Joy and gratitude define Taylor Middleton’s Big Sky legacy 

Hundreds immortalize ‘the single most influential person in the history of this resort and this community’ 

By Jack Reaney SENIOR EDITOR

When a community loses its hero, sorrow strikes everyone in unison.  

For seven-and-a-half days, Big Sky grappled with Taylor Middleton’s passing, an unexpected event beyond close friends and family. He was 68 years old, led an exceptionally active lifestyle, and was only 16 months removed from his 44-year career leading Big Sky Resort. He learned to ski at 23 years old, climbed from a seasonal gig to sales manager, and eventually from resort GM to his final full-time role as president and COO. When life-changing health complications presented what many would see as tragedy, Taylor Middleton saw opportunity.  

His courage provided closure on Saturday, Feb. 28 during Big Sky Resort’s celebration of life. The clear theme was Middleton’s gratitude and joy for all the life he lived, and for all he provided to his family, to Big Sky Resort and the Big Sky community since the early 1980s. It became clear that Middleton would not be defined by his untimely passing, but by his remarkable journey through life: his gritty, self-made career and passion for building community; his wandering “epics,” as he called his outdoor adventures; and his ability to pay attention to the things that mattered.  

“Joy and gratitude… Those were Taylor’s words at the end. I believe it completely, because a man who spent his life making other people feel capable and seen and valued has every reason for joy and gratitude,” said Troy Nedved, Middleton’s successor as resort president and COO, in a speech at the celebration of life.  

“Your life was the greatest epic of all,” Nedved said. “I’m still learning from you.” 

Many tears were shed by the hundreds in attendance on Saturday afternoon, but the lessons shared about Middleton discouraged sorrow, especially with widespread agreement that Middleton himself did not allow his ailing health to drag his spirit down. 

Rev. Miriam Schmidt emphasized how Middleton not only practiced joy and gratitude in his final days, but throughout his life. She emphasized the difference between enjoying happiness and optimism when times are good, versus the difficult task of seeking joy through challenging times, hardship and pain.  

“And that is what Taylor did. He practiced joy… leading this resort through economic recession, and avalanches, and COVID, and tragic deaths on these slopes,” Schmidt said. “Taylor chose to laugh, and love, and pour himself into all of life until the very end.” 

Stephen Kircher, president and CEO of Boyne Resorts, emphasized Middleton’s intentional and caring personality, both in his professional career and personal life.  

“He wasn’t the leader in the beginning that he was in the end—none of us are. But Taylor never stopped learning,” Kircher said. “… From the front desk, Taylor went on to become the single most influential person in the history of this resort and this community.”

In 2000, Middleton and Kircher set a goal to make Big Sky Resort the No. 1-ranked resort by Ski Magazine—a feat they achieved in October 2025. Kircher did not foresee the magnitude of the goal, or the way it would forge a friendship, or enhance an already great resort and community. 

“But Taylor did,” Kircher said. “He always saw further than most of us.” 

Nedved said Middleton’s leadership style fostered many more leaders within the community. He had a “teach, not tell” way of imparting wisdom. Nedved recalled Middleton’s penchant for asking “thoughtful, unhurried questions” meant to challenge a person and leave them thinking and questioning—sometimes for months or years.  

“He had a gift of drawing things out of you, that you didn’t even know were in there. He wasn’t trying to teach you anything… That’s the thing about Taylor’s influence: it had a slow release,” Nedved said. “He never told you what to think, he just created the conditions for you to figure it out for yourself. And that was a far more lasting gift than any advice.” 

Taylor allowed—and celebrated—mistakes and imperfection, Nedved explained. People felt safe to fail, learn and grow.  

One of those many homegrown leaders, ski school director Christine Baker, recalled a Taylor-ism: “Don’t let it be what it is, make it into what you want it to be,” she said in a joint speech with resort controller Courtney Jones.  

John Rolander, one of Middleton’s great friends and adventure buddies, described Taylor’s love for his daughters, for collecting rocks, arrowheads and petrified wood, and for enchanting kids in nature with his own childlike spirit.  

“There’s no doubt Taylor thought the greatest place on earth was Montana. He saw no need, ever, to go anywhere else,” Rolander said in his speech.   

PHOTO GALLERY BY JACK REANEY

Miriam Schmidt added balance, noting that Middleton could occasionally be frustrated, overcommitted or distracted. She said he would want to be remembered as a real person with real faults. “Then we’re not putting him up on some pedestal for doing what regular people can’t do. Then we are learning from him, even after his death.” 

Middleton’s oldest daughter, Anna, reflected on her special bond with her father. She noted he never judged, was unconditional in his pride and love, and provided endless support. Plus, she thrived on their adventures together.  

“He loved the most random places,” Anna said. “My mom, he and I all had our fair share of time accompanying him on Sprinter van trips to the quietest, flattest, hottest, windiest, least inhabited places… and he was so happy to be there.” 

With Taylor’s illness, Anna quit her travel-heavy job to spend more time close to home. She followed his lead, and saw the moment as an opportunity, not a tragedy. 

Her sister, Kate, wrote and recited a beautiful heart-wrenching poem.  

“I look forward, and you’re not there anymore,” Kate read. “I look backward, and my time with you is fixed. I can’t stop making plans for the past, so I settle uncomfortably in the present, and know that this is all you and I have… I may be young, but I know I’m lucky to have had what I’ve had for the time I’ve had it—the backyard, no shoes, a frog net and you.”  

Taylor’s wife Barbara Rowley kept it short at the conclusion of a long ceremony.  

“Nothing is simple and alone,” she said, quoting a verse she’d heard in a different community years ago. “The breathing mountains, the living stone, each blade of grass. The clouds, the rain, each star, the bees, the birds and the invisible spirits of the air. We are all one, indivisible, nothing that any of us does but affects us all.” 

John Zirkle led the choir during Middleton’s celebration of life. Asked to remember Middleton in just a few words, he recalled his “open-mouth smile” in a phone call with Explore Big Sky.  

“It’s really hard—he’s been such a core muscle for this community, ever since I’ve been here. I mean, he welcomed me, and so many people have that story,” Zirkle told EBS. “Like, Taylor helped me feel like Big Sky could actually be a home for me. And I think he did that for so many people, and I’m just really struggling to see how we’re going to fill that hole moving forward.” 

Zirkle and Rowley have led Big Sky’s theater and performing arts scene for decades. He remembers Taylor—a serviceable-at-best carpenter—putting in hours to build the set pieces ahead of Big Sky Broadway plays. Zirkle said he’d over-build everything to ensure the kids’ safety. 

“I was just always amazed at how he could kind of keep everybody moving ahead,” Zirkle said. “He really never stopped… I don’t think Taylor ever was bored. I never saw him bored, and I saw that come through while we were building sets together.” 

Madeleine Feher, now CEO of the Big Sky Community Organization, spent three years as his executive assistant in the early 2000s. She believes Middleton catapulted her career when he encouraged her to move on from that role.  

“Madeleine, you’re stuck in the box,” he told her in 2004, pointing to a simple, hand-drawn diagram. “You’ve gotta get out of the box.” She listened, and felt empowered to take on a new job in hospitality and seek growth outside of her familiar office.  

In general, Feher said Middleton was the epitome of an “authentic” and “classic” leader, always finding a thoughtful way to make an impact.  

“He was a trailblazer, without question. And he was such a supporter of us going out and getting involved in the community… He knew the impact that would have… And he did it as well. He walked the walk, and talked the talk, and didn’t ask us to do anything he wouldn’t do himself,” Feher said in a phone call with EBS. 

Nancy Sheil, now ski patrol director, knows the family well. She taught Kate and Anna in the Big Sky School District, eventually hiring both daughters to the ski patrol. She worked with Rowley on her Big Opportunities foundation. A fellow Alabama native herself, Sheil was inspired by Taylor’s southern roots as evidence of the ability for anyone to work their way to the top at Big Sky Resort. 

“He was maybe the most curious minded person that I know,” Sheil told EBS, noting his deep knowledge of the area’s history. “He was always interested in hearing more about something, whether it was history, or whether it was something happening at work. He would always be asking questions about it and approach it with a curious mindset.” 

His curiosity certainly extended to ski patrol, Sheil said. She praised Middleton for never letting his executive title impact the way he treated on-mountain employees.  

“He would just walk around the resort, and if he saw trash, he would pick it up. And if he saw somebody working, he would strike up a conversation. He was just very approachable and generous with his time and energy,” Sheil said.  

That feeling is shared by many, like Mike Foote, race director for the Rut Mountain Runs. 

“Taylor had a lot of responsibilities in his professional life. But whenever you were around him, he was paying 100% attention to you,” Foote told EBS. “So full of energy, and positivity and enthusiasm… And it helped you get excited to try bigger things.”  

Foote was always impressed by Middleton’s dedication to running the vertical kilometer event, especially because for many years, Middleton went straight to leading a Boyne Resorts state-of-the-resort presentation immediately after the grueling climb. He said Middleton was a big advocate for having a world-class trail race in Big Sky, and participated every single year through 2024—in 2025, he met finishers at the peak.  

“I can only hope that I can be as positive and welcoming and accommodating and active as Taylor was,” Foote said. “Because he had this energy about him.” 

Natalie Osborne, founder and race director of the Big Sky Biggie mountain bike race, said Taylor was one of the first leaders to say “yes” to the idea.  

“When Taylor got on board, it signaled to other landowners and partners that this event was worth believing in. His leadership helped open doors that may not have opened otherwise,” Osborne wrote in an email to EBS.  

Just like he did for the Rut, Middleton actually showed up. He rode for the first six consecutive years, through 2024. Osborne will remember him as graceful, grounded and quietly powerful with an infectious leadership style that supported Osborne during challenging moments. 

“When I once told him I wasn’t sure I could keep leading the event, he gently told me to stay the course and that if I didn’t do it, no one else would, and that the community was behind us,” Osborne stated. “… Getting a finish line hug from Taylor is one of the things I will miss most.” 

Tom Owen, owner of Gallatin Alpine Sports, often assisted Taylor in getting lost on his epics in nearby mountains.  

He listed some of the “infinite,” sunrise-to-sunset hiking and mountain biking adventures: Hyalite to Porcupine; Spanish Creek to Ennis Lake; Wilson Peak; Ramshorn Peak; Taylor Fork to who knows where; Cinnamon Mountain; Sage Peak. On summer workdays, shorter missions glorified the driveway access offered in Big Sky. In the winter, they swapped hardtails for skate skis and enjoyed the local Nordic track, or ventured into Yellowstone for classic-style tours.  

“We would hike and we would bike everywhere around us… He always wrangled me into doing the [Rut VK] with him—I never could beat him,” Owen said. “He was an amazing, strong athlete. He taught me a lot.” 

They shared their last bike ride on Gallatin Gateway pavement in October. Biking had become difficult for Middleton, but Owen knows he enjoyed it still. He said Middleton was a “beautiful, gracious human.” 

“The man’s energy and spirit was amazing,” Owen said. “The guy was always upbeat, he was always happy to see you, and he was always just bursting with a smile.” 

Taylor’s Trees 

After Saturday afternoon’s ceremony, hundreds of attendees jumped on Explorer Gondola for an on-mountain dedication.  

The word: meet at Tango Trees.  

There, on a cat track between iconic Mr. K and Crazy Horse in the historic center of Big Sky Resort, dozens of skiers gathered beside speakers blasting upbeat, throwback tunes.    

Middleton spent decades encouraging the resort to cut more glades. It was his favorite terrain to ski. Staff revealed Tango Trees would be renamed in Middleton’s honor. 

“It is very fitting that it is a glade run,” Kircher said.   

After a long moment of silence at 4:18 p.m., Anna and Kate assisted ski patrol in triggering an explosive on the Cue Ball just below Big Couloir. Kircher explained it as “a Big Sky version of a 21-gun salute—one large salute for Taylor, that the entire community will hear.” 

Before the boom echoed down to the meadow and across the many mountains Middleton traveled, it was heard by some 200 skiers. Kircher and Nedved rang the ceremonial Austrian bell, and Rowley beamed with pride as hundreds cheered and clacked their poles.  

The group dispersed around 4:30, skiing “Taylor’s Trees” with glee to the base area to be greeted by the thumping sound of après in the hazy Saturday sunlight. A lively pocket of culture in a must-visit, top-ranked ski destination, exactly what Taylor Middleton believed in.