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

This is the final installment of a four-part series about Colorado’s Republican nominee for governor. Read part one, part two and part three.

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.”

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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. Republican power-brokers like Larry Mizel, a Denver homebuilder, and Phil Anschutz, the Denver billionaire who owns The Gazette newspaper and ColoradoPolitics.com among other major interests like The Broadmoor, have also chipped in. 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. Elected officials commonly establish such trusts to avoid potential conflicts of interest by having an independent third party manage their assets. Blind trusts also allow office holders to shield sources of personal income from public disclosure.

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.

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