Longtime Big Sky President Taylor Middleton Dies at 68

Middleton, a southerner who didn’t know how to ski, helped shepherd Big Sky from backwater to global destination in his 45 years at the resort

An American story. Distinctly if not exclusively. An Alabama boy, loosed from college. Wandering Europe, Alaska, Florida. January ’81 he stumbles onto a sticks-and-stones amoeba of a ski area called Big Sky. A double-chair backwater, no snowmaking, no visitors. He can’t ski. It’s cold. So cold. But he stays in Montana. Not because he can’t find his way home, but because he’s found home. Within two decades he’s running the place. Big Sky aspires to its name. Spirals, sprawls. Up and out. He lays snowmaking pipe chain-hauled by bulldozer and devours bankrupt neighboring ski areas. Installs lifts that move like cheetahs and look like rocketships. Half a million skiers or more now. Valley floors cluttered with mansions, condos, SUVs, and egos. A Dixie farmboy 11,000 feet in the Western sky, commanding America’s third-largest and most sophisticated ski resort. He worked there for 45 years.

Taylor Middleton. A name like that, a legacy like that, conjures a strapping, obscene figure, swaggering and rattle-tempered, Hannibal’s-elephants-over-the-alps moxie with a machete in one hand and a fifth of Dadgum in the other.

But no. Middleton, who passed away on Friday at age 68, presented as humble, curious, and kind. His mannerisms and speech suggested a man who was delighted by everything and frazzled by nothing. My podcast conversation with him in 2022 was one of the most authentically engaged and unguarded that I’ve ever recorded.

Anyone can fake it for an hour. But Taylor wasn’t faking anything. When I met him in person a year later, he guided me down what he told me was one of his favorite runs at Big Sky: not one of the elevator shafts hanging off Lone Peak, but a mellow hill-and-dale blue-square tree run called Pomp, tucked inconspicuously away from Lone Peak and the hordes lapping Boyne’s armada of heated bubble lifts. “It feels like you just ski forever,” he told me.

That December, I returned with my family for opening day of Big Sky’s Willy-Wonka-and-The-Great-Glass-Elevator-style tram, a frantic, frenzied event in which the president of one of North America’s greatest ski resorts momentarily fortressed off the world to have this minute-plus conversation with my then-7-year-old son:

When I pick on Vail for funneling four general managers through Mount Snow in six years, Taylor Middleton is the alternate, better-case scenario I’m envisioning. Not because these rotating leaders aren’t qualified for their job, but because Middleton was not so much appointed to a job as given a title that matched his lived role in the community. A leader, embedded within a town and a ski area that he helped to create, fiasco-forged under the tutelage of John Kircher, a man so audacious and willful that he built a tram in defiance of the company CEO’s direct orders not to. So formed, Middleton’s gravitas was anchored not in title or mandate, but in his sheer ineffable presence.

In late 2024, Middleton semi-retired, handed off the president role to longtime GM Troy Nedved and took an advisory position for Big Sky. Well deserved, I thought. And unsurprising. “We need fresh blood and new ideas from people who are smarter and work harder,” he’d told me on that first podcast, when I asked why he’d handed off the GM role some years earlier.

But deciphering other’s motives is tricky, and of course I missed something. Almost exactly a year later, Middleton texted me:

The setup of the text was a little confusing - why send a written text telling me to listen to an audio text? But then I listened to the message:

In case you can’t access that, here’s what it says:

“Hi Stuart, it’s Taylor Middleton. I just wanted you to know that you’re helping people in a way that you never would have guessed. Not long after you were in Big Sky for the tram grand opening, I developed a slight slur in my voice, and gradually, over the next year, I lost my ability to speak entirely due to a neurological disease. Now, the good news: AI has improved artificial voices dramatically over the past year. The technology can listen to anyone’s recorded voice and replicate it. To build that new voice, the technology ideally has a lot of high-quality recordings to listen to. That’s where you come in. The interviews we did were the primary recording we used to build my replacement voice. I was already a big supporter of what you do, and now I’m grateful every day. Thank you, Taylor.”

A message both shattering and uplifting. The kindness of a man in decline, pausing to deliver unsolicited gratitude. I didn’t realize he’d be gone so soon after.

Unfortunately, we can’t measure men as we measure mountains. Big Sky is big and we can say so with tape measures. A man and his legacy are more complicated. Skiing’s first industrialized wave delivered easy heroes: Dave McCoy hammering Mammoth Mountain out of the fierce Sierra Nevada or Everett Kircher spinning a too-steep Michigan ridge into a continent-spanning ski empire. Middleton lacked that flamboyant path to legend. He became one anyway. That probably isn’t obvious to most skiers, at Big Sky or elsewhere, which is why I want to share this memo written by Boyne Resorts CEO Stephen Kircher and distributed to all employees (and forwarded to The Storm by one of them), in the wake of Middleton’s death:

R.I.P. Taylor. I hope those trees really do go on forever.