The privilege and promise of Walker Stapleton

This is the first in a four-part series about Colorado’s Republican nominee for governor. On Friday, Walker Stapleton’s business career. On Saturday, his time as state treasurer and, on Sunday, his campaign for governor. 

Walker Stapleton has steer snot on his hands. He does not look particularly comfortable with it, either, as he pats the animal’s head and runs a show stick along its belly in a dusty Colorado State Fair cattle barn. When a man from Oklahoma offers him a plug of chewing tobacco, Stapleton demurs. “If you want to be a real cattleman…” the man cajoles, trying again to no avail. Walker Stapleton does not want to be a real cattleman. He wants to be Colorado’s next governor.

That might not be easy.

If Stapleton wins Nov. 6, the two-term state treasurer would be only the second Republican in 43 years to occupy Colorado’s governor’s mansion. National analysts see him as the underdog in a swing state with increased Democratic Party registration and in a nation led by a divisive Republican. His opponent, Jared Polis, has a huge money advantage and has spent nearly $20 million of his own money since entering the race. Stapleton hopes that Polis is vulnerable on several fronts – he’s a progressive with a Boulder address and can be vague in answering how the state would pay for his ambitious policy proposals. The GOP nominee is relentlessly focused on depicting Polis as too “radical” for Colorado. 

If Polis is self-made and quirky, Stapleton is privileged and buttoned down. A youthful 44 with a dimpled chin and a full head of black hair, the red-Escalade-driving scion of two political families touts his record as a pro-business, anti-illegal immigration, mainstream Republican who has fought to reform Colorado’s underfunded pension system and keep a lid on taxes. To prevail in November, he is banking on his record as a fiscal conservative and supporter of Donald Trump’s tax plan and anti-sanctuary city policies. 

Stapleton, who declined repeated requests for an interview for this story, hasn’t helped himself by presenting an image that at times has been challenged by the record.

He calls himself a “fourth-generation Coloradan,” though he grew up in Connecticut and had lived here just six years before his first run for office in 2009. He campaigns as a financial steward for Colorado, but was penalized for paying late property taxes four years in a row.

There’s also the question of Stapleton’s job-creating credentials, which he touts on the trail without offering examples.  Before becoming state treasurer he worked one-to-two-year stints at an investment firm, a tech startup and a real estate company — along with some side gigs in consulting and investing — before being named CEO of what became his family’s real estate holding company.

At the same time, he counts as supporters former congressman Tom Tancredo and former governor Bill Owens, who represent opposite wings of the Republican Party. The president of the Denver Police Union supports him, as do more than half the state’s county commissioners and the Koch-backed Americans for Prosperity group. On Wednesday, President Trump tweeted his “complete and total Endorsement” for Stapleton, saying his “credentials and talents are impeccable.” Stapleton has raised about $3.5 million in his race, including more than $1 million of his own money.

Walker Stapleton also has something his opponent does not: A name long identified with Colorado and a political pedigree. The great-grandson of the controversial five-term Denver Mayor Benjamin Stapleton and second cousin to Jeb and George W. Bush has been steeped in politics and political ambition since birth.

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“Stapes”

Stapleton downplays his pedigree, scoffing at any notion that he is somehow part of a dynasty. “I also happen to be related to Chris Stapleton, the country music performer who sells out Red Rocks. Just because he’s my second cousin doesn’t mean that I sing like him,” he told his neighborhood newspaper, The Villager.

But Stapleton’s family’s political history runs deep and clearly played a role in his own ambition.

Stapleton’s mother is Debbie Bush Walker Stapleton, a cousin to former President George H. W. Bush. His father is Craig Roberts Stapleton, a prominent Connecticut Republican businessman who served as the U.S. ambassador to the Czech Republic and France in the second Bush administration.

Growing up in tony Greenwich, Connecticut, Walker Stapleton attended the private Brunswick School — known as ‘Wick among its alumni — where Craig Stapleton served as a board trustee and Walker’s friends called him “Stapes.” At the exclusive, all-boys prep school, students still wear coats and ties and annual tuition for high schoolers is $42,900.

In 1990, a young Walker served as a bat boy during a Texas Rangers game against the Oakland A’s — a perk that came with his father’s investment in the Texas baseball team with George W. Bush.

Two years later, he went to Williams College, a prestigious liberal arts school in the northern Massachusetts’ Berkshires where he was one of few conservatives on campus. Stapleton helped bring the conservative writer and National Review founder William F. Buckley to speak during his sophomore year. And he worked on The Williams Free Press, a fledgling conservative student newspaper. At the time, the mid-1990s, papers like the Free Press were popping up on liberal arts campuses to offer an alternative view and take swings at the liberal elite.

“That institution is politically correct to a fault, unfortunately,” Stapleton said of his alma mater on a Colorado talk radio show in March. “I think I definitely ruffled some feathers, I’m sure.”

Stapleton’s pedigree as a member of the Bush family was well known on campus. He campaigned for George H. W. Bush in 1988 and 1992 in nearby New Hampshire and served on the White House advance team, according to the student newspaper. “As for his own political aspirations, Stapleton said he definitely has been inspired by the rallies and conventions he has attended, and would like to go into politics in the future,” reads a 1992 article about him in The Williams Record. In 1996, the year he graduated, the elder Bush traveled to Williams to give the commencement speech.

Stapleton took an early shot at elected office while at Williams, beating his suitemate Chris Murphy — now the Democratic U.S. senator for Connecticut — in a race for freshman council, according to The Yale Daily News.

Back then, the young Stapleton’s politics and ideas weren’t all that memorable, said Mark Reinhardt, a political theory professor who still teaches at Williams. Reinhardt asked his students to make political arguments and work out their own views as part of their classwork.

“I don’t remember papers that were really the papers of someone who was writing as a conservative from the conservative end of today’s Republican Party,” he said. “He was as far as could be from abrasive and didn’t ever come off as an ideologue or anything like that. … I could use an old Bush expression: Walker seemed a sort of kinder, gentler kind of figure back in the day.”

Stapleton was also known on campus for his skills as a squash player. The Williams Record described him as a “freshman sensation.” His former squash team coach David Johnson remembered him as “an amazing competitor.”

Brett Hershey, who played on the Williams squash team with Stapleton and now is a theater professor in California, recalled him as a tough opponent who wouldn’t give up. The young Stapleton managed to eke out wins in ways that left spectators scratching their heads. “He would always hang in there,” Hershey recalled. “He was tenacious.”

Off the court, he remembers Stapleton talking plenty about politics on campus and spending time at the White House in the waning days of the first Bush administration. He recalls his phone ringing, Walker on the line. “He called me from the Lincoln Bedroom just so excited to be there.”

Hershey didn’t share Stapleton’s right-leaning politics. But he said they joked about their differences and shared some commonalities. One of their squash teammates was gay, Hershey recalls, admitting that back then he wasn’t so comfortable with the skirts his teammate would sometimes wear to practice. “There were a lot of discussions in the van riding to and from events,” he said. “I changed my mind and I think Walker as well became more tolerant.”

Hershey described Stapleton as a generous friend who helped him finance a movie project after college. It doesn’t surprise him that he’s now running for governor two decades later. “It seemed like he was going to do something like that,” he said.

Not everyone remembers him as fondly.

Mark Wolgemuth, now president of a technology company in Georgia, was in the same year at Williams as Stapleton and recalls him as someone who wasn’t shy about making his family connections known. “He had the whole, like, prep school ‘I’m-rich-my…relative-was-president’ attitude,” Wolgemuth said in a recent phone conversation. “As I recall him,” he added, “he just sort of kept to his small circle of suitable compatriots and made his way through.”

The Stapleton legacy

Three generations of Stapleton men before Walker have been wealthy and political.

Craig Stapleton, who is close with the Bushes, has been a businessman, foreign diplomat, baseball team investor — Texas Rangers, St. Louis Cardinals — and a member of corporate and governmental boards ranging from Abercrombie and Fitch to the Peace Corps.

Craig Stapleton’s father, Ben, founded the powerhouse Denver law firm Ireland Stapleton and served as a water adviser to Colorado governors. He was a friend and supporter of former Democratic U.S. senator and presidential contender Gary Hart.

But it’s the candidate’s great-grandfather, a Democrat named Benjamin Stapleton, who is known in Colorado history. Denver’s mayor in the 1920s, ‘30s and ‘40s, he was at one point a member of the Ku Klux Klan who appointed klansmen to his administration, including the police department, when the group dominated Colorado politics and even controlled the governorship. Benjamin Stapleton eventually distanced himself from the Klan as the KKK’s power waned in Colorado. For several decades after he left the mayor’s office, his legacy was tied mainly to having built city buildings, a highway, and Red Rocks Amphitheater. He was also the namesake of the old Stapleton International Airport, which since the opening of Denver International Airport has been redeveloped into a new urbanist community of about 25,000 people.

During Walker Stapleton’s first campaign for state treasurer in 2009, the then-six-year Colorado resident drew heavily on his family’s familiar name, speaking proudly in a TV ad about his great-grandfather’s accomplishments in Denver.

But this year, he’s not leaning on Benjamin Stapleton’s legacy to win votes.

In the eight years since he first ran for treasurer, civil rights activists and residents of the northeast Denver community named after him have started examining his great-grandfather’s Klan connections. Black Lives Matter 5280 organized a name-change campaign in 2015 that fizzled. Broader activism picked up last year, around the time Confederate monuments were toppling across the South following a deadly Unite the Right white supremacist rally in Charlottesville, Virginia. In the past year, the Stapleton Foundation for Sustainable Urban Communities scrapped “Stapleton” from its name, and the Stapleton Development Corporation voted quietly to call itself SDC, instead.

Stapleton declined to speak to The New York Times when it reported a story about this part of his family’s history in the context of this year’s governor’s race. The Denver Post followed up with a story headlined “Analysts: Walker Stapleton must be ready to deal with family skeletons as Colorado governor’s race heats up.” The coverage sparked a brief media skirmish. The conservative editorial board of The Gazette newspaper in Colorado Springs –  which supports Stapleton and whose owner, Phil Anschutz, is a campaign contributor – ripped the Times and Post as smear merchants.

As the Klan debate swirled around him, Stapleton said in May that he didn’t hear a lot while growing up about his great-grandfather’s Klan involvement and that his family isn’t talking much about that aspect of his life. Stapleton said he condemns racism and that it should be up to residents in the Stapleton community to decide what they do about its name.

“It’s 100 years ago, 30 years before I was born,” he told The Independent in one of his early public comments about the controversy. “If everybody started trying to apologize or explain what happened with ancestors of theirs who died 30 years before they were born, people would be doing a lot of explaining. I’m interested in focusing on the future.”

Asked during the primary if he expected his great-grandfather’s Klan legacy would come up in a general election if he won the GOP nomination, Stapleton said, “I’m sure whatever trash can be mongered will be mongered. I would say that the people that are most interested in mining that trash are people that wouldn’t support me to begin with.”

He said he had been in talks with community leaders including Denver Mayor Michael Hancock about ways in which to unite communities and not focus on the past. In a recent conversation with Independent columnist Mike Littwin, Hancock confirmed that Stapleton had reached out to him, along with others.

“I told him he should see this as an opportunity to discuss the issues,” the mayor said. “ … But obviously he didn’t take my advice.”

Not long after their talk, a Stapleton-supporting PAC came out with its “sanctuary cities” ad, which Hancock said he was “very disappointed” to see.

Stapleton in August declined to sit down with a reporter for this profile, saying he was unhappy with a guest post in The Colorado Independent by a writer who argued he bears a responsibility to address “the damage his great-grandfather’s KKK allegiance caused, not just to his family name, but to the citizens of this state.”

Nita Mosby Tyler, founder of the Equity Project, which helps Denver-area groups build diversity, said in September she does not expect the conversations about Benjamin Stapleton’s legacy to die down this election season, and that black communities are talking about it, especially in churches around Denver.

“If nothing else, the awareness about this past will mobilize voters to vote who might not have voted otherwise in this race,” she said. “If you attach some racial history to something, people wake up.”

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