The parade route is just two miles long, but not the way Walker Stapleton takes it. Like the energetic dog that runs up and down a hiking trail—doubling back dozens of times before reaching the summit—the Republican nominee for governor covers at least twice as much ground as the crew of politicos trotting behind him. He takes a circuitous route, and not purely out of enthusiasm for high school marching bands, extravagant floats, and all the pomp that comes with the annual Colorado State Fair Parade. There’s political capital at stake this August morning in Pueblo.

Stapleton darts back and forth across Main Street, gripping as many hands as possible. He greets eager children and expressionless cowboys, middle-aged women in camping chairs and old men in wheelchairs. He keeps a close eye out for police officers and veterans, beelining across the street to thank the men and women who protect and serve. He doesn’t seem to care he’s sweating through the back of his light blue button-up shirt. Sporting crisp blue jeans, brown cowboy boots, and a red and white “Stapleton, Sias for Colorado” trucker hat, he embodies the conventional look of a western politician.  

He occasionally hangs back to march alongside a massive Republican Party float. The 30-foot gooseneck trailer is covered in campaign signs—none bigger than the one fixed to the back, emblazoned with “Trump, Pence”—and pulled by a Ram 3500 flatbed owned by Scott Honeycutt, a rodeo veteran and GOP candidate for Colorado House District 62, which encompasses a large swath of southern Colorado.

Stapleton walks and talks with several state and local candidates, but makes special time for U.S. Sen. Cory Gardner, who came to Pueblo to support the Colorado Republicans on November’s ballot. Stapleton and Gardner work the parade crowd together, cracking jokes as they make their way to the finish. When Gardner hoists his daughter up on his shoulders, an impressed Stapleton tells him he’s the real pro on the campaign trail.

But Walker Stapleton is hardly an amateur. This isn’t his first campaign—the 44-year-old has twice been elected state treasurer—but it is undoubtedly the most important and most demanding. Stapleton has been on a breakneck pace ever since he announced his bid for governor in September 2017. He says running for the state’s highest elected office reminds him of grad school, as if each day he’s on deadline for another term paper. But rather than typing for hours, he’s crisscrossing the state in a red Cadillac Escalade, vying to become only the second Republican governor of Colorado in more than four decades.

By 11 a.m. when the GOP contingent finally reaches the parade’s terminus, it’s already approaching 90 degrees in Pueblo. Stapleton shakes only a few more hands before hustling away and heading north, where he’ll recover briefly at home before heading to a game at Coors Field.

Winning a statewide gubernatorial election as a Republican is a daunting task, and that’s why Stapleton has been everywhere in 2018. The campaign has 10 field offices throughout the state—from Grand Junction to Pueblo to Larimer County—and Stapleton has paid special attention to rural communities. He’s fond of saying he wants to be a governor for all of Colorado, not just for the population centers east of the Continental Divide.

It’s easy to dismiss that rhetoric as political posturing, but consider this: As the state treasurer—an office to which Stapleton was first elected in 2010 and re-elected in 2014—he visited all of Colorado’s 64 counties, attempting to develop a holistic vision for the state’s financial future. Along the way, it’s become clear, he says, that there is “definitely a growing urban-rural divide,” something Stapleton attributes to disproportional population growth in the Denver metro area. Smaller communities in eastern Colorado, as well as the most rural parts of the Western Slope, are “suffering mightily,” he says. Double-digit unemployment, lack of access to broadband, water rights, and inequitable transportation are the chief issues he sees as holding these communities back. In early September, Stapleton unveiled a rural Colorado priorities plan that aims to revitalize these areas—the significance of which is not lost on voters.

“A governor that understands I-70 goes all the way to Grand Junction is really important,” says Mesa County Commissioner Rose Pugliese, offering a refrain common among Stapleton supporters. Pugliese, an elected Republican who oversees economic development for the Western Slope’s largest city and for towns as small as De Beque (population 500), first met Stapleton in his inaugural bid for state treasurer. She says over the past eight years he’s endeared himself to communities west of the Divide and on the Eastern Plains. “Most people get elected on the Front Range in a statewide election, and they only come back out to Mesa County or the Western Slope when they’re up for re-election,” she says. “He came a couple of times a year, and we’ve been talking about rural issues for eight years now.”

Christian Reece, executive director of Club 20, a nonpartisan coalition advocating for the 22 counties on the Western Slope, is closely watching how the next governor will prioritize western communities. “One thing we really fight hard to do is bridge the rural-urban divide,” Reece says. “If we can get a strong advocate of western Colorado in the governor’s mansion, that only benefits the entire state.”

Club 20 doesn’t endorse candidates, and Reece is adamant that the organization remains politically neutral. For instance, she says outgoing Gov. John Hickenlooper “has done a phenomenal job in making sure rural Colorado as a whole is not forgotten.” But Reece says residents of the Western Slope are concerned they won’t be a priority if Stapleton’s opponent—Democratic nominee Jared Polis—is elected on November 6.

Some of those fears were stoked this summer when Polis, the U.S. Representative for Colorado’s 2nd congressional district, announced he wouldn’t attend the Club 20 debate in Grand Junction. He was the first gubernatorial candidate to skip the debate since it began three decades ago. While Polis’ campaign at the time cited a personal matter and scheduling conflict, Reece says that his campaign never communicated directly with Club 20, even after she reached out to see if he would reconsider. “People of western Colorado have a lot of concerns,” Reece says. “If  [Polis] is not willing to come visit Club 20, the oldest and most well-respected advocacy group in all of Western Colorado, then how is he going to partner with us if he is elected as governor?”

Because Polis skipped the September 8 debate, Coloradans missed their first opportunity to see both candidates square off. What would have been a headlining event at the two-day conference instead became a 24-minute, panel-moderated Q&A session with Stapleton, clad in a white dress shirt and blue blazer, on stage before a sparse crowd. Grand Junction’s Two Rivers Convention Center, packed hours earlier for the debate between Colorado’s candidates for attorney general—George Brauchler and Phil Weiser—was less than half-full by the time Stapleton took the podium and told the crowd “there couldn’t be a more important undertaking” than advocating for the economic future of western Colorado.

While Stapleton also expressed “disappointment,” that Polis didn’t join him that night, the two candidates debated in Grand Junction on October 6 at Colorado Mesa University. The two sparred—and found little common ground—on issues concerning energy, transportation, and water storage. Polis and Stapleton will take the debate stage twice more before the election, giving Colorado voters their last opportunity to determine where they stand on the issues, and also who they are as individuals.

With only three weeks to go until the election, Stapleton has positioned himself to win among Colorado’s rural voters, who are warm to his “all of Colorado” vision. Still, he is neither a rural man himself nor is he is a Colorado native—a label that has taken on undue importance in the Centennial State as more and more people transplant here.

Stapleton’s family legacy has been a subject of scrutiny ever since he announced his campaign. In particular, Stapleton’s claim that he’s a “fourth-generation” Coloradan has been disputed by the Denver media. In June, Westword ran a story that called Stapleton “a native” of Greenwich, Connecticut, a wealthy hamlet across the sound from Long Island. A week later, 9News aired a segment titled “Truth Test: Walker Stapleton’s a ‘fourth-generation Coloradan’ from Connecticut,” which said Stapleton was “born on the East Coast” and grew up in Connecticut.

In a phone interview in early August, Stapleton was quick to defend his “fourth generation” declaration. “I’m the fourth generation of my family to live in Colorado,” he says. “My kids will be the fifth, and anything else is a lot of semantics and hogwash.” He also took aim at 9News, which misreported the degree he earned at Harvard and, in Stapleton’s opinion, misled viewers. “The irony is that nobody fact-checks the fact-checkers,” he says. “The story that ran on 9News, first of all, said I was born in Connecticut (editor’s note: 9News did not explicitly say that). That’s not accurate. I was born in Washington, D.C.”

Stapleton’s family moved to Connecticut soon after he was born, where he attended private school before studying political science at Williams College in Massachusetts. He earned a graduate business degree from the London School of Economics in 1997 and completed his MBA at Harvard Business School in 2003, shortly before moving west. He met his wife, Jenna, in 2004, and the pair married in 2006. Before running for state treasurer, he served as CEO of Sonoma West Holdings—a real estate management company in which his family remains invested. The Stapleton family—which includes three children, Craig (10), Collette (7), and Olivia (4)—currently live in Greenwood Village, one of Denver’s wealthiest suburbs.

Walker Stapleton and his family at a campaign event in Greenwood Village in August. Photo by Jay Bouchard

Stapleton’s family ties in Colorado are indisputable, if not controversial. Walker’s great-grandfather, Benjamin Stapleton, served five terms as mayor of Denver from the 1920s through the 1940s, and is credited as being an advocate for major urban development projects, such as Red Rocks Amphitheatre and the city’s first municipal airport. There is even a neighborhood that bears his name. But Benjamin Stapleton is also remembered for his early affiliation with the Ku Klux Klan, despite splitting with and even working against the organization until he was effectively banished in 1925. Walker’s grandfather, Benjamin Jr., also worked in Denver politics, serving on the city water board and at the YMCA.

Beyond his family’s legacy, does it really matter to voters that Walker Stapleton was born and raised on the East Coast? “I don’t think it matters,” says Dick Wadhams, who has been active in Colorado’s Republican party for more than four decades, and whose family has been in Colorado since 1888. “Colorado has a long tradition of electing people to high office who were not born here,” Wadhams points out, referring to former Gov. Bill Owens (originally from Texas) as well as current Gov. Hickenlooper, who was born in Pennsylvania. “In a dynamic electorate like we have in this state, I don’t think people put a lot emphasis on it.”  

When the question was put to Stapleton, he said: “I think some elements of the media are more happy to care for it than the rest of Colorado.”

The media’s fixation on his roots highlights the fact that a candidate running a high-profile campaign has little control over how he’s presented—something Stapleton and his wife have both observed. “The funny thing is,” Stapleton says, “I’ve joked with Jenna that we both don’t recognize the character that’s been created of me in the governor’s race.”

The public eye is rarely able to capture the full humanity of politicians. And while Stapleton is no exception, upon closer look he is, at least, relatable. He harbors a love of music that goes back to his childhood, when he saw Miles Davis in concert while in fourth grade. Inspired, he took up trumpet and played in his high school jazz band; Stapleton cherishes his silver Stradivarius trumpet to this day. Before Jerry Garcia died, Stapleton made it to 32 Grateful Dead shows (he admits he doesn’t remember all of those equally), and he still seeks out live music in Colorado and across the country.

Stapleton also knows baseball. Though Jenna’s family are Boston Red Sox fans and their son, Craig, roots for the St. Louis Cardinals, Walker supports the hometown team. He often made time on the campaign trail to swing by a Rockies game, and was seen braving the chill at Coors Field on October 7, when Christian Yelich and the red-hot Brewers ended Colorado’s season. If you ask Stapleton who his favorite player is, he’ll make a passionate case that Nolan Arenado is the best—not just for the Rockies, but in all of baseball. And it’s not only the big stars he knows. At a campaign event in Grand Junction in September, when I arrived wearing an obscure New Hampshire Fisher Cats hat (the Toronto Blue Jays’ AA affiliate team), Stapleton immediately recognized the logo and bantered about players like Rafael Devers, who he saw play in the minors before making it to the pros.  

Baseball and music might offer Stapleton a broad connection to voters, but he’s making a case that, despite his elite upbringing, he is the most qualified person to lead Colorado into the future and—perhaps most importantly—to advocate for its rural communities. He’s a staunch supporter of the oil and gas industry, and has come out in favor of the Jordan Cove energy project, an ambitious but controversial plan to export Colorado oil—via Oregon—to Asia for the next two decades. Polis, on the other hand, has not taken a firm stance on the project, much to the ire of community leaders like Pugliese in Mesa County. Stapleton is also a strong supporter of the 2nd Amendment, despite not having any firearms in his home. And he’s racked up key endorsements from the Colorado Farm Bureau and from more than 50 county commissioners, many from rural communities.

Still, Stapleton has a tough race ahead in the coming weeks. In a bipartisan poll released October 2, Polis was leading Stapleton by seven percentage points. And in a second poll conducted by the Henry J. Kaiser Family Foundation released on October 10 (but conducted mid-August through September 19), Stapleton trailed his Democratic opponent by 11 percentage points. However, both polls showed a double-digit percentage of undecided voters and, according to Wadhams, Polis’ lead is likely not as large as the Kaiser poll indicates because independent voters in Colorado are so hard to predict.

Wadhams, who ran the 1998 campaign for Bill Owens, the state’s last Republican Governor,  thinks Stapleton stands a chance against Polis—but only if he’s able to win every rural vote and then some. “The brutal truth for every Republican candidate in a competitive statewide election,” Wadhams says, “is that you just have to blow away El Paso County, Weld County, Douglas County, and rural Colorado. By and large, in rural Colorado, you have to maximize the Republican advantage.”

But, Wadhams adds, “If it stops there, he’s not going to win this election.” Colorado’s nine counties with the most active, registered voters all sit east of the Continental Divide, and Wadhams says Stapleton has to earn votes in battleground counties across the Front Range—think Jefferson, Arapahoe, and Larimer, including suburbs of Denver as well as some of the Northwest foothills—if he has a chance at the governor’s mansion.

I don’t think I’m going to wave a magic wand and win Boulder or Denver County,” Stapleton says. But he does believe his policies resonate with enough Front Range voters that he’ll have a fighting shot to pick up votes come November 6. His appeal to Front Range voters, Wadhams says, depends largely on how he presents himself as a candidate—if he comes across as too extreme on immigration or other social issues, he could lose key independent voters (who account for more than one-third of the state’s eligible electorate).

Colorado Democrats have painted Stapleton as a conservative extremist, comparing him to President Donald Trump (who endorsed Stapleton in an early-morning tweet on October 10). Stapleton’s also been accused of avoiding the media, cozying up to white nationalist sympathizers, and maintaining a hard line on immigration and healthcare. But Stapleton pushes back, saying he’s a more dynamic candidate than how he is being represented. Though he’s come out against sanctuary cities, he says he supports the Deferred Action for Childhood Arrivals policy (known as DACA) and the Dreamers, undocumented immigrants who were brought to the U.S. as children—approximately 17,000 of whom live in Colorado. “I think we have to have a pathway for people who entered this country through no fault of their own and became contributing members of America to find a path to citizenship,” he says.

He’s supportive of what he calls “practical gun laws” that expand due process and reduce violence. He supports Colorado’s current mandatory background check system, he wants to find a way to keep firearms away from the mentally ill, and he would like to see metal detectors in schools. He’s also open to the idea of teachers carrying guns on a voluntary and well-regulated basis. “It’s not as though Mr. Roberts suddenly starts packing heat in AP history class,” Stapleton says. “It’s not like that. You have to go through training. It has to be locked away. There’s safety [precautions].”

Stapleton might not see himself as a far-right candidate, but he’s also hesitant to embrace the distinction of a “moderate” Republican. “I consider myself a pragmatist,” he clarifies. “I’m proud to wear the mantle of a conservative.”

The question remains: Can Stapleton reconcile his own version of himself with the character that voters have come to know? A guy with Colorado roots, an East Coast upbringing, and an Ivy League pedigree. A Front Range suburban dad with a sympathetic grasp on the issues facing Colorado’s most challenged rural communities. A guy with expensive suits and western boots, who can riff about the future of the Rockies bullpen in one breath and stress the urgency of fiscal responsibility in the next.  

No matter what happens November 6, Stapleton is going to need that kind of versatility. Asked what he plans to do on November 7, he says, “I’m going to pick myself out of bed and hopefully I’ll head down to the capitol to work on transition meetings. Or else, I’ll go on with the next phase of my life. I have perspective on this. And I have a skillset outside of politics in the business world.”

For the next few weeks, at least, Walker Stapleton’s business is politics. As the mid-summer heat fades and the first snowstorms move across the Rockies, hundreds of miles still need to be traversed in that red Escalade, and thousands of hands wait to be shaken by the candidate in the boots and cap, who is trying to bridge a divide that is, let’s say, more than just continental.

Jay Bouchard
Jay Bouchard
Jay Bouchard is a Denver-based writer and a former editor on 5280's digital team.