Tim Alberta is chief political correspondent for Politico Magazine.

DES MOINES—The man knows how to make an entrance.

During his opening swing through Iowa after declaring his candidacy for president, at his very first campaign stop inside a bustling brew pub here south of downtown, John Hickenlooper arrives to find a crowd of more than 100 voters buzzing about the latest applicant to join the strangest job-interviewing process on Earth. Bending his lanky, 6-foot, 1-inch frame to fit through the crowded doorway of the events room, all eyes on the White House hopeful, the celestial nature of his moment shatters with the pint glass meeting the concrete floor just a few feet away.


It spawns something of a Zapruder film debate: Some attendees say they saw Hickenlooper fumble the glass, others insist he bumped into the man who dropped it, while the candidate himself swears he had nothing to with the accident. Whatever the real explanation, it’s less compelling than what happens next. Hickenlooper instinctively kneels and begins picking up the shards with his bare hands, shooing away staffers trying to stop him, and assuring them that nobody in this bar has more experience picking up broken glass than he has.

“He’s down to earth, that’s for sure,” says Pat Rynard, a prominent local Democrat who runs the blog IowaStartingLine.com. Sampling a flight of beers after Hickenlooper’s event, chuckling at the candidate’s idiosyncrasies, Rynard adds, “He’s going to be great at the retail politics.”

Anyone suspicious of Hickenlooper—anyone skeptical of a politician who acts as though he’s no better than the minimum-wage dishwasher called to clean this mess—soon finds their doubts allayed. Standing on a plastic crate in front of the room, his campaign’s “Stand Tall” signs plastered on the walls, the slouching 67-year-old starts telling stories. How his mother was widowed twice before age 40. How he had acne, coke-bottle glasses and no friends. How he moved west to work as a geologist, got laid off, then sunk every last penny into starting a brewpub in the abandoned lower-downtown section of Denver. How the community he longed for as an estranged kid—the community he found running the brewpub—prompted him to run for mayor. How his collaboration with Republicans in the suburbs created an infrastructure boom that attracted waves of businesses and young workers to the region. How he took the same approach as governor, sitting down the environmentalists and the energy lobby to broker the nation’s first agreement to regulate methane emissions. And how, watching now as a bunch of former class-president types jockey to lead a leftward-lurching Democratic Party, he can’t help but wonder if voters want something different.

Hickenlooper is certainly different.

Nothing about his appearance, from his rumpled shirts to the crooked row of bottom teeth to the untamed wisps of gray flopping over his forehead, seems especially presidential. He speaks in frenetic bursts, beginning one word before concluding its predecessor, his rhetorical pacing off-key like a garaged piano. Every question asked of him invites a story, often with no guarantee of a thematic circling back to the subject at hand. He says things like, “I’m not the smartest guy out there,” not exactly standard fare for an aspiring leader of the Free World. (Just for kicks, try imagining either Donald Trump or Barack Obama saying that.)

Former Colorado governor and 2020 presidential candidate John Hickenlooper (top right) stooped to pick up shards of broken glass (left) after someone dropped their beer at his campaign event at Confluence Brewery in Des Moines, Iowa this March. | Stephen Voss for Politico Magazine

The candidate’s friends call him “odd,” “quirky,” “eccentric.” For anyone who watched Hickenlooper’s recent CNN town hall—a prime-time event capable of jump-starting a longshot candidacy—these descriptors seem generous. When asked whether he would commit to picking a woman as his running mate, Hickenlooper said he would, then drew groans from the audience by adding, “How come we’re not asking, more often, the women, ‘Would you be willing to put a man on the ticket?’” (He clearly intended to highlight the historic gender imbalance in presidential politics, but the execution made him seem tone-deaf at best or pandering at worst.) Later in the program, Hickenlooper recalled the time he took his mother to see “Deep Throat” due to his ignorance of what the X-rating meant, setting social media ablaze once more and likely sending his campaign staffers scattering for the nearest cocktail hour.

Not that any of this should come as a surprise. The man who goes by “Hick” is an open book—literally. He told of the cinema adventure, and the unlikely moment of maternal bonding, in his 2016 memoir, The Opposite of Woe, and in that same book wrote extensively of his sexual undertakings, naming names and even describing in garish detail the efforts to lose his virginity. Anyone who knows Hickenlooper—anyone working for him, anyone endorsing him—cannot claim to be surprised by what unfolds over the remainder of the 2020 election cycle. To be exposed to him even momentarily is to encounter a mass of unfiltered dynamism, the opposite of stage-crafted and poll-tested, a living, breathing rebellion against the norms that once narrated our understanding of presidential politics.

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Sometimes Hick’s radical transparency can be painful to witness—and other times, it can be an absolute pleasure. Like when he volunteers the story, after being asked about combating climate change, of how he once took a swig of some fracking fluid to test the energy lobby’s contention that the liquid was not dangerous. Or when he doubles down on his assertion that his first move as president would be to sit down with Majority Leader Mitch McConnell, dismissing criticisms of his naiveté and arguing that the only way to heal America is by engaging those who seem least likely to reciprocate. Or when, sipping a stout in Des Moines while greeting voters following his event, he responds to a practical question about how to bring people together by hoisting his beer and shrugging his head sideways, as if to say, “A few of these couldn’t hurt.”

Hickenlooper was just 8 years old when John Hickenlooper Sr. died, leaving him with few pearls of fatherly wisdom. Some years later, he met Kurt Vonnegut, the celebrated writer, whom he learned had been a friend of his father’s. Vonnegut offered the younger Hickenlooper some advice that came to guide his life: “Be very careful who you pretend to be, because that’s who you’re going to be.”



***

Hickenlooper spent decades searching to find himself, emerging from a “broken” childhood into an adrift adolescence into an insecure young adulthood. He finally discovered the formula for happiness and isn’t going to change anything now. Hickenlooper has no need to pretend. He likes who he is. The question is whether voters will.

Hickenlooper speaks to a small crowd at his first campaign stop in Iowa, Des Moines’ Confluence Brewery, where he hopes to persuade early-state voters to back his moderate candidacy among a largely progressive primary field. | Stephen Voss for Politico Magazine

There is plenty to like: a trained scientist who quotes classic literature; a self-made multimillionaire whose business successes were interwoven with urban revitalization; a big-city mayor who was recognized as one of America’s best, fixing budget shortfalls and expanding public transportation by persuading Republicans to support a sales-tax hike; a two-term, purple-state governor who has real results to show for his efforts in expanding health care coverage, reducing gun violence, spurring economic growth and tackling climate change.

But presidential elections are beauty pageants, and Hickenlooper is hardly a knockout. Every speech he gives ends with the story of a rhetoric professor who taught her students the importance of contrasting opposites for emotional impact. “If you talk about the worst of times, talk about the best of times; if you talk about the agony, talk about the ecstasy,” he says. The punchline: When the professor asks her class, “What’s the opposite of woe?” one of her students yells, “Giddyup!” It’s good for a folksy giggle—at least, it is in Des Moines—with Hickenlooper using the story to illustrate how moments of sorrow are best met by getting back on the horse and charging forward. But it hardly carries the emotional weight of Obama’s hair-raising tale of the American Dream, the visceral resonance of Trump’s chant to build a border wall, or, in the case of 2020, the populist punch of Bernie Sanders’ crusade against economic inequality.

Whether he becomes a serious threat to win the nomination depends on whether he’s taken seriously—by rival campaigns, by voters, and above all, by the media. Surmounting a funny last name and made-for-gaffe personality is a tall task; it’s altogether towering as a moderate white man in a diverse, sprawling, progressive primary field.

Hickenlooper has his work cut out for him: In the latest Des Moines Register poll, not a single likely caucus-goer named him as their first choice, an insult that even the likes of Washington Gov. Jay Inslee and Montana Gov. Steve Bullock managed to avoid. These numbers are hardly relevant 10 months ahead of caucusing; and, if anything, a longshot candidate like Hickenlooper needs to rise slowly, gaining altitude below the radar and peaking at precisely the right time to stand a chance. But if that doesn’t happen—if his candidacy goes nowhere—it might just owe to the simplest explanation, already on the lips of the political class, that he is too odd, too quirky, too eccentric to be president.

Authenticity is a rare commodity in politics, and Hickenlooper has it by the barrel-full. The problem is that authenticity can be more of a burden than a blessing: For all the warnings against being prosaic, there’s a reason candidates give stump speeches and use talking points. The media—and the voters—expect politicians to act and talk and think in a certain way, at least when the lights are on. It’s much easier to assess a conventional, stick-to-the-script candidate than it is Hickenlooper, someone who speaks before he thinks, who overshares, who is unwilling to contort himself to fill a vacuum or meet a moment.

Ironically, the average voter is more like Hickenlooper than they are a cookie-cutter politician: accessible, openly flawed, imperfect with words, honest to a fault. Yet even in the age of Donald Trump, these characteristics are more often considered weaknesses than they are strengths; every candidate is still one YouTube clip from disaster. We know how to evaluate an Elizabeth Warren or even a Beto O’Rourke; we don’t know quite how to deal with a John Hickenlooper.

He probably won’t be the president of the United States. Maybe it’s because he’s too weird. Then again, maybe it’s because he’s too normal. Maybe it’s because he’s too much like us—flawed, offbeat, human.



***

On the journey to self-discovery, Hickenlooper hit a fork in the road at a place of maximum vulnerability: the unemployment line.

Raised in the middle-class suburbs of Philadelphia, the son of a steel mill executive and a sub-5-foot homemaker nicknamed “Shrimpie,” Hickenlooper became well acquainted with misery. His mother’s first husband, a heroic World War II pilot, died in an automobile accident, leaving her with two young children. She re-married to John Hickenlooper Sr. and had two more children, but he soon fell ill. What the doctors diagnosed as hemorrhoids was actually intestinal cancer, and the family watched him suffer a slow, excruciating death. What struck John Jr. as a child was how his mother would roll his father over in the middle of the night, every night, changing the sweat-soaked sheets; what strikes him as an adult, with the tears welling in his eyes, is how a wealthy neighbor who’d seen his mother lugging the daily loads of laundry to the cleaners surprised her by paying for a linen service to help the family.

1988 - John Hickenlooper, a former geologist by trade, with a couple business partners, opens Wynkoop, a brewpub and billiards hall, in the then-bleak lower downtown, or “LoDo,” region of Denver, which helped to kickstart the revitalization of the area.



1999 - 2000 - In his first foray into politics, Hickenlooper leads the community-based effort against a corporate sponsorship of Denver’s Mile High Stadium, arguing that retention of the iconic name was important to the city.



June 6, 2003 - Hickenlooper wins his first election, defeating more-favored local government insiders, to become mayor of Denver. In 2005, he would be named by TIME as one of the top five big-city mayors in the country, and, in 2007, he would be reelected with 88 percent of the vote.



Nov. 2, 2010 - A "dark horse" candidate, Hickenlooper becomes the first Denver mayor elected Colorado governor in over a century, winning by nearly 15 percentage points. He would be reelected in 2014, but by a much smaller margin. Mar. 4, 2019 - Hickenlooper announces his campaign to seek the Democratic nomination for President of the United States, saying, "we need dreamers in Washington but we also need to get things done. I've proven again and again I can bring people together to produce the progressive change Washington has failed to deliver."

It was this sense of “community”—a word he uses constantly—that he otherwise lacked. Children did not play at the Hickenlooper house. He was skinny, socially awkward and dyslexic. He also had a severe case of prosopagnosia, or face blindness, a rare condition that impedes one’s ability to recognize familiar faces. All of this made it nearly impossible to fit in. The resulting rebellious acts—fistfights, shoplifting—only fed his discontent, while fueling a terrible temper that consumed much of his childhood. “I was angry all the time,” he says. “Here’s my mother, she’s raising four kids by herself, and she would do the most innocent things, and I would go into a rage. … It started really when I was 7, 8, 9, and really went through until I was in high school.”

Although Hickenlooper finally did make some friends, he needed to escape the boundaries of his family and his hometown. He wound up in Connecticut for what he calls “that decade I spent in college” at Wesleyan University, first earning a bachelor’s degree in English and then, in a flash of the professional curiosity that would come to define him, a master’s degree in geology. Moving to Colorado to work for Buckhorn Petroleum as a geologist, Hickenlooper felt it was a perfect fit. He could explore, imagine, “lift over every new rock with suspense and exhilaration at what might lie underneath.” Instead, he found himself mostly behind a desk, doing lonely work, disconnected once more.

“When you’re a boy whose dad dies, you have to raise yourself to some extent. You feel abandoned by the world, and you’re looking for a sense of community,” Hickenlooper says. “Those are the two things I took from my childhood: a yearning for community, and an empathy for people who are hurting and marginalized.”

As if cued by a cosmic bolt of lightning, he suddenly lost his job. Buckhorn Petroleum was bought out and its employees were laid off. Hickenlooper might have felt relief if he weren’t so panicked. Abruptly unemployed in mid-30s, with no family of his own, he began to question his purpose in life. “When you’re out of work for a while, you really start to see a different person when you look in the mirror,” he says. “All change involves loss, and all loss needs to be mourned. But change is often a very good thing.”

Hickenlooper liked geology and initially hoped to keep working in the field. But he came to see the firing as a blessing. No longer would he settle for solitude. Thinking about other things he liked—drinking beer, being around people, drinking beer while being around people—Hickenlooper hatched a crazy plot: He would start a brewpub, part brewery and part bar, with a full-service restaurant to boot.

It was pure fantasy. At the time, he says, the craft beer craze hadn't yet begun—fewer than a dozen brewpubs were operating in the U.S. and none of them in the Rocky Mountain region. But Hickenlooper had a hunch that he was onto something big. Borrowing a local library book on entrepreneurship and working feverishly with a friend to raise money $10,000 at a time, he built a business plan.

It didn’t exactly inspire potential investors. For a time, Hickenlooper’s dream appeared unreachable. Salvation came in the form of a loan from the city of Denver and cheap real estate: The area known as lower downtown, or “LoDo,” had turned into an urban wasteland, blocks of abandoned buildings haunting the landscape. One of them, a five-story mercantile warehouse with a basement that once housed supplies of molasses and fabric, was offering rent that was practically free. Hickenlooper was enchanted by the building and urged his business partners to pull together every last one of their resources and finally take the leap. In 1988, renting the building for $1 per square foot, they opened the Wynkoop Brewing Co.

“I thought I was a good geologist,” Hickenlooper recalls. “But my first day in the restaurant, dealing with the customers and the cooks, I felt at home.”



***

We’re standing in the basement of the Wynkoop, just outside the room where a hulking, metal contraption processes grain, and Hickenlooper is acting out a story about the time when he stuck his face in a toilet caked with hardened feces.

These were the early days of entrepreneurial hardship, pinching pennies and gutting out whatever tasks came his way. In this case, when a friend offered “beautiful, old, art deco toilets” for $10 apiece, Hickenlooper pounced, not realizing they were in a building with no running water and therefore choked with years-old excrement. He was undeterred: On moving day, Hick got down to lift them by the base, one by one, proving his maniacal commitment to himself if no one else.

On Day 2 in Iowa, Mar. 9, Hickenlooper mingles with potential supporters at an event at Octopus, a bar in Cedar Falls. | Stephen Voss for Politico Magazine

The toilets were the easy part. Hickenlooper and his partners poured everything they had into the project, and did most of the work themselves. They bought wheat and grain to store in the basement, where they also kept much of the equipment. They built two bars on the first floor and set up tables for the restaurant. They heaved more than 20 pool tables up to the second floor and named it Wynkoop Billiards, the biggest pool hall in the city. Now all they needed was customers.

“The Wynkoop was done on a shoestring, with family and friends as investors, and it was risky. The level of expertise you need to run a brewpub, it’s not running a fast-food concession,” says Patty Calhoun, the founding editor of Westword, the city’s acerbic alt-weekly, who worked in the neighborhood and became one of Hickenlooper’s regulars.

At the grand opening, a panicked Hickenlooper poured beers in solo cups for 25 cents each because the dishwashers couldn’t keep pace. Calhoun chuckled at the newcomer’s awkwardness. Yet as she and her colleagues got to know him over many late nights at the bar, they concluded he was just about the most colorful—and curious—character they’d ever met.

“He loved to gab late into the night, he loved talking to people, he loved learning about people. Whenever he heard about somebody’s job, he would say, ‘Wow! Maybe I should do that!’” she recalls. Hickenlooper so loved the late-night, booze-fueled arguments among his regulars—over music, sports, politics—that in those pre-Google days, he proposed hanging a dictionary by a string from the ceiling, dangling over the bar, so that they could resolve the conflicts.

The good times and strange circumstances were too many to number: How he offered a $5,000 “bounty” for anyone who could find him a wife and wound up discussing the contest on The Phil Donahue Show; how after celebrating one Wynkoop anniversary with a pig roast he proposed a “running of the pigs” in the alley behind the restaurant, only to end the practice in the face of protests from PETA. Sometimes he had too much fun: The year after the bar opened, Hickenlooper was arrested for drunk driving, after which he introduced a designated-driver program at the Wynkoop.

Traveling the premises with Hickenlooper today, hearing the bartenders talk of “the brewery that brewed a neighborhood,” it’s tempting to think of him as a visionary. The Wynkoop is visually stunning and commercially vibrant, spilling over with customers on a Tuesday afternoon. The surrounding area is every bit as impressive, a snapshot of 21st-century urban dynamism. But Hickenlooper is quite modest about his achievement, because in reality, the success of the Wynkoop—and of its ecosystem—was the result of good sense and great fortune.

Hickenlooper struggled mightily in the first year to turn a profit. Friends worried that the bar would go under. Eventually, he took the dramatic step of approaching the handful of restaurant and bar owners in the neighborhood and suggesting they join forces with a common purpose. It was an uneasy conversation to have; Hickenlooper argued that unless more people started coming to LoDo, they would all go out of business before long. Persuading his competitors to pool their resources to buy newspaper ads and bar supplies in bulk, the establishments soon began to thrive, with good publicity begetting steadier business, a cycle that perpetuated until LoDo, in a few years’ time, became the talk of Denver. In 1991, Hickenlooper and his partners purchased the building outright for $11 per square foot—a steal—and set about enhancing the restaurant’s operations and building condominiums on the top three floors. It was a triumphant—and dicey—expansion.

Enter the great fortune. Around that very time, Major League Baseball was awarding a franchise to Colorado with a promise from Denver to construct a glitzy stadium, and city officials were debating its exact location. The sudden revitalization of LoDo, on top of its still-inexpensive real estate, made it a natural candidate. But Hickenlooper—to the astonishment of his peers—was adamantly opposed. They were working organically to build up the neighborhood, Hickenlooper argued, and didn’t want a corporate takeover of the area, not to mention the drunks and general unruliness that can accompany professional sports venues.

“Luckily,” he laughs, “nobody listened to me.”

“From the Wynkoop to the White House” reads a chalk board, top left, at Hickenlooper’s campaign stop at the Octopus bar, alluding to the candidate’s Denver brewpub that he started many years ago which had set into motion the chain of events that led him to politics. Top right, Hickenlooper speaks with Democratic organizer Timothy Klinghammer at the same event, and, bottom, Hickenlooper campaigns at Quarter Barrel Brewery and Arcade in Cedar Rapids that same day. | Stephen Voss for Politico Magazine

In 1995, Coors Field opened just down the street from the Wynkoop. It was a winning lottery ticket: Sales shot up more than 50 percent when baseball season began, and the demand for his new condos went through the roof. The LoDo neighborhood was no longer a punchy underdog; it was the trendiest part of one of America’s fastest-growing cities. And it was making Hickenlooper rich. Before long, he made plans to expand into other cities. He would use the same model, buying cheap, dilapidated buildings in ignored sections of second-tier cities, hopeful that a successful business venture could help spark urban renewal—and profits. There were failures along the way, but also plenty of successes. In total, Hickenlooper opened 14 brewpubs nationwide.

Still, the Wynkoop is his baby. He no longer owns the business—having placed his stake in a blind trust while serving as mayor, he was crestfallen to learn it had been sold off—yet he’s still treated like royalty in the building. He breezes in and out of different rooms, calling out to employees, pointing out where things used to be and showing me the finer points of the brewing process. When he was governor, one of the bartenders tells me, Hickenlooper would arrive unannounced, sample the new selections, then disappear into the basement and drag a keg of beer up the steps himself, muscling it into a waiting SUV, with the understanding that it would be placed on his running tab with the owners. (He kept a kegerator in the governor’s mansion.)

Watching him roam the restaurant, listening to his yarns, it’s easy to envision him behind the bar, holding court with customers late into the night, telling old tales and picking up new ones, comfortable in his skin and at peace in the community he created. It was “a killer life,” he says, one that he could not imagine changing.

And then, he got suckered into politics.

He wants to tell me about it. But first, he needs to show off the kitchen. Barging through the double doors, winding our way back to a prep area next to some walk-in refrigerators, he explains how everything here is made from scratch. Glancing around at the cast of Hispanic women chopping vegetables—some of whom clearly do not recognize him and are startled by our sudden presence—Hickenlooper waves his arm, announcing grandly, “These are the geniuses!” With their stares unabated, Hickenlooper tries their tongue: “Geniosos! Geniosos!”

They smile politely, and he reverts to English, pointing to his head. “Geniuses!”

They smile some more, and we head back for the double doors. “So much for my Spanish,” he mutters to no one in particular.



***

The guest of honor is running late.

It’s an icy Saturday afternoon in Dubuque, Iowa, the second day of Hickenlooper’s swing through the state, and a crowd of some 50 local Democrats has crammed inside the home of Jack Wertzberger. A prominent local activist, Wertzberger is known to open his home to any visiting Democratic candidate so that voters can meet and question them in an intimate setting. The snow is beginning to drift outside and more than a few people are wondering where this particular presidential hopeful is.

Suddenly, before anyone knows it—before anyone notices him enter the house, or snake through the clogged foyer—Hickenlooper is seated at the piano in the living room, banging out show tunes and tossing his head from side to side like a poor man’s Elton John. Surprised, then delighted, some in the room start clapping along. “I never get a chance to play the piano,” he tells me. “You know, nobody thinks a politician can do anything except be a politician. Most of them have wanted to be a politician their whole life and they don’t have any hobbies.”

These twin instincts—a love of spontaneity, a loathing of “politicians,” a title he hisses despite having held elected office for 16 years—explain how he ended up playing piano in Dubuque.

Being mayor was never an ambition. Really, he insists, it was never even a consideration. But Denver at the turn of the century was a city overdue for transition, a new-money metropolis whose potential was being drowned in red ink and depleted by job losses to tech-heavy competitors out west. Hickenlooper’s first taste of politics had come in 1999, when he led the opposition to a corporate sponsorship of the Denver Broncos’ new football stadium, arguing that the iconic “Mile High” moniker from the old stadium should be preserved. (A compromise was reached, pairing “Mile High” with a corporate sponsorship.) Three years later, when the incumbent announced he would not seek a fourth term in City Hall, Hickenlooper thought nothing of it.

Prodded by friends to consider running, he laughed, then winced, then demurred. But soon the idea began growing on him. In the decade-plus since he’d opened the Wynkoop, Hickenlooper had become a fixture on the civic scene—joining local boards, catering charity events, sponsoring various functions. This made Hickenlooper a player, an influencer, in a city without any imposing blue-blood establishment. It also exposed Hickenlooper to the inner-workings of a political class he found unresponsive to the needs of the city.

“I'm not the typical little guy who makes it big,” he told the New York Times in 2003. “In the process of building a business, I’ve been involved with the community and I’ve never shied away from speaking up when politicians didn’t do so.”

Distressed at the prospect of leaving his “killer life” behind, Hickenlooper took 12 weeks of vacation to make his decision. He traveled the world with friends, eating and drinking in exotic locales and pondering a life in politics. Few of them thought he would change careers. He doubted it, too. And then, without much of a warning, he jumped in with his typical spontaneity—no staff, no plan and no expectations. “I was the last person to get into that race,” he recalls. “Everyone told me I was six months too late.”

It was a few weeks before his 50th birthday, and Hickenlooper was running the first campaign of his life.

Alan Salazar, a veteran Democratic strategist and then-chief of staff to Rep. Mark Udall, doubled over in laughter at the news. Salazar, who was backing the favorite in the race—a young, Hispanic, “Hollywood handsome” city auditor who “looked the part and knew city issues backward and forwards”—had met Hickenlooper just once. It was at the Wynkoop, a few years earlier, when a mutual friend introduced them. “He reached out in an ungainly way to shake my hand, and I noticed the elbow of this green suit he was wearing was fraying. He had glasses on, he had this goofy, cowlick haircut, and just looked kind of geeky and nerdy,” Salazar recalls. “So when I heard he was running for mayor, I just laughed and laughed: ‘Never gonna happen.’”

But Hickenlooper was relentless. For a first-time candidate, he demonstrated not just an uncanny ability to connect with people, but an intuitive understanding of their anxieties. (As proven by John Boehner and Alexandria Ocasio-Cortez, tending bar makes ideal training for future politicians.) Sensing the disquiet about Denver’s economic downturn, with office buildings around the city emptying out in a manner reminiscent of how LoDo looked two decades earlier, Hickenlooper built his candidacy around the promise of attracting business to the city. He ruled out tax hikes, opposed a ban on smoking in public places and even vowed to lower the cost of parking meters, an issue that seemed trivial until Hickenlooper won widespread acclaim for a television ad in which he strolled around downtown filling the meters with coins.

He won both the primary and general elections in comfortable fashion, marking a major disruption of Colorado’s party-driven political scene. The new mayor governed as uniquely as he had campaigned, making peace with suburbs that had long been at war with the city and forging alliances with Republicans in the pursuit of major economic development initiatives. Less than two years into his tenure, TIME called him one of America’s five best big-city mayors, noting how he “inherited a $70 million budget deficit, the worst in city history” and “eliminated the shortfall without major service cuts or layoffs, convincing city employees that they should accept less pay and instituting mandatory leave days.” More impressive, Hickenlooper secured bipartisan support for a series of tax hikes to fund various quality-of-life initiatives, the crown jewel of which was a nearly-$5 billion mass-transit project.

At the home, top, of prominent local Democratic activist Jack Wertzberger in Dubuque, Iowa, Hickenlooper surprises the crowd by finding the piano before anyone notices him enter and playing showtunes, bottom. | Stephen Voss for Politico Magazine

It was all rather confounding to the political professionals, watching as the nomadic newcomer ran circles around the city’s power brokers and rang up approval ratings in the 80s. “As far as real-life political fairy tales go, it was just about impossible to trump Mayor Hickenlooper,” read a 2012 article in Denver’s 5280 magazine. “He was a new kind of natural, one of those unicorn-rare, truly apolitical politicians that career politicos so often and so fraudulently claim to be.”

After winning his reelection bid with nearly 90 percent of the vote, the clamoring quickly began for Hickenlooper to run for governor in 2010. This time, he was less resistant to the entreaties. Hickenlooper’s taste for his adventure—“his endless curiosity, where he’s always trying things on for size, always continuing to grow,” as Calhoun says—was only growing in his mid-50s. He had become a father, took up the banjo and welcomed the challenge of running for higher office.

His first hire was Salazar, whom Hickenlooper named campaign chairman and chief strategist. With the intensifying recession and tea party wave crushing Democrats nationwide, Salazar was convinced that Hickenlooper was the party’s only hope to hold the governorship. He did, winning convincingly in a year that saw Republicans flip 12 governor’s mansions nationwide. Hickenlooper got some help from the GOP, whose badly flawed nominee was further weakened by former GOP congressman Tom Tancredo’s candidacy for the Constitution Party. (“One of John’s former girlfriends used to say that he stepped in lucky shit,” Calhoun laughs. “The timing has always been great to him.”) Even so, Hickenlooper won the race easily.

The job itself proved to be far tougher. In Hickenlooper’s first term, Colorado suffered a wave of unremitting wildfires, including three of the four most destructive in the state’s history, destroying more than a thousand homes, causing millions of dollars in property damage and claiming the lives of numerous citizens. Then, in 2012, a dozen people were killed and 70 injured when a shooter opened fire at an Aurora movie theatre. Finally, according to the Denver Post: “When the governor learned he would have to undergo a hip replacement, … he chose a week in September with no record of catastrophe.” Just after his surgery, “a 100-year flood hit northern Colorado. Nine people died, and the floods destroyed 1,852 homes and caused $4 billion in damage. On crutches, Hickenlooper visited all 22 counties that had been submerged.”

The Post added, “Between fallen soldiers, natural disasters and gun violence, Hickenlooper would attend more than 50 funerals during his first term.”

“We had this string of tragedies, and he had to identify how to be a leader in communities that were new to him,” says Tami Door, CEO of the Denver Downtown Partnership. “I think it was all about his empathy—he really relates to people as a human being, and they relate to him. But he was also able to make things happen. He delivered. These were policy issues as much as deeply human issues, and there was nowhere to hide from them.”

The well-documented détente Hickenlooper brokered between big energy and the environmental lobby resulted in an unprecedented methane-regulation policy that served as a blueprint for California and other states. His signing of some of the strictest gun control laws, including universal background checks for all gun purchases and a ban on high-capacity magazines, made him an enemy of the National Rifle Association. Meanwhile, with the Affordable Care Act under constant attack from Republicans in Congress, Hickenlooper strengthened his state-based exchange, leading to a nearly 95 percent coverage rate in Colorado. He also backed civil unions for same-sex couples well before marriage was a mainstream position in the Democratic Party.

One might think that Hickenlooper winning a second term in 2014, another terrible year for Democrats, would have vaulted him to the top of every vice-presidential short list in 2016. But the Colorado governor, despite his many successes, was never a progressive darling—a fact that does not escape him as he now seeks the presidency.

Hickenlooper’s cozy relationship with the Chamber of Commerce crowd, and his mass slashing of state regulations, is sure to come under scrutiny from the left. So too will his initial objections to the legalization of recreational marijuana, a stance that Hickenlooper eventually softened on, acknowledging the rapid swing in public opinion and the encouraging early returns from Colorado’s pot experiment. Ironically, for a scientist-politician most proud of his deal to protect the environment, his pragmatism makes him most vulnerable on that very issue: Given the urgency surrounding climate change for the Democratic base, his support for fracking—and his opposition to ballot measures that would have banned the construction of oil wells in certain locations—will almost certainly be used against him.

Hickenlooper is a cool customer, a people-pleaser skilled at masking his annoyance and avoiding insults. (He once showered fully clothed in a campaign as to demonstrate his distaste for negative campaigning.) But the questions about his environmental bona fides clearly irk him. At the brewery in Des Moines, when an environmentalist challenged him as to why climate change wasn’t his top priority—“like Jay Inslee,” a rival candidate—it was all Hickenlooper could do to keep from rolling his eyes. “Because bringing people together is my top priority,” he said, insisting that only through bipartisan consensus can meaningful progress be made. At the Dubuque house party, after fielding another inquiry about climate change, Hickenlooper gives a blunt response that, translated, amounts to: I’ve actually effected realistic change, while these other people fantasize about ideas that are never going to become law.

Or, as he tells me inside his Infiniti SUV a few minutes later, as his driver navigates eastward, “We’ve been able to deliver real progressive results in some very difficult circumstances—not just talk. I’m not just a dreamer, but a doer.”



***

It’s been a few weeks since we toured the Wynkoop in Denver, and as we talk in the middle row of his campaign’s rented car, I can’t help but ask about the face blindness—a seemingly debilitating condition for an aspiring president.

It was only five or six years ago, Hickenlooper says, that he came to realize his condition. “I bought into the thing that, as my mother said, my siblings said, my girlfriends, they just said, ‘You don’t pay attention,’” he laughs. Only when he read an article by the late neurologist Oliver Sacks, who also suffered from the cognitive disorder, did Hickenlooper make sense of his own struggle.

So, I ask, did you recognize me today?

“No,” he says, shaking his head. Then he adds, “I did, because I knew you would be here. So I didn’t recognize you, but then as we were walking out, then I figured out who you were.”

Hickenlooper says if he sees a person often enough, “four or five times per month, I begin to kind of get it.” Still, it’s difficult to overstate just how crippling this condition might be for someone who is about to spend the next 10 months—if not longer—working party activists and rope lines. In Iowa alone, there are 99 counties, which means 99 chairmen, 99 vice chairmen and a thousand other local Democratic officials and activists who want to be flattered, who want to be lavished with attention, who want to be remembered, before they commit to caucusing for someone. Bill Clinton used to keep note cards with personal information about a person’s family and interests to dazzle them with a personal touch on the chance they met a second time; Hickenlooper can’t remember meeting someone unless he sees them once a week.

He laughs off my concerns, describing how running a restaurant with his impairment makes running for public office seem like a breeze. He also explains his system: His top staffer in each state will have to brief him in detail before every meeting, every phone call, every house party, about who he’ll be talking with and whether he’s talked with them before.

At the offices of small businessman Jim Davis in Charles City, Iowa, Davis, bottom, introduces the Colorado businessman who, while running for the Democratic nomination for president, calls himself a “fiscal conservative.” | Stephen Voss for Politico Magazine

It’s a daunting challenge, but then again, Hickenlooper has lots of those to worry about. Chief among them is selling his brand—that of an “extreme moderate,” as he boasts of being called—to a party base that wants sweeping progressive change. For Hickenlooper, while careful not to sound as though he’s on the attack, this boils down to a simple distinction. Whereas most of his rivals are lawyers by trade, he is a scientist, the first geologist ever elected governor in the U.S. (And, he adds for good measure, the first brewmaster elected governor since Samuel Adams.) His point is that while lawyer-politicians are trained to argue, scientists are taught to deliberate.

“I’m sure you’ve seen many of the same stories I did. ‘What chance does he have?’ And, ‘He doesn’t take a strong enough position on this or that,’” Hickenlooper says, rolling his eyes. “Which is sort of how science works, right? You don’t jump to snap judgments. You try to make sure you get all the facts, and think it through, then make better decisions.”

The fact is, whether it’s the way Hickenlooper reaches certain decisions or the decisions themselves, his centrist instincts place him out of today’s Democratic mainstream.

On health care, he is not simply defiantly opposed to Medicare for All—a single-payer health care system that would eliminate private insurance—but seems somewhat bemused by it. Hickenlooper says that with research showing more than 100 million Americans satisfied with their current, employer-provided insurance plans, it would “make no sense” to force them into a new program that costs trillions of dollars to implement.

On immigration, he blames bad actors in both parties for scuttling compromises. He also says he wouldn’t allow the question of citizenship for the undocumented population—even those brought here as minors—to thwart a potential comprehensive solution. Hickenlooper adds that he’s struck by how many young people—and the young DREAMer at this last event was one of them—come up and say, “Give me 10 years, a visa, and then maybe another 10 years on the visa, and I will figure out the citizenship thing. We don’t want that to be a holdup.”

When it comes to matters of spending and deficits, Hickenlooper calls himself “a fiscal conservative.” He rejects the trendy notion among some liberals that the national debt is a meaningless statistic, and even harkens back to borrow from the old Bill Clinton playbook. “I don’t think the government needs to be bigger. I think the government’s got to work, and people have got to believe in government, and I think that’s part of the problem,” he says. “I think what a lot of Americans want is better government, not bigger government.”

Even when Hickenlooper gets worked up, warning me that he’s about to “get raw” with his criticisms of Trump, he finds a way to dial back. “What word is most synonymous for ‘fascist’? It’s ‘bully,’” he says. “And dividing people has been a tool that bullies have used, but also dictators have used, for years.”

It’s a bit jarring, the sharpest remark I’ve heard him make. Is he saying that the president of the United States has fascist tendencies? “No, I’m not going to say that,” Hickenlooper says quickly. “But I’m going to say he has made an art of dividing the American people.”

This restraint could be thought as Hickenlooper’s greatest appeal—and also as his most conspicuous weakness. His stump speech is heavy on positive vibes but light on the specifics that add up to an overarching vision. “Bringing people together” might resonate with a certain chunk of the Democratic electorate, especially since he has a record that backs up his rhetoric. Yet a large and seemingly growing segment of the population believes America can’t be brought back together, that its partisan wounds are too deep to heal. For these voters, paeans to unity are unwelcome bordering on offensive.

Deep down, Hickenlooper seems to know this. He grimaces when I ask a question he surely saw coming: Would he consider choosing John Kasich, the former Republican governor of Ohio with whom he was once rumored to be considering a “unity ticket,” as his running mate?

“I think beating Donald Trump is absolutely essential. And I think at this moment and in this time, it would be very hard to beat Donald Trump if you had a Republican on the ticket,” he says, a pained expression exaggerating the creases in his brow. “There are so many Democrats so angry at the Republicans that they would feel betrayed.”

Cruising southeast toward Clinton, Iowa, parallel to the icy waters of the Mississippi River, Hickenlooper adds, almost apologetically, “You know, someday this country will get to that point. But at this moment in time I just don’t see it.”



***

Hickenlooper is about to commence his fourth campaign event of the day, this one inside a coffee shop in Clinton, and he’s got one more stop in Cedar Rapids that evening before hopping on a plane and flying to Austin, Texas, for the annual South by Southwest festival. It’s a long, grueling start to what he can only hope will be a long, grueling campaign. Hickenlooper says he scored “off the scale” for extroversion on the Myers-Briggs personality test—literally, his score did not register—and can think of nothing better than spending 16-hour days meeting new people. “I’m frustrated I have to wait a whole hour before I can talk to somebody else,” he tells me, between stops.

By the time he gets to his second to last campaign stop in his two-day swing through Iowa on Mar. 8 and 9, Hickenlooper is fading, and he admits he’ll have to make some lifestyle adjustments to get used to the pace of a presidential campaign. | Stephen Voss for Politico Magazine

That said, Hickenlooper knows lifestyle adjustments will need to be made. He will need more sleep. He will ask his campaign for eight hours to himself, from the time they reach the hotel at night until the time they depart in the morning. Most significant, he will cut back considerably on his beer intake—the biggest sacrifice of all. “I’m not going to be able to have a drink with dinner every night, because oftentimes I’ve got to go do a TV interview, I’ve got to go to a house,” he says. “It’s hard. I’ve got to be as sharp as I can be.”

Indeed, although it’s only day three of his campaign, and despite his love of life on the trail, Hickenlooper is fading at the stop in Clinton. His answers to several questions are particularly circuitous. His stump speech is rushed and robotic. His “Giddyup” line falls totally flat. This should be Hickenlooper’s kind of crowd, working-class Democrats in a region that was long ruled by Blue Dogs. But it’s not his best performance, and based on the vibe in the java house, he’s not winning many converts.

“He’s not at the top of my list,” says Jean Pardee, who served nearly two decades as the chairwoman of the Clinton County Democratic Party and has been a member of the state central committee for almost 50 years. “I think he comes across as appealing, but you can’t get too wonky with an audience.” Pardee says Hickenlooper’s first answer, to a question about getting tough on China, was meandering and “a little thin.”

Then, unprompted, Pardee raises another concern: Hickenlooper’s recent appearance on MSNBC’s Morning Joe, during which he refused—despite several opportunities—to identify as a capitalist.

Hickenlooper tells me he doesn’t like “labels” of any kind, as if that rationalizes his reticence. Maybe it was just a bad moment. But the more plausible explanation is that even Hickenlooper is succumbing to the same pressures, consciously or subconsciously, that have forced most of the Democrats running for president further to the left than they’ve ever been before.

“He gets so excited, his brain goes so fast, it’s always been kind of a wild ride when you’re talking to him and he’s unplugged. Now he’s being more careful, and I understand why,” Calhoun says. “But it’s a shame. Because he is who he is, and he needs to embrace that.”