Rick Wilking/Reuters

The morning sun slanted through the windows of the Limelight Hotel, high in the mountains in Aspen, as Colorado Governor John Hickenlooper stood before the state's sheriffs at a conference in June. The Democrat was fielding questions about controversial gun-control legislation he'd signed the year before—legislation that this group had fiercely opposed.

"You made a comment about, sometimes to get somebody who disagrees with you to come over to your side, you just have to sit there and listen more, and you find that's a way to get them to turn to your side," said Sheriff John Cooke of conservative Weld County, referring to one of the governor's favorite talking points. "My question is, though, when these gun laws came up, why wouldn't you listen to the sheriffs? Why wouldn't, when a couple of sheriffs wanted to meet with you, you wouldn't listen to them and hear our side of the story?"

Your average politician would have had a well-rehearsed answer to that question; after all, signing the gun-control legislation 15 months earlier had been the most politically unpopular move of Hickenlooper's career. But Hickenlooper's stock-in-trade has always been that he's not your average politician—nothing of the kind—and so, characteristically, he winged it. "You know, I would say in, in the gun stuff that we, uh, certainly could've done a better job," he began, one hand jammed deep into his pocket as he gesticulated limply with the other. "And this is—I'm not defending this—there's no—I didn't find out that the sheriffs were trying to talk to me until a week afterwards—10 days afterwards. By that time, all the—whatever was gonna hit the fan had hit it." He scratched the back of his head. "I think we screwed that up completely, and I think we did a disservice to you and a disservice to ourselves."

When Hickenlooper's stammering apology went viral, it only hastened the slide his approval ratings have taken as he runs for reelection in November. The very qualities that allowed him to waltz into office four years ago, that made him America's best-loved swing-state governor in 2011 polling, have turned into liabilities. His self-deprecating style once helped defuse conflict; now his candid apologies open him up to fresh criticism. He once won voters' trust by refusing to talk like a "professional politician"; now his casual style is often considered amateurish, unserious—or worse. As he fumbled around for a way to connect with the sheriffs (dropping a jokey f-bomb that some found insulting), he made a most un-politician-like admission: He'd only agreed to sign a law barring high-capacity magazines because a staffer had promised legislators he would. "If we'd known it was going to divide the state so intensely," he said, "I think we probably would've thought about it twice."

When Hickenlooper was first elected governor, it was hard to imagine that his political charms could ever turn into liabilities. Voters adored "Hick," as he's widely called, to a cartoonish degree. Long before he became the mayor in 2003, Hickenlooper, who opened Denver's first microbrewery in 1988, had made himself an unofficial mascot for the city. As mayor, his approval ratings soared to 91 percent. His zany charisma alone seemed enough to carry his agenda, even when it involved tax increases; in one ad for an unpopular tax referendum, he jumped out of an airplane, declaring, "Voting yes ... will help lift us up," as he tugged open his parachute. It worked. Pretty much everything worked, even after he became governor in 2010. His mouthful of a name tripped off pundits' tongues as they wagged about 2016. Colorado Republicans struggled to find a qualified opponent to challenge him for reelection this fall.

But now he's locked in the most unexpectedly tight race of the midterms, against conservative Republican pundit Bob Beauprez, a former member of Congress and failed gubernatorial candidate. Two early-September polls found Hickenlooper leading narrowly. Quinnipiac, to the shock of talking heads everywhere, had him down by 10 points. He'd gone from a kind of political fairy tale—the centrist with the magic touch—to the most mystifying story in American politics.

Hickenlooper appears to exemplify just about everything contemporary voters say they want. He disdains politics as usual. He doesn't merely talk about problem-solving; he's actually brought opposing sides together on issues as fraught as fracking and taxes. Though he's nominally a Democrat, he's effectively nonpartisan. His policies and his staff pull from both sides of the aisle, and Hickenlooper keeps his party at arm's length. And as the sheriffs can attest, he's anything but over-scripted. He even fits the zeitgeist—the microbrewery owner who throws an annual tech and business summit to foster Colorado's start-up scene, the fellow you might have seen strumming a banjo on stage with Old Crow Medicine Show.

For an indie politician of Hickenlooper's stripe, this would seem to be a propitious moment in history. "Partisanship is less popular now than probably any time since the Progressive Era," says historian and writer Michael Kazin. Partisan loyalties are waning as more voters register as independents. In Colorado, about a third of the electorate is now unaffiliated. The flood of outside money into elections has made the support of a party less important. Plus, big, wacky characters are catnip for social media. Thanks to all those factors, Kazin says, "it's much more possible to be an independent personality ... someone who seems to be a figure who doesn't just not care about the parties but who thinks the parties are getting in the way of strong leadership."

That's Hickenlooper to a T. So how did the qualities that made him golden turn so quickly to dross? Political historian and columnist Eric Alterman, of The Nation, believes that some politicians fall for "a myth that we all basically agree on the issues, and we basically need to get together and do the right thing. But you can't govern on the basis of, 'You're a good guy; he's a good guy—you'll make good decisions.' "

Even so, Hickenlooper seems hell-bent on testing that approach. Although many candidates run as outsiders pledging to shake up the system—and never, ever to become one of "them"—most accommodate themselves to the status quo soon enough, morphing into predictable partisans with prepackaged sound bites. Hickenlooper, by contrast, has governed Colorado largely the way he promised. The story of his political rise and decline speaks to something larger, then: What happens when voters elect the kind of candidate they say they want, and he proceeds to govern as they expect? Do we really like leaders who refuse to play the game, who insist on thinking—even out loud and in public—for themselves? When Coloradans go to the polls in November, they won't simply be choosing a governor. They'll be offering answers to those questions.

* * *

On an August morning two months after his disastrous encounter with the sheriffs, John Hickenlooper is telling me the secret to overcoming the partisan divide. "I learned it in the restaurant business," he says. We're sitting in a back room of the Denver Performing Arts Complex, a palatial structure the size of four city blocks, and one that Hickenlooper helped to renovate as mayor. Today it's the site of his annual Silicon Valley-style extravaganza, the Colorado Innovation Network Summit, which starts in a few minutes. Hickenlooper leans back in his chair, thin and lanky in a camel-colored suit and pale-blue shirt (as usual, no tie). "You know, in the restaurant business, one of the things you learn is that if someone's very unhappy with their situation, you repeat back to them exactly what they're saying, in their own words. So," he says, leaning forward and staring me straight in the eye to demonstrate. " 'The waiter didn't look where they were going, and they dumped the soup completely on your lap, and the soup was very hot.' As they're saying those things, you repeat back to them, and they feel, you know, somehow heard and validated. And it makes them—it makes almost everyone—not so stuck on their point of view."

At 62, Hickenlooper retains a youthful restlessness—he's forever gnawing on a fingernail or scrolling through his BlackBerry—along with a haircut that flops boyishly onto his forehead. After 10 years in the mayor's and governor's offices, he still likes to bring up how much he's "learning"—about working with the Legislature, for example, or about why a particular issue riles constituents. At the same time, to hear him talk, he gleaned everything he knows about governing before he started doing it. Drawing on his five years in the energy industry, he lectures his staff on Bernoulli's scientific principle of "flow"—an equation that describes how fluid would move in a world without friction. This concept of effortless movement dovetails neatly with the main tenet he's imported from his brewpub days—that there's no percentage in making enemies. "Most of my philosophies come back to the citizen as customer in one way or another," he says.

Hickenlooper with President Obama at Wynkoop Brewery Co. in July. (Jacquelyn Martin/AP)

Like most politicians who succeed on likability, Hickenlooper has a backstory that fits his home state. In this case, it is the tale of a pioneer who went West. The oil industry lured him to Colorado in 1981. He was a 29-year-old Pennsylvania native fresh out of Wesleyan University, where he'd abandoned his dream of becoming a writer and earned a master's in geology. When the oil boom went bust five years later, he found himself out of work for 26 months. It goes some of the way toward explaining Hickenlooper's appeal that he speaks about this experience in as unvarnished a tone as he does his subsequent successes. "It does begin to create self-doubt," he says. "You look in the mirror at a different person. You relate to even your family and friends in a different way." But while he was bumming around at his brother's place in Berkeley, California, lightning struck: Hickenlooper enjoyed a pint at one of the state's first microbreweries and decided to take the trend to Colorado. In 1988, with money contributed by family and friends, he opened the Wynkoop Brewing Company, which became one of the pillars of the city's gentrifying Lower Downtown, or LoDo, neighborhood. Before long, he was opening a string of brewpubs across the country and becoming a multimillionaire.

Hickenlooper came to embody the idea that selling yourself is selling your product. He was not just the owner of the Wynkoop but also the fortysomething bachelor who offered a $5,000 bounty for a wife on The Phil Donahue Show, and the insouciant good-time Charlie who raced pigs through downtown Denver to mark his brewpub's anniversary. (Ever accommodating, he turned his "running of the pigs" into a "pleasuring of the pigs"—an orderly, on-leash procession—after People for the Ethical Treatment of Animals got involved. Then he called the whole thing off when they wouldn't leave him alone.)

Hickenlooper's first foray into politics was a campaign in 2000 to preserve the local football stadium's name, Mile High, instead of selling the rights to a corporate sponsor. In 2003, he ran for mayor of Denver. Colorado's municipal elections are nonpartisan, which allowed Hickenlooper to run solely on his own brand. He sold himself as socially liberal and fiscally conservative but, more important, as a plain-speaker who cared nothing for the stodgier conventions of politics. In one ad, he tried on a cowboy getup and an Uncle Sam costume while confessing that he had no clothes befitting a "professional politician." In another, he strolled downtown putting change into parking meters, criticizing his predecessor's decision to raise the rates as "just one example of what I call the fundamental nonsense of government."

Once in office, he revealed a knack for striking a deal and making people like it. Advisers like Tom Clark, a longtime friend who's the executive vice president of the Denver Metro Chamber of Commerce, warned him that ambitious regional projects would be a challenge because "the mayors in the suburban communities hate the mayor of Denver." The big city had always thrown its weight around. But Hickenlooper quickly distanced himself from his predecessors with small, astute gestures, such as declining to sit at the head of the table during meetings of the Metro Mayors Caucus. He neutralized tensions so effectively that when he wanted a light-rail system for Denver and its suburbs, paid for by a sales-tax increase that would usually be political poison, all 32 mayors signed on. Mayor Noel Busck of conservative suburb Thornton gushed to a reporter that Hickenlooper was "the best thing that's happened to this metropolitan region since sliced bread was invented."

While he was persuading voters to raise taxes repeatedly—for education, transportation, urban renewal, even prison reform—Hickenlooper also balanced the city's budget. He trimmed the number of government employees and cut salaries (including his own, by 25 percent). He seemed to have "tax-increase pixie dust," as the head of a free-market advocacy group that opposed the increases told The New York Times. The formula combined the mayor's bona fides as a fiscal conservative with the relentless—and creative—effort he put into public campaigns explaining why he wanted the money and where it would go. "Americans—Coloradans—are generous," he told The Times. "What they hate is waste."

When Colorado's term-limited governor stepped down in 2006, Democrats urged Hickenlooper to step up. He waited four years and ran as his party's anointed, without a primary, in 2010. He campaigned on economic issues—the state was facing a $1 billion budget shortfall, which he promised to tackle by overcoming entrenched divisions the way he had in Denver. His kooky ads attracted national attention, particularly one that has come back to haunt him in his reelection bid: In it, Hickenlooper was shown taking a shower, fully clothed, as he pledged never to run a negative spot. "I guess I'm not a very good politician, because I can't stand negative ads," he said as water sprayed him in the face. "Every time I see one, I feel like I need to take a shower." With former Republican Representative Tom Tancredo running a strong third-party campaign that doomed Republican nominee Dan Maes, Hickenlooper breezed into office.

Although he had run for the first time as a Democrat, Hickenlooper steadfastly remained a party of one. "Hickenlooper, more than any politician I've come across, is aware of his brand and talks openly with his advisers behind closed doors about his brand," says Colorado political analyst Eric Sondermann. "His staff, and he personally, [discuss] a whole lot of issues and ads in terms of, 'How does this conform to my brand?' "

Hickenlooper's first two years went smoothly, as governorships go. Because he knew very few of the state lawmakers before he arrived, he made time for meetings with all 100 of them. He handled his first great challenge, Colorado's massive budget shortfall, as adroitly as he'd promised, coaxing a balanced set of cuts through the divided Legislature. As always, he was popular. Though he had already started to develop a reputation for putting his foot in his mouth—a 2012 profile in Denver magazine included a scene at a memorial service where he told a joke that fell painfully flat—voters and lawmakers alike seemed inclined to forgive his slipups. "The very liberal legislators may be unhappy with John Hickenlooper, but almost uniformly they like him and will have a beer with him," says his chief political adviser, Alan Salazar. "Same with the conservative Republicans. It's one way of occupying the middle authentically, if you like people. And John likes people." That never changed during his term as governor. But before long, it stopped being enough.

* * *

In 2012, the worst thing that could happen to the Democratic governor of Colorado came to pass: Democrats, with turnout boosted by the Obama reelection machine, took control of both chambers of the Legislature. "The little pundit class out here," says Colorado pollster Floyd Ciruli, "that November, we all said the same thing: big problem." As Democratic lawmakers began to blaze through a wish list they'd been accumulating for years in the divided Capitol—not only gun control but also civil unions, marijuana, and strict renewable-energy standards—Hickenlooper's delicate balancing act became more difficult. On issues far more divisive than the budget, it was no longer possible to please all the customers.

When he joined the Chamber of Commerce in opposing Colorado's referendum to legalize marijuana, liberals and civil libertarians called Hickenlooper a hypocrite—pointing out the millions he'd made selling alcohol—and voters ignored him, approving legalization 55 percent to 45 percent. (Hickenlooper has since done a conscientious job of administering the law, most agree, but that hasn't helped his political standing.) The next year, when Hickenlooper decided to back a $1 billion tax increase for education, he made his case the way he always had in Denver. "I think the benefits far outweigh the costs," he said. "It's a chance for Colorado to be the No. 1 state for public education in the U.S." But the pixie dust had run out. Republicans had no trouble painting the hike as typical Democratic wastefulness, and voters buried it nearly 2-to-1.

Hickenlooper further alienated progressives with his support for hydraulic fracturing—a growing presence in the state, thanks to many of his friends, donors, and advisers from the energy industry. Last year at a congressional hearing, the governor famously testified that he once drank fracking fluid, to prove that its ill effects on health were exaggerated. When the city of Longmont banned fracking within its borders, Hickenlooper sued to overturn the law (he dropped the suit this summer as part of a larger compromise over fracking). Jonathan Singer, a Democrat who represents Longmont in the state House, says he likes the governor personally, but jokes, "That probably gets me in trouble with about half my voters." He believes that despite an eleventh-hour deal Hickenlooper brokered between anti-fracking Representative Jared Polis and fracking proponents, preventing dueling referenda from being on the ballot this fall, the governor will be haunted by the issue. "I talk to people who are withholding their vote from the governor even though he's passed some of the most progressive legislation in the history of Colorado," Singer says, "because he hasn't delivered to their standards, or frankly to mine, on one issue."

Hickenlooper with his opponent Bob Beauprez (Brennan Linsley/AP)

Still, no single issue altered Hickenlooper's fortunes more than gun control. He grew up in a gun-loving family—he often tells a story about accidentally shooting himself in the shoe as a kid—and in the days after the 2012 movie-theater massacre in Aurora, the governor told reporters he was skeptical that any regulation could have stopped the killer. But by the following winter, Hickenlooper had changed his mind. He settled on universal background checks as his top priority. He was convinced, he says, by the evidence that they worked. Plus, as he told the sheriffs in June, it struck him as the most likely measure to achieve consensus. "After the shootings in Aurora, as I went around the state," he said, "I kept hearing Republicans, Democrats, everyone, saying, you know, we should not take guns away from anyone, but keep guns out of the hands of dangerous people. I didn't think—this is how bright I am—I didn't think it was going to be that controversial."

After championing background checks, Hickenlooper signaled he would not support the many other gun reforms that Democratic lawmakers were floating. When he learned that 30 to 40 percent of fatal shootings of police officers involved high-capacity magazines, however, he got behind a bill to limit them. Gun-rights supporters were so incensed that they recalled two Democratic state senators and forced the resignation of a third. "There was a feeling in urban areas that magazines were associated with Aurora," says Christine Scanlan, Hickenlooper's director of legislative affairs at the time. But rural voters, by contrast, associated magazines with hunting. "The governor thought he could reconcile those two views," Scanlan says, "but it didn't happen that way."

This was becoming a theme. In 2013, Hickenlooper confronted his starkest decision yet: Would the governor, who'd expressed doubts about the death penalty, allow the execution of Nathan Dunlap, the so-called Chuck E. Cheese killer, convicted of murdering four people at an Aurora restaurant in 1993? To the dismay of just about everyone, Hickenlooper found a third way. Rather than sign the execution warrant or commute the sentence to life in prison, he granted a temporary reprieve, leaving the case open for his successor to reevaluate. Hickenlooper argued that although Dunlap did not deserve clemency, the death penalty is not administered fairly, so the governor was doing the honorable thing. "He found this very awkward [solution], what he thought was the sweet spot in between," says Colorado political consultant Eric Sondermann. "But there was no sweet spot." This summer, Hickenlooper reignited the controversy when he told CNN that he "could" grant clemency to Dunlap if Beauprez, who's pro-death penalty, beats him in November.

The governor of Colorado—or, rather, an actor who bears some resemblance to him from behind—sits in a director's chair, back to the camera, as two women comb his hair and apply makeup. "John Hickenlooper loves making campaign ads, but he despises making tough decisions," the voice-over intones. "Being funny on TV is nice, but unfortunately for Hick, governing is serious business." Released in September, this is the first Republican Governors Association ad of the season in Colorado. On screen, the faux Hick hands a stein of beer to a lackey. "It's time for a leader," the spot concludes. "It's time for Bob Beauprez."

Beauprez has built his surprisingly strong bid around the growing perception that Hickenlooper is wishy-washy and weak. "A successful campaign against Hickenlooper is, 'This guy is a good guy, but he's kind of a joke, and the challenges we face in this state are not a joke,' " says Republican operative and former state legislator Josh Penry. Sure enough, Republicans are working this fall to take all the items in the governor's "pro" column—his agile centrism, his genial frankness, even his beer—and turn them into "cons."

Maybe it was inevitable. Every strength is a weakness, as the saying goes, and even at the height of his popularity in his mayoral days, Hickenlooper was sometimes accused of caring too obsessively about retaining everybody's good opinion. "A couple of years ago," Sondermann says, "he was on all these lists of potential presidential candidates, and my notion was, 'I just don't see how this fits. In this politically polarized era, how does he appeal to the Democratic base, which fell in love with Barack Obama and is now pining for Elizabeth Warren and true believers?' And I don't know how it would work once he got there. If he can't make a decision on Dunlap, how's he going to make a decision on Syria?"

Hickenlooper bristles at such critiques. "We haven't been indecisive," he says. "We've made the most difficult decisions of all! Whether you're talking about capital punishment, or gun safety, or any of these things—we've been anything but indecisive."

That's arguable. What's not is the fact that Hickenlooper is—stubbornly—the same guy, the same candidate, he was four years ago. Yet the alchemy is gone. Why have criticisms of Hickenlooper that floated in the ether for years just now taken on weight? Perhaps it's because, in one sense, he did renege on an implicit campaign promise: the untenable pledge that he would always be lovable.

"If you're just running as a nice guy or a likable guy," The Nation's Alterman says, "you can win once that way, but then you have to choose." Choose a party, choose an ideology, choose a winning wedge issue—Hickenlooper stubbornly resists all that. Which brings him, this fall, to an uncomfortable pass: Having long ago repudiated negative ads, how does he counter the hits from Republicans? His response to the RGA ad was a clue to his strategy—and, for Democrats, not a promising one. In place of parachutes and showers, the spot that aired in September shows Hickenlooper waiting tables at the Wynkoop, repeating the same business maxims he has spouted his whole career. "First, money's always tight, so you make do with less," the voice-over says as Hickenlooper tallies a bill behind the bar. "And there's no profit in making enemies. It's why I don't do negative ads." The script is nearly identical to the talking points he used when he first ran for mayor in 2003—a message more befitting a political outsider than a man who's held office for more than a decade.

Until now, Hickenlooper didn't need ideological fire; he could fan his own exuberance instead. But returning to his old, colorful style of campaigning may not be an option this time. "I think those sort of eccentric ads, if anything, could be counterproductive," Ciruli says. "They could start a little wave of, 'Oh, God, not more of that.' It could enforce the Republicans' meme here, that this guy is not serious."

If Hickenlooper could go negative without being labeled—accurately—a hypocrite, the strategy would be a no-brainer, Ciruli says. "Do you know Bob Beauprez's position on reproductive rights?" he asks rhetorically. When Beauprez ran for governor in 2006, he said he would sign a bill banning abortion, with no exceptions for cases of rape or incest. Coloradans are far to the left of Beauprez on abortion, and the issue is a proven political winner in the state: It helped save Democrat Michael Bennet's seat in the U.S. Senate in 2010, and it's the heart of Senator Mark Udall's reelection campaign against Republican Cory Gardner this year. (Bennet is the brother of The Atlantic’s editor in chief and co-president James Bennet.) But Hickenlooper, despite his own support for abortion rights, hasn't gone there. (Democratic groups may, of course, attempt to do it for him.) "He's got himself in a very weird position," Ciruli says.

Hickenlooper is left to campaign on the broadly palatable elements of his record. He talks up the truce he managed to strike this summer between competing camps who wanted to float pro-fracking and anti-fracking referenda this fall—a genuine feat of political compromise that has produced no political upside. He talks, as always, about the economy, reminding voters that the state was in 40th place nationally for job growth when he took office and now ranks fourth. He touts his response to the unprecedented forest fires, droughts, and floods that have plagued the state during his tenure. ("Locusts are next," Coloradans have taken to saying.) It's not a bad record to run on, but it's no formula for revving up voters.

Weeks away from what could prove to be his first defeat at the polls, Hickenlooper finds himself trapped: between his positive pledge and the Republicans' negative campaign, between what voters say they want and what they actually seem to expect, between the longtime politician he is and the anti-politician he still wants to be. All of which has left him, as he travels the state trying to rekindle his old love affair with Coloradans, recounting the stories that folks fell for in the first place. At a lunch in July honoring the Agriculture Department's Colorado Proud program, dedicated to marketing local food, he re-tailored his classic tale about the Wynkoop and the pigs. "The bartender said, 'They should bring some local pigs next year, and people could see where their pork comes from!' So we actually, we roasted a pig on a spit out on the street, and then around the corner we had a pen with these little piglets. Oh my god, you would have thought that I had—." Hickenlooper shakes his head as the audience laughs. He doesn't have to go into the whole saga. Everyone here has heard it before.

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