The privilege and promise of Walker Stapleton: A Portrait in Four Parts

This is The Colorado Independent‘s complete four-part series on Walker Stapleton, Colorado’s Republican nominee for governor. You can click directly to Part 1 (Stapleton’s early years and family history), Part 2 (Stapleton’s business career and entry into Colorado politics), Part 3 (Stapleton’s time as state treasurer) or Part 4 (Stapleton’s run for governor).

You can also listen to reporter Corey Hutchins discuss his series on Walker Stapleton at our Indycator podcast. 

We’ve also written a four-part series on Stapleton’s Democratic opponent, Boulder Congressman Jared Polis.

 

Part 1: An elite East Coast background, a powerful family, and early political ambitions forged Colorado’s GOP nominee 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 cash 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.

“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.

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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.”

Part 2: Walker Stapleton’s short and winding road from business to politics

Walker Stapleton cites his business success as a reason to elect him governor. “I am fortunate,” he has said, “to have had a successful career in the private sector creating jobs, balancing budgets and building a successful company.”

The focus on his business background in ordinary years would be a sound strategy for a state that has proven it likes its leaders, particularly its Republican politicians, to come with some private-sector seasoning. But it’s a harder sell when running against a Democrat who began building multi-million-dollar businesses from the ground up when he was in college.

Stapleton’s career trajectory took a winding path. Upon graduation from Williams College, Stapleton took his master’s degree in business from the prestigious London School of Economics and then headed to New York and Silicon Valley in the midst of the dot.com revolution. After four years in two different jobs, he decided to go back to school. This time, he went for even more prestige, earning an MBA in 2003 from Harvard Business School.

After Harvard, he headed to Colorado where he landed a job at Lamar Companies, a private real estate acquisitions firm with an office in Denver. The job lasted a year when Stapleton left Lamar to join what became the family business. Four years later, he was running for state treasurer.

“Until I was in my early 30s I was focused squarely on having a business background,” Stapleton said in a May interview with The Colorado Independent. “All my education — my graduate degree, my master’s degree from the London School of Economics, my graduate diploma — all were in business-related activities and not political-related stuff.”

His first post-grad job brought him to Wall Street in his early 20s where he worked from 1997 to 1999 in the technology and banking division of the investment firm Hambrecht & Quist. From there he migrated to California’s Bay Area where he went into business development for Live365, the first radio community of independent DJs streamed on the Internet, where he worked from 1999 to 2001.

Live365’s then-chief technology officer, Peter Rothman, said in an email that he can’t remember how Stapleton landed the job. Back in those days, Rothman said, “Walker was a pretty young guy. He was a fan of the Grateful Dead and jam bands, but always wore a suit. We knew he was related to the Bush family and that was sometimes a joke around the office. I didn’t find him notably interesting.”

Steve Follmer, who at the time ran engineering for the company, remembered Stapleton as “genial, thoughtful, a bit bemused, perhaps even a bit awkward in large East Coast formal shoes.” He recalled Stapleton was hired “for his own qualifications, not his family background, which I only learned about after the fact.” One office memory he has involved Stapleton relating a story about a visit to the Bush family Texas ranch, wandering down into the kitchen in his pajamas, then “beating a retreat when he realized there was a tour coming through the house.”

Stapleton ran into the law during his time in San Francisco, pleading guilty to drunken driving after a June 1999 car accident. He “smelled of alcohol,” was “loud and belligerent,” and drove away from the scene, “initially refusing to stop even after officers arrived,” according to The Denver Post, which obtained the police report from Stapleton during his first run for treasurer. A hit-and-run charge was dropped, and he eventually did community service. A decade later, he told a reporter that acknowledging his DUI during a debate felt like “being forced to eat a doo-doo sandwich.”

Stapleton told The Colorado Independent in May that although he regrets the mistake he made in his early 20s, he doesn’t consider it a political liability. “If that’s the best that they’ve got … bring it on,” he said.

After his stint at Live365, Stapleton headed back East for Harvard Business School where he earned an MBA in 2003. From there, he moved to Denver and worked for about year at Lamar Companies, a private real estate investment firm. As director of real estate acquisitions, he was tasked with finding shopping centers, office buildings and other commercial properties on the West Coast for potential purchase.

Lamar CEO Mark Kalkus describes Stapleton as a diligent worker who found plenty of inventory but said the company didn’t end up buying any because properties were cheaper on the East Coast. “We just weren’t getting anywhere … He was frustrated not finding projects, we were frustrated we couldn’t buy anything,” said Kalkus, who supports Stapleton and has donated to his campaigns.

In 2004, Stapleton worked as a consultant for Castle Keep Realty of Denver, a private real estate firm, according to corporate filings with the Securities and Exchange Commission. Those filings also say he was a founding principal of Convergence Capital Partners, a private real estate opportunity fund that made investments in Eastern Europe.

Not long after he moved to Denver, he met Jenna Bertocchi, a magazine marketer, at a bar during a visit to New York City. He proposed at Walker’s Point, the Bush family compound in Maine, hiring a lobster boat with a “Marry me” banner. The couple wed at the Bush property a year later, in 2006, and nearly 700 protesters showed up near the church before the service, demonstrating against the war in Iraq and then-President George W. Bush, who attended the ceremony.

By the time of his marriage, Stapleton had upped his business credentials by being named chief executive and chief financial officer of Sonoma West Holdings in 2005. His family owned nearly half the shares of the California company he often notes was publicly traded on the NASDAQ.

His father, Craig Stapleton, a prominent Connecticut businessman and an ambassador during the George W. Bush administration, had joined the board of the former dehydrated fruit business in 1995. He built up his stock as it sold off its fruit operations to focus on managing and renting a handful of warehouses and light industrial buildings in California’s wine country. As CEO, Walker Stapleton would run the company from Denver with the help of a local property manager.

When Walker Stapleton was made CEO in 2005, company directors cited not just “his family’s long-term involvement in the management of the company,” but, among other things, “his extensive experience and expertise in finance and in the real estate industry,” according to corporate filings sent to company investors. That experience spanned six years, including his stints on the West Coast and in Denver.

Stapleton started out earning $96,000 per year in salary, but ultimately earned $431,000 in 2009, including a $210,000 salary, a $185,000 bonus, and $35,000 in other benefits, corporate filings show. That year, Sonoma West posted profits of $1.9 million on revenue of just under $3.7 million, both small figures for a company with public investors.

“When we were shareholders, and Walker was CEO, (Sonoma West) was not a significant enterprise,” said money manager Kent Rowett, a Californian, whose firm Leeward Capital owned more than 7 percent of the company at the time. He described Stapleton’s father as “the real economic engine of the company.”

As Rowett tells it, Craig Stapleton invested Sonoma West’s cash in MetroPCS shares when the wireless phone service was growing rapidly. The elder Stapleton sat on the board of MetroPCS in 2004. “He seemed to be well connected,” Rowett said.

Walker Stapleton declined multiple interview requests for this story. Craig Stapleton did not return messages left with an assistant at his office.

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New kid on the GOP block

Walker Stapleton was settling into life in the Denver area as a new husband, new father and new CEO when he began flirting with a run for public office in 2009. It was 17 years earlier that he had told his college newspaper of his itch to one day get into politics.

The 30-something with a double-whammy political name had joined civic groups, charities, and social circles with financiers and Republican heavy-hitters looking for winnable new leaders. The state GOP had some young rising stars on its bench, but its top-ticket candidates that election cycle ended up with serious flaws.

“We weren’t overrun with young interesting guys — or ladies, for that matter — in the Republican Party then who wanted to run,” said Sean Duffy, a public affairs specialist and former deputy chief of staff for Colorado’s last GOP governor, Bill Owens.

Stapleton was more than just a young, interesting guy. He had the name, the resume, the connections needed to be a viable candidate. The deliberative nature of the legislature wouldn’t suit his temperament, he told The Independent in May, so he eyed an executive branch role — the office of state treasurer. The job appealed to him, he said, because of his education and experience in finance. It also offered a potential launching pad; two former governors, Roy Romer and Bill Owens, had both been state treasurers.

No Republican had yet officially announced a bid to take on incumbent Treasurer Cary Kennedy, a well-respected Democrat who had shown a steady hand in protecting taxpayer money during the recession. In April 2009, Stapleton announced his candidacy, armed with a list of 30 big names and business people who supported him for the 2010 election. They included former U.S. Secretary of Veterans Affairs Jim Nicholson, El Pomar Foundation CEO Bill Hybl, and Gallagher Enterprises CEO Charles Gallagher.

Stapleton did not clear the field, and the early favorite in that year’s GOP primary race was J.J. Ament, now the CEO of the Metro Denver Economic Development Corporation. Ament had consolidated Republican establishment support as well as Tea Party backing, and he crushed it at the 2010 state assembly.

But Stapleton — who sidestepped the assembly process by paying signature gatherers to help him petition directly onto the ballot — out-fundraised Ament and campaigned hard. Stapleton’s early donors included George W. Bush and other family members, along with high-finance figures from New York to Texas, and some of his former Harvard Business School classmates. They also included heavy-hitters in Colorado. Pete Coors and John Elway chipped in. So did conservative Denver billionaire Phil Anschutz and Larry Mizel, a wealthy homebuilder and powerbroker. Robin Pringle, a vice president at Liberty Media who is now married to Democratic Gov. John Hickenlooper, was an early donor and is a close friend of Stapleton and his wife. Stapleton raised more than $500,000 and put at least $115,000 of his own money into the GOP primary race for treasurer.

He tagged Ament as a “debt-bond salesman” who was too closely tied to state government. And he cast himself as a political outsider and job-creating businessman.

Stapleton took on water in the race when he said in a TV debate that he wouldn’t oppose voter-approved tax hikes to help shore up the state budget. Ament stuck with the party line by flat-out objecting to new taxes and fees, which stoked suspicion about his opponent’s conservative credentials. Stapleton ended up narrowly beating Ament in the primary, aided by his hard work and money, impressing fellow Republicans along the way. “Walker was in a lot of ways seen as an outsider,” said Jesse Mallory, who managed Ament’s campaign and now runs the state chapter of the Koch-backed Americans for Prosperity, a national group that is helping Stapleton’s gubernatorial bid this year.

In the general election, incumbent Kennedy hammered Stapleton with ads about his DUI, calling him “reckless” and “irresponsible.” Asked in a general election debate whether he had his sights on a higher office, Stapleton said, “I’ll never become a professional politician. I’ll serve my time, speak from my heart, and then go back to my career in the private sector.”

Stapleton narrowly ousted Kennedy in what became the most expensive race for treasurer in state history, with each spending more than $1.5 million.

It turned out that 2010 was a wave year for Republicans. Yellow “Don’t Tread on Me” flags fluttered at political rallies, part of the backlash to President Barack Obama’s first term and the advent of Obamacare. Statewide, Republicans turned out some 100,000 more voters than Democrats.

“If there was a year to run for statewide office as a Republican, 2010 was the year,” said then-Colorado Republican Party chair Dick Wadhams, who had run campaigns for an older generation of GOP bulls such as former U.S. Sens. Wayne Allard and Bill Armstrong.

Just six years after moving to Colorado, Stapleton leapfrogged to a top spot in the GOP hierarchy without tying himself to Colorado’s Republican old guard nor rising through the ranks of conservative-issue politics, local government or the legislature. He didn’t have a ready-made political base of evangelicals, gun rights groups or the Tea Party.

Call it good timing or privilege, hard work or political promise, but with a combination of all, Stapleton had made a name for himself early in Colorado.

Financial journalist David Milstead contributed to this report.

Part 3: Pedigree and political ambition launched Walker Stapleton into the treasurer’s office, but state pension reform ‘put him on the map’

No issue has defined Walker Stapleton’s two terms as state treasurer more than his efforts to put Colorado’s Public Employee Retirement Association, known as PERA, on sound financial footing. After eight years sounding alarms about its solvency, fighting with the program’s beneficiaries, and suing board members, Stapleton can claim some victories.

“Walker has far more often been right than wrong on the PERA issue,” said Eric Sondermann, a political analyst who is co-director of the PERA-reform group Secure Futures Colorado. “But … he has often been a bull in a china shop.”

The state pension and health care fund, which affects more than 500,000 current and former public employees, has a $30 billion-plus funding gap that threatens the state’s bond rating and borrowing power. For nearly eight years as state treasurer, Stapleton has warned that without serious belt-tightening, the next recession could plunge PERA even deeper in the red.

Stapleton blames “out of control retirement entitlements” in the program, which is a substitute for Social Security for most public employees.

He’s called for freezing benefits, raising the retirement age — he has floated a figure as high as 70 years old — and hitting the snooze button on cost-of-living raises until the system recovers. He wants to change the makeup of the 15-member PERA board, on which he sits, so it has fewer plan beneficiaries serving on it.  If elected governor, Stapleton would have three appointments on the board.

During his first term as treasurer, he unsuccessfully sued fellow PERA board members to obtain the identities and benefit records of the state’s top retirement system beneficiaries. The move pleased conservatives and others, including Gov. John Hickenlooper, but rankled some retiree groups and PERA board members, who were personally named in the lawsuit. He ripped the PERA board for giving its executive director a raise for what Stapleton called “simply showing up.”

State lawmakers tackled some of PERA’s problems when they passed a measure in May to help pay off the fund’s looming shortfall over the next 30 years by forcing public employees to contribute an extra 2 percent to the pension, raising the retirement age of most future employees from 60 (or 58 for teachers) starting in January 2020, and by eliminating cost-of-living raises for two years, then cutting them by half a percent. Nearly all retirees in the plan will see cuts to their benefits.

Stapleton ended up supporting the measure even though the fixes to PERA didn’t go as far as his own proposals to shore up the fund. His proudest accomplishment during his eight years of fire and fury over PERA, he says, was persuading the board to twice lower the fund’s expected rate of return, which he still thinks is overly optimistic.

His PERA crusade endeared him to conservatives in the legislature and elevated his profile beyond the often-overlooked treasurer’s office.

“It’s PERA that put him on the map — his opposition and criticism of PERA,” said Bob Loevy, a retired Colorado College political science professor, about how the once-unknown Stapleton made his mark on the GOP political landscape.

Using PERA as a calling card also earned him critics who say he’s used the issue to elevate his political profile. Kent Willmann, a teacher for 32 years, said he was able to retire with what he hopes is a reliable safety net if the program stays solvent. He criticizes Stapleton, saying the treasurer has turned PERA into a wedge issue.  “He’s more interested in using it for political purposes than he is looking at it as a really good investment tool,” Willmann said.

Critics also say that for all his concern, Stapleton has a habit of skipping PERA’s board meetings and ghosting public debates about how to fix it. Records show he attended nine out of 11 meetings in 2015, four out of 11 in 2016, seven of nine in 2017. He said he listened in by phone or sent a proxy when he was absent.

Julie Friedemann, who represents school retirees on the PERA board, said she has yet to meet Stapleton personally in the year she has served on the board. She recalled a planning session in Colorado Springs prior to this year’s benchmark legislative vote. It bothered her that both Stapleton and his deputy were absent during a key part of a presentation on the plan.

“I would like a governor who methodically thinks through issues, is there for the debate, is there for the discussion, and hasn’t, as it appears, made a decision before everything has been discussed,” she said, adding that she was speaking only for herself, not PERA beneficiaries in general.

Ben Valore-Caplan, a Hickenlooper appointee who sat on the board for two and a half years as a Republican (he’s now unaffiliated), calls criticism of Stapleton’s absences a red herring.

“I do think that more than most board members, he was earnest in trying to raise this really core fundamental issue for the state — that this is not a sustainable business model,” he said.

But Valore-Caplan, an investment advisor, resigned in protest over legislation he said was pushed by Stapleton’s office during the 2015 session that, in part, could have refinanced some of the state’s debt to PERA by issuing pension obligation bonds — a financial move where a government borrows money at a low interest rate and invests it in hopes of a return higher than the borrowing cost. Stapleton’s support for the proposal, which would have given him the ability to issue bonds, ran into a buzzsaw among conservatives, talk-radio hosts, and limited-government groups who felt adding more debt was too risky. Americans for Prosperity, now a Stapleton ally in the governor’s race, ripped him that year, likening him to “liberal Sen. Michael Bennet.”

Stapleton eventually retreated from the proposal, saying he didn’t support it, despite having earlier testified in its favor. Some saw his reversal as politically expedient, and he did not get through the episode without some scars. “To hear Stapleton essentially say he didn’t support it, we were just stunned,” Americans for Prosperity’s regional director, Dustin Zvonek, said at the time. “There was no question in my mind he was in favor.”

Vincent Carroll, then The Denver Post’s editorial page editor, slammed Stapleton on the op-ed page, saying the treasurer sounded “like someone needing treatment for amnesia.”

Money in the market

After voters elected Stapleton in 2010, the first-time office holder made it a point to visit agency departments and toured all 64 county treasurers’ offices to learn how the state works and where tax money was going. He boasts of Colorado’s investments outperforming national benchmarks under his watch, and that he has helped businesses’ bottom lines by refinancing unemployment insurance and helped pass a bipartisan law saving taxpayers money by allowing counties to continue to invest in U.S. treasuries.

Stapleton declined repeated requests by The Colorado Independent for an interview for this series, but ask Republicans and Democrats what they think about his work and you’ll get what you might expect.

Republican Henry Sobanet, the former budget director for Democratic Gov. John Hickenlooper, said Stapleton’s and the governor’s priorities didn’t always align. “But our offices worked well together, and he had strong people handling the affairs of the office,” Sobanet said. “I did see Treasurer Stapleton dig in and learn about the issues over the years.”

Without Stapleton’s continued focus on the PERA funding gap, GOP state Rep. Bob Rankin from Carbondale said, “I’m not sure we could have done what we did this year.”

Democrats have accused him of frequent absences, not just from PERA board meetings, but from the treasurer’s office in general. They’ve pointed out that his statehouse parking spot is frequently unoccupied and that records tied to the key cards employees use to enter the building showed in 2014 that he’s had notable periods of inactivity.

Stapleton has said he accessed the building through a door in which key cards didn’t register and that his responsibilities managing the state’s investments have required him to attend meetings out of the office and throughout the state more than sitting behind his desk.

Questions about his attendance didn’t hamper his re-election. During the campaign, he touted that returns on the state’s $9 billion investment portfolio beat the national average. He defeated former Democratic Congresswoman Betsy Markey by nearly 10 points.

As treasurer, he has differed in some significant ways from his Democratic predecessor, Cary Kennedy.

Under Stapleton’s administration, Colorado no longer publishes a State Taxpayers Accountability Report, known as STAR, a program Kennedy launched in concert with the governor’s office and state controller. The initiative, which condensed hundreds of pages of the state’s publicly available financial statements into an easily digestible multi-page report, showed where money was coming from and where it was going, what Coloradans own, owe and buy, and effects of the state’s revenue-limiting Taxpayer’s Bill of Rights. The last one available is from 2011, and came from the state controller.

Rich Jones of the Bell Policy Center, a progressive think tank focused on increasing Coloradans’ economic mobility, said his organization relied on STAR to translate reams of financial data into something everyone could understand. “I think it did add to the transparency [of state government],” he said. “I think it would be helpful to be around.”

The STAR program no longer exists because the employee who compiled it under Kennedy left and the state controller took over the program, said treasurer’s office spokeswoman Rachel George. A spokesman for the state controller’s office said there was never any legal requirement to keep creating the report and says an online transparency initiative in state government might have made it redundant.

What to do with money in a roughly $1 billion Public School Permanent Fund was another area where Stapleton departed from the previous administration. Kennedy believed it was too risky to invest it in the stock market — and she told The Independent she still does. Stapleton thought otherwise, and supported a bipartisan bill to make it happen. He set up a board to manage the investments last year, marking the first time Colorado would put the money in the market (investing in individual stocks is prohibited, a board member says).

In addition to Stapleton, board members are John Hereford, partner in the Oak Leaf Energy Partners; Fred Taylor, president of the Northstar investment firm; Jackie Hawkey of the Black Creek real estate group; Greg Moffet, a Vail town councilman and state land board commissioner; and Peter Calamari of the Platte River Equity firm. All but Moffet are Stapleton campaign donors.

Moffet said it is too early to assess how the money is faring in what the board intended as a long-term investment strategy. “We have not gotten anywhere near that granular in our meetings as to what companies the funds are invested in,” he said.

So far, the fund has invested about $200 million in the market and has earned an additional dividend income of $1.9 million, treasurer’s office spokeswoman Rachel George said.

Over a few days in October, the stock market plummeted nearly 1,380 points. The state Constitution requires Colorado to make up any losses if the fund loses value, former treasurer Kennedy said. “Taxpayers are on the hook to backfill losses.”

George said the investment team told her that assessing the fund on a bad day for the market is not an accurate way to judge its health or the job the fund’s managers are doing. “In other words, these are long term investments,” she said. “It’s not like the people managing it are just day trading stocks like Amazon.”

While the public has heard little about the board and its investments, Coloradans know plenty about changes Stapleton made to another state program, the Great Colorado Payback.

In his first year, Stapleton decided the treasurer’s office should increase efforts to publicize the program, which urges Coloradans to check if they have unclaimed money from long-forgotten bank accounts or property from neglected safety deposit boxes. He aired TV ads during the popular March Madness college basketball tournament and doubled the number of claimants. The influx of claims swamped the office, which was still tracking claims by paper, and broke the voicemail system.

Complaints poured in for months. “It is ridiculous how long it is taking to get MY money back from the state,” one claimant wrote in an email to the treasurer in 2016. “WHAT’S GOING ON WITH MY CLAIM???” wrote another.

Stapleton acknowledged the problems were “absolutely unacceptable” after a Denver TV station investigated hundreds of pages of complaints in 2017. The issue bubbled up again in this year’s governor’s race. The progressive group ProgressNow paid for a billboard outside the Broncos stadium directing people to a website about the program where they can read complaints. And Democrats in the legislature called for an audit.

Stapleton has said he’s improved the program by assigning a new manager to run it, creating a digital system to keep track of claims, and involving a background-check company to help verify claimants’ identities. He has said the office has returned more property during his tenure than in all other years combined.

A matter of blind trust

In his first term as treasurer, Stapleton quickly came under scrutiny for his role at Sonoma West, a publicly traded California real estate holding company that he had run since 2005 and in which his family owned nearly half the stock.

He resigned as CEO after his November 2010 election and was replaced by his father, Craig Stapleton.

Walker Stapleton continued to moonlight for Sonoma West when he entered into a consulting agreement through a company called Rocky Mountain Trust LLC, of which he was listed as manager, according to filings with the Securities and Exchange Commission. Those documents show he would make $250 an hour, up to $150,000 a year, advising his father, managing tenant relationships, and participating in meetings and conference calls, among other duties. It is legal in Colorado for statewide elected officials to hold side jobs.

But public information on Stapleton’s arrangement ended when the Stapletons took Sonoma West private four months after Walker became treasurer and the company no longer had to file SEC disclosures.

“I don’t think Walker was very involved in the going-private transaction. I think he was already state treasurer at the time and couldn’t appear to be actively working on another job,” Kent Rowett, a Californian whose firm Leeward Capital owned more than 7 percent of Sonoma West at the time, said of Walker Stapleton.

It is unclear whether Stapleton has continued to augment his $68,500 annual salary as treasurer by remaining on Sonoma West’s payroll. When asked in September if he still works for Sonoma West, he said simply that he is an owner. And he told his neighborhood newspaper, “I’m not precluded from owning a business or taking a company private because I’m the treasurer of Colorado … It never took away from the hours I spent in the treasurer’s office.” In an Oct. 5 debate, he said he is not involved in Sonoma West’s management or day-to-day operations. He told CBS4’s Shaun Boyd in late September that he has “tried to make a conscientious effort to avoid conflicts of interest at all costs.”

Coloradans will have to take his word on that because Stapleton has put his assets into a blind trust. Elected officials, including Stapleton’s rival for the governor’s office, Jared Polis, commonly establish such trusts to avoid potential conflicts of interest by having an independent third party manage their assets. Blind trusts also allow officeholders to shield sources of personal income from public disclosure.

The public was able to get a sneak peek of Stapleton’s finances in 2009, before he set up his blind trust. In a personal financial disclosure filed with the secretary of state’s office when he declared his run for state treasurer, he listed his income and assets at that time. He reported he was drawing income from about a dozen companies, including Sonoma West Holdings, Denver Bank and Winston Partners Group. He also listed more than two dozen assets in which he had a financial stake, including Kroger, UnitedHealth Group, MetroPCS, Cisco Systems, and Wells Fargo. Some of the assets are current state investments.

Asked in a May interview if he still has sources of income beyond his state salary, Stapleton again touted his business acumen and responded: “You bet I do.”

Part 4: His last two elections were GOP waves. This year Walker Stapleton could be wading into a riptide

Walker Stapleton is no happy warrior on the campaign trail. Retail politics do not seem to come easily for the candidate who has spent eight years in statewide office as Colorado’s elected treasurer.

He can get fidgety and shiny under camera lights, and his voice can become agitated and combative, especially when responding to questions. He has agreed to some newspaper and TV interviews, but also rebuffed others, avoiding even small talk with some journalists seeking to cover his campaign.

“I don’t do extemporaneous interviews,” he told Patty Calhoun, longtime editor of Denver alt-weekly Westword when she approached him at a gathering of politicos in late August. “It doesn’t work out for me.”

That move left even some conservative pundits shaking their heads. “Who the hell runs away from Patty Calhoun?” asked Jon Caldara, head of the libertarian-leaning Independence Institute. “You insult her, she insults you back, and you go have a beer. It’s the way God wants everyone to be.”

In debates, Stapleton can get rattled, but he can also strike.

During one of his televised face-offs against opponent Jared Polis in early October, he struggled for 10 anguished seconds to explain the economic impact of foreign J-1 visas, stumbling over the numbers.  “…jeez,” he said when he finally got them right, “I feel like a kid in a spelling bee.“ But he has not held back from grilling Polis, turning to face him in debates, accusing him of a “radical and extreme agenda,” and demanding to know how he’ll pay for his free kindergarten, renewable energy, and universal healthcare plans. “You have no way to pay for any of this,” he said in the first debate, lecturing Polis about how the state budget works. “You are, sir, the all-star captain of debt,” he said in another.

Stapleton is known to have a good sense of humor, but his stabs at it on the campaign trail can also backfire. During an Oct. 8 debate in Pueblo, when Polis touted marijuana tax revenue being used for school construction, Stapleton drew jeers from the audience when he asked, “Does that mean you’d tell your kids to smoke weed for schools?”

Still, those who have watched him over the years, say his skill on the stump has improved.

“He’s not a natural campaigner,” said Ryan Winger, a Republican Colorado pollster. “And that’s all right, you don’t have to be a natural campaigner in order to win, it’s not the most important thing, it just tends to help. But I do think as a campaigner I think he’s kind of finding his voice and hitting his stride.”

Some friends and supporters say they wish voters had a better sense of Stapleton’s more relaxed and personable side.

Where the public might see a suited-up, ambitious young politician with patrician roots and a swank Greenwood Village address, they see a devoted father of three, a generous pal and a jazz fanatic. The Walker Stapleton they say they know wears T-shirts and shorts and enjoys kicking back with a beer at a Phish show or a ballgame. Four years ago, he invited a group to a 40th-birthday bash in New Orleans to knock around the French Quarter and catch obscure bands playing in dive bars.

“If everybody in the state [could] go sit down with Walker and have a beer and watch a band with him they’d vote for him,” said Josh Hanfling, a supporter, close friend and Democratic lobbyist.

That’s a sentiment echoed by Republican consultant Cinnamon Watson who recalled former presidential candidate Bob Dole’s campaign trail caricature as a grumpy old man, an image that crumbled after he lost and appeared in humorous commercials for Visa. “People were like ‘Why didn’t we see that side of him?’” Watson said. “I think people want to like the guy they’re voting for and I think Walker is quite likable. It’s not that the media has said that he’s unlikable, I just think that they haven’t demonstrated what he’s like in real life.”

After his reelection in 2014, Stapleton took several steps to position himself for a run for governor, developing a statewide reputation as one of Colorado’s most vocal fiscal hawks.

In 2013, he campaigned around the state against a proposed tax hike for schools. Then, when advocates for universal healthcare put forward a ballot measure in 2016, he became the public face of the opposition and toured Colorado debating its supporters. Author and former Washington Post reporter T.R. Reid was one of them. He describes Stapleton as a good-faith operator and effective speaker who understands healthcare policy. Reid said he enjoyed sparring with the treasurer, except for one thing. “He kept stating something false, and even when I corrected him, he kept saying it.”

Stapleton argued that if ColoradoCare passed, its board could later raise taxes. Not true, countered Reid, explaining that authority would rest solely with Colorado voters. But “he never gave up on this.”

The measure, which Republicans used to bludgeon Democrats on the 2016 ballot, lacked the backing of many leading Dems and went down in flames on election day. But it allowed Stapleton to raise his profile by leading the charge to defeat a Bernie Sanders-style, single-payer system that would have come with a massive tax increase.

In the lead-up to his run for governor, Stapleton also gained broader recognition in Colorado for his work with U.S. Term Limits, which seeks to cap the terms of elected officials at every level of government. He became the group’s pitchman in a 2017 ad campaign, and his name and face were plastered across TV and phone screens.

Before making his relatively late campaign announcement in October 2017, he worked to steer fundraising money to Better Colorado Now, a state-level super PAC now running ads on his behalf. Rules prohibit candidates from coordinating with PACs. But in a state with low limits on direct campaign contributions, Stapleton worked around those rules by raising money for the PAC prior to formally filing his candidacy. His cousin, Jeb Bush, pioneered the strategy in his 2016 presidential run, and was criticized for doing so. The Denver Post’s editorial board wagged its finger at Stapleton, writing, “We wish the treasurer had set a better example and not led us down this path — for others surely will follow.” Stapleton has called the criticism “political hogwash” and said he’s committed to raising the money needed to compete with multimillionaire Polis.

The Better Colorado Now super PAC has hauled in about $2.2 million with oil-and-gas companies ponying up to help fund it. Since the primary, Stapleton’s campaign has raised about $3.5 million, a little more than $1 million of it his own cash. Altogether, as of late September, outside groups, including the Republican Governors Association and the Koch-backed Americans for Prosperity, had ponied up $12.2 million to help Stapleton compete with Polis’s self-funding. Polis had put in nearly $20 million by September since entering the race.

Bush family members have given Stapleton thousands, as have members of the Coors family. The bulk of his campaign donors come from the financial, insurance and real estate world, according to the National Institute on Money in Politics. The Colorado Republican Party has given Stapleton $250,000 so far. Another fundraising apparatus called The Stapleton Victory Fund raked in about $1.2 million, with Walker’s father, mother and sister each putting in about $15,000 apiece. Leaders in the energy, construction and contracting business also gave big.

Those who surround Stapleton and help guide his political fortunes are a close group. His longtime campaign manager, whom he has called “the great Michael Fortney,” runs Clear Creek Strategies, a Denver consulting firm. A partner in that firm is Andy George, who runs the pro-Stapleton Better Colorado Now super PAC. George’s wife, Rachel, is Stapleton’s spokesperson at the State Treasurer’s office.

Despite the care Stapleton took in positioning the chess pieces for a future run for the state’s highest office, he overlooked details that were sure to come under scrutiny in a high-stakes campaign.

He failed to pay his property taxes on time in 2013, 2014, 2015 and 2016, racking up hundreds of dollars in delinquent interest, according to the Arapahoe County treasurer’s office. Stapleton’s campaign blames a refinancing and escrow account SNAFU and waves off the news as inconsequential. And while the issue hasn’t become campaign fodder, the optics don’t look good: Stapleton is, after all, in charge of the state’s finances.

What has become a campaign issue is his bungling of conflict-of-interest paperwork that involved income and asset disclosure.

From 2012 to 2017, and again in May of this year, Stapleton reported on a personal financial disclosure form that all of his income and assets were walled off behind a blind trust called Rocky Mountain Trust LLC.

Turns out that Rocky Mountain Trust LLC was not the name of his blind trust: Walker R. Stapleton Blind Trust is. The error came to light only after local news reports pointed out that Stapleton had “access and control” of Rocky Mountain Trust, which meant it was not a blind trust.

After the reports aired, Stapleton acknowledged he’d mistakenly been using the wrong name. Rocky Mountain Trust LLC was the name of the consulting company he’d set up to work with Sonoma West, the family company. His attorney, John Zakhem, dismissed the episode as little more than a clerical error caused by confusion over two names with the word “trust” in them. “The fact of the matter is the assets are in the blind trust, have been since that [2012] disclosure,” he said.

Jane Feldman, a former director of Colorado’s Independent Ethics Commission who has worked in ethics compliance for the New York legislature, said to her the issue shows a lack of attention to detail by the state treasurer. “My guess is Walker Stapleton didn’t sit there and fill them out himself …  sometimes I’ve had my taxes done by somebody else. I still review them to make sure there’s nothing wrong,” she said. She pointed out that in Colorado, the secretary of state’s office doesn’t review these forms to make sure they’re accurate or consistent, unlike some other states.

In the big picture, Republicans have embraced Stapleton as a well-qualified and electable standard bearer who can appeal to both alt-right-style Trump supporters and monied moderates, as well as someone whose record as a fiscal watchdog provides ready contrast to an opponent who promises big — and costly — policy changes.

Stapleton said his top priority, if elected, would be to rein in “out of control” Medicaid and retirement entitlements to shrink the state budget. His healthcare plan calls for waivers from the federal government so Colorado could offer different coverage options, including catastrophic plans that aren’t currently allowed under the federal Affordable Care Act.

He also aims to fund the state’s long-term infrastructure needs with bonds instead of new taxes. Stapleton has said he would be an advocate for business and fewer regulations, and he has focused his campaign around defending the state’s oil-and-gas industry from Democrats, environmental groups, and cities and counties that want to control drilling within their borders. His approach to making housing more affordable is to give developers the right to fix construction problems before they can be sued over defects. He wants more water-storage options as part of the state’s water plan, but hasn’t specified if that would include building new dams. If the legislature approves sports gambling, he said he would seek to tax the revenue and use that money to increase transportation funding. He supports randomly testing people on public assistance for drug use, saying, “If you are on the government dole, absolutely you should subscribe to random drug testing.”

He supports school choice, including taxpayer-subsidized vouchers for private religious schools, and calls himself a “numbers guy” who has been digging into public school data to show administrative costs are growing faster than costs for classrooms and teachers. He says he will “explore any avenue” to end so-called sanctuary cities, and he wants to crack down on medical marijuana cardholders and doctors who prescribe them because he thinks too many Coloradans are using so-called red cards to avoid paying the higher taxes on recreational pot.

Stapleton’s backers say he would likely run Colorado in a fashion similar to Bill Owens, a tax-cutter who governed from 1999 to 2007, and the last Republican to hold the seat.

“You won’t have a guy who’s just waving a bloody shirt and running around on the second floor with a meat ax,” said Sean Duffy, who was Owens’s deputy chief of staff and supports Stapleton. “He’s a guy who wants to make a difference.”

Duffy called Stapleton “a political realist,” who, if faced with a legislature divided between Republicans and Democrats, will figure out ways to get the work of the state done. “I don’t think he wants to sit in the corner office with a stamp and a veto pen.”

But first he has to get elected.

A purple state embrace of Trump and Tom Tancredo

Plenty of state and national political experts consider this midterm election a referendum on Trump. The president lost Colorado by 5 percentage points in 2016, and a blue wave could carry Stapleton out in a riptide. “By all appearances, this is a very, very tough political environment for Republicans,” said Eric Sondermann, a political analyst in Denver. “I believe he’s running in a light blue state in a dark blue year, and that’s what he has to overcome.”

This year’s election cycle began with assumptions that the Colorado governor’s race would be tight and closely watched nationally. But by August, two months after the June primaries, the race failed to make a Washington Post “Top 10 governor’s races” list. Jennifer Duffy, who analyzes gubernatorial races for The Cook Political Report, said she doesn’t see it as a toss-up in a year believed to favor Democrats, but it might also have to do with the candidates.

“I don’t know that either of them are the most charismatic people I’ve ever witnessed,” she said.

During the primary, Stapleton nearly blew it. He hired a firm to gather signatures so he could petition directly onto the GOP ballot and avoid the grassroots meatgrinder of the state assembly, where he’d have to appeal to the party’s most hardcore conservatives who choose the nominees.

But that plan blew up in spectacular fashion in April when GOP primary rival Doug Robinson accused him of hiring a firm that employed signature gatherers who lacked proper state credentials. Stapleton determined the allegations were legit and asked the Secretary of State to take his name off the ballot.

The only way to make it back on was to court votes at the assembly. He had about 90 hours to launch and execute an entirely new strategy.

In that scramble to re-calibrate his campaign, Stapleton did something that has dogged him ever since. He enlisted alt-right avatar and anti-immigration hardliner Tom Tancredo to nominate him at the Republican state assembly. Tancredo came with serious baggage, including his ties to VDARE, an anti-immigration online platform that counts white nationalists among its contributors. Tancredo said he agreed to help because he believed Stapleton could win a general election and was tough enough on his pet issue of ending so-called sanctuary cities.

The gambit paid off, and Stapleton snagged 43 percent of the assembly vote, 13 percentage points more than he needed to qualify for the ballot.

Stapleton’s supporters saw his handling of the ballot blow-up and his ultimate assembly coup as showing leadership, responsibility, and the ability to deftly navigate a crisis. His detractors said it showed mismanagement by a candidate who allowed his campaign to nearly implode and a willingness to tie himself to the alt-right in a mad dash to win.

Throughout the rest of the primary campaign, Stapleton embraced Trump’s tax policies and anti-sanctuary city stances. He aired TV commercials saying he would “stand with Donald Trump to get illegal aliens who commit crimes deported.” Polling during the primary race found enforcing immigration laws was a top issue for 43 percent of Republican voters, and Stapleton paid heed.

Since then, Stapleton hasn’t distanced himself from Tancredo, campaigning with him at a closed-to-media event in Parker over Labor Day weekend, the unofficial kickoff of the general election season.

Some of Stapleton’s allies said they wish he hadn’t embraced such a polarizing figure. The move particularly rankled supporter Jerry Natividad, a well-known Republican businessman and former chair of the Republican National Hispanic Assembly. Natividad said he sat down with Stapleton and advised him to stay away from the Tancredos of the world. “One thing that I have counseled Walker on,” Natividad said slowly, emphasizing each word: “This is not a red state anymore.”

During his general election campaign, Stapleton has criticized some of Trump’s policies, saying his tariffs could hurt the state’s farmers and his stance on J-1 visas could hurt Colorado’s ski industry. And, in a nod to the moderate wing, for his running-mate, Stapleton chose Lang Sias, a lawyer, Denver-area lawmaker, former Navy pilot and one-time Democrat who, like Stapleton, is from Connecticut.

Republican consultant Ryan Lynch, who helped guide Stapleton’s efforts through the assembly, lauded what he says is Stapleton’s success at unifying a once-fractured Republican Party in Colorado, especially in the age of Trump.

“Everyone focused on the Tancredo thing, but not what that meant,” Lynch said. “Unlike any other candidates we’ve had in a while, Walker was able to bring different factions of the party together. … not because of individual policy positions, but because they felt like they could trust him and they felt like he truly would represent the most people within the party.”

‘I think we’re going to be surprising people’

From Day One, Stapleton framed his campaign more about his opponent than about himself. Even in the primary he generally laid off his GOP challengers and zeroed in on Jared Polis, whom he correctly believed would win the four-way Democratic race.

He has continued that strategy, mentioning Polis repeatedly in stump speeches and airing ads entirely about him, despite some Republican grumbling that Stapleton should impart a clearer and more constructive image of who he is in his own right. They point to former GOP Gov. Owens, who won office by championing concrete ideas voters could easily picture, including the massive T-REX project that expanded freeways in Denver.

Even Stapleton’s children have noticed his preoccupation with his opponent.

At a recent swing through Walsenburg, Stapleton told a small crowd a story about his 10-year-old son, who asked to be paid for helping out with the campaign. Stapleton told him he could keep the money if he wins in November, but if Polis wins, the little guy might have to share with his two sisters and the rest of Colorado. “He looked kind of confused and said, ‘Dad, that really stinks,’” Stapleton said to laughs. “And I said, ‘Yeah, but those are the stakes.’” He said he overheard his son later tell his sister, “Coco, Jared Polis wants to tax kids.”

Stapleton’s challenge in these final weeks of the mid-term election will be to effectively define himself and avoid being dragged down by the national GOP, which is led by the most controversial president since Richard Nixon and which is expected to experience a backlash — especially from women voters — against the way its leaders in the U.S. Senate handled the confirmation of Supreme Court Justice Brett Kavanaugh. Unlike eight years ago, when Republican midterm voters were lashing back at Obamacare, Stapleton this time likely won’t have a Republican wave to ride. An Oct. 2 poll had him down by seven.

In a purple state that has trended blue in top-ticket races for two decades, Stapleton puts on a confident face as the anointed torch-bearer leading this year’s GOP cause.

“I think the race is pretty much deadlocked,” he told a voter standing on a sidewalk of Walsenburg’s main drag in late September. He said he expected support from healthcare and law enforcement groups that are “classically aligned with Democratic candidates. … So I think we’re going to be surprising people.”

And maybe he will.

After all, the GOP nominee with the double-whammy political name has been preparing for a race like this much of his life. He is the candidate the Republican Party says it has been looking for, and he’s running against a liberal Democrat from Boulder it long figured it could beat.

The promise of Walker Stapleton lies in one of the GOP’s oldest political calculations: that with the right background, the right connections, the right small-government, pro-business platform, and the right opponent, the Connecticut blue-blood could take back for the red team the privilege of running this purple state.

This is The Colorado Independent‘s complete four-part series on Walker Stapleton, Colorado’s Republican nominee for governor. You can click directly to Part 1 (Stapleton’s early years and family history), Part 2 (Stappleton’s business career entry into Colorado politics), Part 3 (Stapleton’s time as state treasurer) or Part 4 (Stapleton’s run for governor).

You can also listen to reporter Corey Hutchins discuss his series on Walker Stapleton on our Indycator podcast.

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