through the ranks, becoming sales manager and then resort general manager and president, overseeing major expansions including the construction of over 20 lifts, two slopeside hotels, and the largest conference center in the state. Middleton was known for his hands-on management style, skiing every day, and mentoring dozens of employees whose careers flourished under his leadership.

  • Middleton started at Big Sky Resort in 1981.
  • He was named resort general manager in 1995.
  • Middleton became Big Sky Resort president in 2019.
  • He retired from day-to-day oversight in 2025.
  • Middleton passed away in February 2026 at the age of 68.

The players

Taylor Middleton

A 44-year veteran of Big Sky Resort who served as resort general manager and president, overseeing major expansions and playing a key role in shaping the local community.

Barbara Rowley

Middleton's wife, who joined him in making Big Sky her home and supported his many community initiatives.

Anna and Kate

Middleton's two daughters, who both worked as ski instructors at Big Sky Resort and are now professional ski patrollers.

Troy Nedved

Middleton's successor as Big Sky Resort general manager, whom he mentored in the role.

John Kircher

Middleton's predecessor as Big Sky Resort president.

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What’s next

A community commemoration of Taylor Middleton's life and legacy will be held on Saturday, February 28 at 2 p.m. in the Huntley Dining Room at Big Sky Resort, followed by a special on-mountain dedication at 3:45 p.m. and an après ski gathering at 4:30 p.m.

The takeaway

Middleton's long career and dedication to Big Sky Resort and the local community left an indelible mark. His passion for the outdoors, commitment to sustainability, and mentorship of countless employees helped shape Big Sky into the premier destination it is today.