Troy Downing, photographed in Big Sky’s Town Center.  PHOTO BY DAVID MADISON

Big Sky’s biggest name in politics

Troy Downing keeps making news in his bid to challenge incumbent Jon Tester
“I think we’ve gotten too big to be unincorporated. I think we need to have some sanity in planning and developing and making some decisions based on capacity of infrastructure.” —Troy Downing, candidate in GOP primary for U.S. Senate, who calls Big Sky home.

Like his ambitious run for the U.S. Senate, Troy Downing’s last paragliding experience began optimistically. 

“I took a paraglider and jumped off the top of Pioneer Mountain and was planning on making it down to the rodeo fields,” recalled Downing in a detailed, two-hour interview at the Lookout office, which sits just downhill from Downing’s current residence on the hillside overlooking Westfork Meadows. 

Back four years ago, Downing was living in the Yellowstone Club, where he launched the paraglide mission, hoping to float from the top of YC’s ski terrain all the way to Town Center. Things didn’t go as planned. 

“I ended up not having enough lift and crash landed in front of Sunrise Ridge and I broke my tailbone. I felt it crack,” said Downing, who was able to stand and start pulling his chute lines out of the surrounding trees. That’s when he noticed he had company. “I turned around and Yellowstone Club security is marching up the hill. They are in Delta formation. The guy at lead, stops, looks at me, shakes his head gets on the radio and says, ‘It’s Troy.’” 

Downing said YC security was responding to a concerned caller who reported seeing someone suspicious drop into the exclusive enclave from the sky. 

“Somebody had called saying people were parachuting in like ‘Red Dawn,’” laughed Downing, referencing the Cold War classic film about Soviet forces invading a small Colorado town. 

Lately, Downing spends his days barnstorming small and large towns across Montana in his bid to become the Republican candidate who runs against incumbent Democrat Sen. Jon Tester. It’s the loftiest of elected offices Montanans compete for and Downing’s sights on this seat has made him the most significant political figure hailing from Big Sky. 

Of course, Big Sky local politics swirls mostly at the school, tax and sewer district level, with heavy involvement from locals but little appetite for county or statewide office. Downing appears to be first aspirant from Big Sky to run for a seat outside the 59716 zip code. 

Looking for lift

On Feb. 5, the Associated Press ran the headline: “GOP’s Downing Outspends Senate Foes by Contributing Own Cash.” The story went on to report that Downing “whose U.S. Senate campaign is chaired by the wife of Interior Secretary Ryan Zinke has outraised and outspent his Republican opponents—but only by pumping $650,000 of his own money into the race, according to new campaign filings.”

Downing’s total war chest is somewhere between $800,000-$900,000, the AP reported, while Sen. Jon Tester has around $9 million ready to spend on his re-election bid. 

Whoever wins the GOP June 5 primary will receive massive support from outside conservative groups and the Republican National Committee, with estimates for total spending in this race predicting both sides will combine to spend as much as $80 million in the run up to the general election on Nov. 6. 

To win the Montana GOP primary, Downing plans to crisscross the state in a Chevy Suburban, giving stump speeches, shaking hands and collecting donations. At one event, an elderly woman apologized before handing over a $9 donation. 

“That is awesome,” said Downing, gushing about the inspiration he draws from visiting small Montana towns. 

“You just get this feeling that everybody’s got everybody’s back. You get that feeling of cohesive community. I love that,” continued Downing, who got an extra charge while visiting the tiny town of Loma, which sits just down the road from Big Sandy in the heart of Jon Tester country. 

In Loma, Downing felt strongly that, “The things I care about are the things they care about. Walking out of that event in Loma, I was on cloud nine.”

In Feb. alone, Downing has helped raise money for veterans with comedian Rob Riggle, he sat for an interview with Billings conservative talk radio host Aaron Flint, then he stumped in the Northeastern Montana community of Glasgow and attended the Montana GOP Winter Kickoff at the Radisson Colonial Hotel in Helena. The Kickoff’s “workshops will be focused on running a campaign, voter contact and outreach, data analysis, messaging, fundraising, communications and campaign finance laws,” according to 

Downing is a political novice, who like Sen. Steve Daines, Congressman Greg Gianforte and President Donald Trump, hopes to win over voters by playing up his success in private business. 

These days, Downing’s web calendar—a technology he helped invent—remains jam packed as his campaign picks up steam ahead of the June primary. Day to day, Downing supporters and detractors take shots on the letters to the editor page of Montana’s daily newspapers. 

A wave of anti-Downing letters appeared not long after the candidate was charged with multiple fish and game violations for allegedly purchasing in-state hunting and angling licenses while not living in Montana as a full-time resident. 

On Feb. 14, Downing’s case went to an omnibus hearing in Gallatin County Justice Court, just as the Lookout went to press. Downing characterized the hearing as “administrative” and vowed to keep fighting the charges. 

As for his out-of-state interests, Downing owns property in California, including a vineyard in Fallbrook near San Diego. He is also a part owner of a sock factory in North Carolina, but he adamantly calls Big Sky home. 

“My life is rooted here,” insisted Downing, who first put down those roots in 1998 when he started to explore the area. Then he moved into the Corral Motel while a crew from the Bitterroot Valley built his home in the Yellowstone Club. “I’m going, well, this is where I live, this is where I pay taxes, this is where my cars are registered, where I vote. When I came out of the military, I joined the Montana VFW.”

Downing’s military service in the Afghanistan included helicopter tours into combat zones to rescue troops. His campaign logo is red, white and blue in the style of the National Basketball Association logo, only for Downing the center of the image is a rescue helicopter. 

From ballet to battle

Downing’s journey to the cockpit of a rescue helicopter in Afghanistan started in Indio, Calif., where his grandfather homesteaded in a place “that used to be called Happy Valley.”

“If you wanted see if your neighbors were home, you got the binoculars out,” said Downing, who was the product of an unplanned pregnancy and was raised believing his adoptive father was his biological father. He’s now friends with his biological dad and marvels how he shares so much with someone he never knew as a kid.

“We both play guitar. We both play the same songs. We have a similar sense of humor and similar mannerisms,” said Downing. 

As a child, young Troy escaped into Gene Kelly and Fred Astaire films, dreaming of becoming a dancer.

“I hated where I grew up. I hated the desert. I hated the heat. Out of high school, I got about as far away as I could,” said Downing, adding, “I ran out of dirt on the East Coast.”

That’s where he enjoyed a brief dancing career, then contemplated a college degree in arts management. 

When asked whether or not past experience in ballet is a political plus, Downing said, “I absolutely own it. I danced in New York. That’s what got me out there. I was with the Ballet Theater of Pennsylvania. I was with the Connecticut Ballet. That’s how I paid the rent, from my teens into my early twenties.”

At New York University, Downing studied at the Courant Institute of Mathematical Sciences, which hired him as a research scientist while he was still an undergrad. 

“We had money coming in from Microsoft, Apple and Silicon Graphics,” said Downing. “Some of the things we did were really fun. It changed the way computer graphics were done, giving behavior to animated characters in very realistic ways. Like think the skin on the dinosaurs in ‘Jurassic Park.’ That came out of the research that was being done in the lab.”

The lab was also exploring what then was called “machine communication” but became the internet. Downing remembers asking a coworker “What do they call this?”, then hearing the word “browser” for the first time.  

Understandably, this is a major light bulb moment for Downing, who went on to author the best-selling “Web Publisher’s Construction Kit.”

“It did really well,” said Downing, noting how according to Amazon, it was one of the bestselling books of 1995. 

Downing started teaching classes at NYU and, “Things are moving fast. I’m busy.”

So he wrote a little application to keep track of his calendar. It would fax him a daily agenda every day at 6 a.m. It was an analog version of the little digital reminders that pop up on our smart phones today. 

But here’s the key: Downing programmed it so he could access his calendar from any web browser. 

As he thought more about his little calendar application, he started to realize how big it and the emerging internet could be: “This is huge. This is going to change everything.”

So Downing started a company called WebCal Corporation, which sold its services to any organization hoping to keep its staff coordinated with an online calendar. Customers included Exxon, U.S. West, then AT&T. He brought in friends from the lab at NYU to help take the company to the next level and the New York Times took notice. They called and interviewed Troy, who was turning his attention to another yet-to-break-out technology of the early 1990s: webmail. 

“And then this other company comes out—Hotmail,” sighed Downing. “Overnight, Hotmail was purchased by Microsoft for $400 million.” 

Troy missed his shot at selling a webmail service, but soon Microsoft called about WebCal. “That was scary,” remembered Downing. “Having the 800 pound gorilla come knocking at your door.”

But before cutting a deal with Microsoft, Downing first took a meeting with “these guys out in California.” 

“They had this directory that I didn’t like,” scoffed Downing, before laughing at how that directory soon became Yahoo!

When Downing met with Jerry Yang, David Filo and other Yahoo! staff in Santa Clara “we really hit it off.” Yahoo! was transforming itself into “a modern version of a media company” and they wanted Downing and WebCal to provide the “personal information management piece,” so he sold to Yahoo!.

That was the summer of ’98. A week and a half later, Downing was working in San Jose while also spending time in Big Sky. While in Silicon Valley, he was part of a venture capital team that funded 150 startups, of which many went bankrupt. But there were also big winners, including Google. 

“We seed funded Google. We were seed funders,” said Downing, cautious to over hype his role, which he characterizes as involved but minimal. “I was just one part of the team.”

Flush from tech investment paydays, Downing said, “I just wanted to find a place off the grid, someplace to be on my own, be close to hunting, be close to fishing, to skiing.”

By then, Downing said his focus was on Big Sky, so he settled in at the Yellowstone Club. 

Downing on local issues

Downing’s Silicon Valley background connects him with other members of YC. “There are other Yahoos here. And there’s a Google presence here as well. There are definitely people I’ve done business with in the tech field who are up here.”

If he should win the GOP primary, there may be a Downing For Senate office in Big Sky. The main campaign office is in Bozeman and Downing’s staff includes Lola Zinke, wife of the interior secretary. Downing also hired a consultant who worked with the John Kerry-sinking Swift Boat Veterans. And there’s a “finance guy” who helped elect Conrad Burns, said Downing. 

This past hunting season, Downing welcomed Eric and Donald Trump Jr. to a campaign event in the little town of Geyser. A photo circulated online afterwards—and depending on your political bias—was characterized as everything from awesome to unfortunate for Downing. 

When asked about Trump during a recent phone interview, Downing said, “I don’t want anyone to think I’m a rubber stamp for the president because I’m not.”

Downing’s Trump ties, the FWP charges and campaign skirmishes of the moment will continue to play out in detailed reports, but no one has asked Downing for his take on local issues facing Big Sky. So that’s what the Lookout focused on in its interviews with the candidate.  

Downing said he believes big Republican tax breaks will be a good thing for local businesses: “The small business owners in Big Sky can now increase wages, they can hire a new employee, they can increase employee benefits. They have extra cash to decide what to do as a business operator.”

As for the sell-off of public lands, he’s opposed to it, but wants “Montanans to decide what happens to lands in Montana.” He’s also against the proposed gold mine near Chico Hot Springs because it’s too close to Yellowstone National Park. 

What about incorporation? If Downing is for limited government, how does he feel about the complex idea of turning Big Sky into an official town?

“I’m going to make friends and enemies on this one,” Downing told the Lookout. “I think we’ve gotten too big to be unincorporated. I think we need to have some sanity in planning and developing and making some decisions based on capacity of infrastructure. Sewer and water is going to be a huge issue here, and if we just allow unbridled development, we’re going to get to the point where we don’t have the infrastructure that can handle the development.”

Downing said when it comes to more government and regulation locally, “There’s definitely two parts to that—the people who like the ‘Wild West.’ On the other hand, you end up with developers making all the decisions on how to plan a city and their interests are not necessarily in line with developing something that makes sense long-term. They’re interests are about developing and making money developing.”

What about the Big Sky Chamber of Commerce’s study into establishing a community council, which could exert Big Sky’s influence on the county commission?

“Maybe that’s a good first step,” toward incorporation, said Downing. “We need input. And we need to look at the realities of a quickly growing, quickly developing unincorporated area. If it just goes unchecked, we’re going to have long-term problems.”

Thinking decades ahead, said Downing, “You need to be planting trees in the shade you’ll never stand. What’s the future going to look like as it grows out. I’m a little worried right now that the development will outpace the infrastructure and we’ll all suffer for it. Starting with a council is great. We need to have some structure. Development here is just crazy. You try and get in and out during commuting times, it’s just horrible. All the way down the canyon there’s just trucks coming in every morning and going out every night. I mean, progress is great. Let’s make sure we’re doing it intelligently and with a goal of it making sense in the future.”

Downing acknowledges the call for “less rules, less regulation”—“That’s what I subscribe to in most instances.”

He said that attitude has helped give him “success, experience and skills outside of politics” and Downing wants that to be the core of his appeal. Again, it’s also Downing’s Trumpian side, something he heartily embraces now, but initially he wasn’t into the Donald.

“I was a late comer to candidate Trump,” said Downing. “I struggled with that a lot, but I’ve come around on it. I truly believe because he has a love of country. I look at his agenda and I struggle to find something I disagree with.”

At home in Big Sky

When he’s not touring the state trying to earn votes, Downing resides up the hill from the cluster of businesses on Snowy Mountain Circle. He walks down to Caliber Coffee—where a campaign sign hangs—to meet friends and fuel up on caffeine. 

Downing has a relaxed approach to storytelling, and you can imagine him holding court in coffee shops across the state. When asked about life in Big Sky, he might tell the story of when he came home with his family to find his home ransacked and a bottle of Jack Daniels in the middle of the living room. 

With his guns out-of-reach upstairs, Downing grabbed an axe for splitting wood and a fire poker.

“How stupid, here I am tiptoeing around the house with an axe and a fire poker,” laughed Downing as he recalled the story for the Lookout. Turns out, a bear was in the house. When it heard Downing creeping around, it ran out a door in the daylight basement. 

Had Downing and Sen. Jon Tester been seated together on a recent Delta flight from Salt Lake City to Bozeman, Downing might have told him the one about the bear and the Jack Daniels. As it happened, said Downing, he spotted Tester in first class and stopped for a moment to chat. 

“I saw him sitting there and I made eye contact and said ‘How’s everything going?’,” recalled Downing, who soon carried on to his seat further back in the plane. Tester’s campaign confirmed the encounter, saying because the senator flies back and forth from D.C. every weekend, he’s often upgraded to first class. 

At the time, Downing was returning from a trip to Las Vegas, where he met with Montana firearms manufacturers. Back in Montana, he resumed his travels across the state in his over-worked Chevy Suburban.

“A typical week is going from one corner of the state to the other,” said Downing. “We’ve already gone through one transmission and we’re putting in a new windshield today.”

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