Oliver Taylor Middleton was born in 1957 and lived his first life for 22 years as the second son of a main street merchant and timber farmer in the tiny town of Georgiana, Alabama.
He grew up playing and exploring in the thick woods outside his home, where he fished and hunted, rode motorbikes, shot cans on fence posts, and began working at the family grocery store after school as an elementary student. He loved to work; he loved to play; he loved to be outdoors, and he hated being bored. These four imperatives never changed.
He graduated from the University of Alabama in 1979 with a degree in business, the likely heir to operating his family’s retail and timber land interests, a fate he accepted without much enthusiasm. So when his college roommate called with news he’d be working at Glacier National Park, Taylor jumped at the opportunity to join him.
Taylor always said he “left the South running,” and it was true that he never looked back. When Glacier closed for the season, he headed towards Yellowstone, landing at an upstart ski area called Big Sky Resort, just entering its sixth year of operation. He joined the front desk staff at the Huntley Lodge and quickly ditched the deep Southern accent that had people erroneously calling him “Tyler.” He learned to ski at 23; to snowboard, telemark, Nordic ski, and most notably, mountain bike, in his 30s. His second life had officially begun.
After two years of working winters seasonally, Taylor knew for certain that Big Sky was his forever home. He nabbed a year-round job in the sales and marketing office and soon after was promoted to Big Sky’s sales manager.
Selling was easy for Taylor because he loved the product; his positivity turned clients and coworkers into lifelong friends. He often said that it was his prematurely gray hair and confident smile that persuaded group leaders and medical conference planners to take him seriously. The truth was, revenue was desperately needed to grow Big Sky, and Taylor was smart enough to know he was on the front-line to get it. A key strategy: Get Big Sky on every skier’s mental list.
In addition to successfully pursuing sales, Taylor worked hard to get Big Sky on the national map via magazines and newspapers. His success in this area – he lured dozens of national journalists to the resort for stories throughout his career – benefitted Big Sky’s reputation enormously, and ultimately, Taylor personally.
One such journalist, working on assignment for a New York publication, flew in for a four-day reporting visit in January of 1990. Her name was Barbara Rowley, and after quickly finishing the story, she returned just two weeks later at Taylor’s personal invitation. The two were married on Sept. 1, 1991.
In Barbara, Taylor found another lifelong passion – their marriage was his most valued partnership. In just a few years, the self-described Southern redneck had become a non-hunting vegetarian, a devout reader of The New York Times, and his wife’s best editor, advisor and friend. He instantly became the perfect dog dad to Jasper, and later, Smokey, Ollie and Billie, who all became his bike riding partners. He also agreed, somewhat reluctantly, to travel outside Montana at least once a year, having (post-wedding) surprised his new bride by claiming that there was no reason to ever leave the state.
Barbara quickly made Big Sky her home and began a futile lifetime effort to keep up with her husband on skis, bikes and trails as well as in his unending energy for do-it-yourself projects. Their marriage was a true union: she joined him for countless client and company dinners and resort events; he built sets for the children’s musicals she produced, and welcomed dozens of the young people Barbara mentored to their home - over twenty of whom lived with them for a season or two. Together, they worked and supported each other’s many community initiatives, from the creation of the resort tax to the founding of Lone Peak High School.
At the same time, Taylor’s portfolio of responsibilities within the company was growing, and so was his family. He became a father to Anna, his first daughter, in October 1995 while discussing with the doctor just how many helicopter trips it took to build the first Lone Peak Tram and welcomed a second daughter Kate, four years later.
In 1995, just as the first tram became operational, he was named as John Kircher’s successor as resort general manager, and later Big Sky Resort president as well, holding both top leadership and management positions for the next 24 years before leaving day-to-day oversight and becoming the area’s first president and chief operating officer, extending his impact company-wide across the now 13 resorts under Boyne.
During his long tenure with Big Sky, Taylor enjoyed countless days of perfect powder, and prided himself on skiing for a couple of hours almost every day he worked – on slope meetings were the norm. His co-workers were a vital part of his community. His career overlapped with the construction of more than twenty lifts (and two trams), two slopeside hotels, the opening of what was then the largest conference center in the state, and later the creation of Basecamp, the resort’s outdoor activity center, which together helped launch Big Sky into a true summer destination.
As a community leader representing what was for a long time the biggest employer in town, Taylor was often called upon to use his natural talent as an orator - he never read a speech. His state of the community presentations at the annual owners association meetings were legendary. He was pivotal in the creation of the Big Sky Chamber of Commerce and the drafting and implementation of the resort tax. He was a key player in the formation of the first Big Sky Transportation District and led the founding of Big Sky’s first bank and its only hospital, serving on each of these new entities’ inaugural boards (and many others). All of these efforts expanded his friend group across the community and southwest Montana.
To accomplish all of this, Taylor worked long weeks, days, and virtually every holiday – he believed in setting the right example from the top. He was known for managing by walking around: moving from the Huntley Lodge to the Summit could take him over an hour. He always said hello to absolutely everyone, usually by name, had to pick up any piece of trash, call in any problems he saw, and take the time to listen to any staff member or guest he crossed paths with. And, of course, he had to test out the snow, or the new trails being built in summer. He was often late for dinner and many winter nights fell asleep in his chair while answering emails.
Still, he prioritized being a loving, adventurous and fun-centric father to Anna and Kate, making sure that – like him – they would love to work, play, and be outside. He also made certain that they were never bored.
Together, they skied, rafted, hiked and biked; constructed bluebird boxes and installed them around the town, picked wild strawberries and raspberries, baked buttermilk biscuits, sought out eclipses, aurora borealis, comet showers, learned to unicycle, painted pictures, snorkeled behind beaver dams, hooted at owls, played board games and travelled their backyard, their state and their world with equal enthusiasm. His example was powerful: both girls worked at the company as ski instructors in high school and are now professional ski patrollers.
A curious citizen scientist, he insisted his family share his geologic, archeological and astronomical investigations, and treasured his days in the mountains learning names of plants, wandering slowly through the woods, and taking any opportunity to sleep under the night sky (even if it was on the porch, where he spent most summer nights). He had a legendary eye for finding arrowheads, crystals and fossils, and always brought home a rock as a souvenir from every adventure.
When he was promoted to Big Sky Resort president and COO in 2019, he relished guiding his successor and great friend Troy Nedved in his prior role as general manager, as well as continuing to mentor dozens of others whose careers had flourished at Big Sky, Boyne and other local businesses. During these years, freed from the on-site requirements of the day-to-day, he was deeply involved in the oversight, planning and execution of the Vision 25 plan which recently came to completion with the opening of the new tram and gondola, as well as the envisioning and implementation of the Forever Project, the ambitious multi-resort 2030 net-zero effort.
Despite his many hours at his desk, Taylor got outside every day, a habit somehow documented in The Wall Street Journal which in 2013 found his “epics” a newsworthy story for other executives. In winter, he Nordic skied by headlamp or got in runs before the lifts opened so he could reach his annual 100 days “on snow,” a goal he maintained through 2025.
Skiing trees was his favorite, and every year he directed mountain operations to glade more “hidden” runs across the resort. In summer, his epic mountain bike rides with a wide cast of his “adventure buddies” were never successful, he said, unless they got lost at least twice, returned home in total darkness and drank out of puddles.
Sweat was his friend: he loved putting on a jersey and racing, especially in the Rut and the Biggie, which he did every year until 2025. He kept a running to-do list of adventures over his garage workbench and when he transitioned out of daily operations and into the COO role, was able to take multi-week van trips throughout the Southwest, raft Grand Canyon, bike and hike in Spain, finally see Hamilton, and most wonderfully, take meetings on the Peloton or on a run.
Taylor worked for Big Sky for 44 years, three decades of them in the top leadership position. Looking back, he celebrated every moment of a career that met and exceeded his greatest desires, allowing him hard work, immense play outdoors, and the great satisfaction of leading a team and building a community.
Most importantly, he was never bored, or even disengaged, not for a single day of his life. In “retirement” he focused on fully living each day with family, friends and pet companions. For Taylor that meant teaching his girls to fix the broken heaters, plumbing and fences, and drive his beloved tractor in Gallatin Gateway. He loved his days of riding his bike around the pasture with the dogs, watching the birds, polishing rocks, cuddling the ever growing collection of barn cats, planting wildflowers, clearing the woods of brush, listening to podcasts, taking long naps in the sun, and reading and being read to by Barbara (a marriage-long tradition). He continued to ride bikes, hike and boat with a steady stream of visitors, often Boyne and Big Sky managers and their families, whose careers he had nurtured and in whom he took great pride. He slept outside every night.
Taylor loved his daily evening walks and ongoing conversations, reveling in the beauty of his first love, Montana, alongside his second one, his family. He often expressed how grateful he was for his final months in which he happily enjoyed more walks, more sunsets, more chances to hold one more arrowhead between his fingers, to hear one more hawk, win one more game, have more adventures with his friends and family visiting the rivers and mountains he loved and most importantly have the opportunity to be together.
Taylor never lost the genuine smile that he once thought was his only attribute, or the joy that lay behind it. He remained happy, busy, and filled with gratitude for the life he had always wanted and which, he said nearly every day, he was lucky enough to have actually lived.
For those who wish to honor Taylor’s legacy and life, consider donations to support the health of Big Sky’s environment, humans or animal companions with gifts to the Big Sky Hospital, Big Sky Bandage or RUFF. Donations to the Boyne Forever Foundation will be used both to help team members in crisis and to continue to fund sustainability efforts in his beautiful and most beloved Big Sky, his last – and very best – place.
All are invited to join in a community commemoration of Taylor’s life and legacy on Saturday, Feb. 28 at 2 p.m. in the Huntley Dining Room, followed by a special on-mountain dedication at 3:45 and an après ski gathering at 4:30. Arrangements are in the care of Dokken-Nelson Funeral Service. www.dokkennelson.com [dokkennelson.com]
