Today, Phillips is better prepared for a GQ photo shoot than campaigning, with puffer vest atop a sweater, jeans, and pristine Red Wing hiking boots. The ride is bumpy, the cabin reeks of exhaust, and the engine is so loud that Phillips practically has to shout to be heard.

The truck mostly garners stares, waves, and smiles. Every once in a while, the wannabe congressman gets a middle finger.

If successful, Phillips would be the first Democrat to represent the district since 1961. But call him a politician, and he’ll correct you. “I don’t aspire to be a politician. I aspire to be a representative,” he says.

Yet while he may be just an attempted politician at the moment, he’s well on his way to full-fledged membership. Phillips’ words tumble forth as if by script, replete with rehearsed anecdotes and policy points that seem straight from a consultant’s handbook on targeting moderate voters.

He describes himself as “fiscally responsible, socially inclusive.... I don’t want to go to Washington to fight. I want to go to Washington to collaborate and salute the best ideas in the Republican Party with the best progressive ideals that I represent.”

Brandon Werth

Getting him to pinpoint those ideals is another matter.

In a sense, his game plan is much like Paulsen’s, who’s known for playing the Minnesota Nice Moderate at home, yet voting as if he represents Alabama while in Washington.

What Phillips does have going for him are the twin angels of conventional politics: deep pockets and the schmoozing acumen to seduce. A smile, a laugh, and a sensitive nod have a way of blotting out the garbled message coming from his mouth. Phillips’ charm is his wild card.

The problem: So far, it seems to be his only card.

Phillips’ backstory is a publicist’s dream.

He was born to Artie Pfefer and his wife, DeeDee, in 1969. Six months later, Artie was killed in Vietnam. DeeDee eventually married Eddie Phillips, heir to the Phillips Distilling fortune, one of the country’s largest distributors of wines and spirits at the time.

The Phillipses were known for their philanthropy. In the 1940s, they helped fund construction of Mount Sinai Hospital, the first in Minneapolis to extend staff privileges to black and Jewish physicians. Eddie’s father, Jay, started one of the original profit-sharing plans for employees, and was a founder of the Courage Center and the Phillips Eye Institute. Young Dean’s step-grandmother was Abigail Van Buren of “Dear Abby” fame.

After graduating from Brown University in 1991, Dean worked for InMotion, an Edina company that made bicycle equipment and apparel. Two years later, he joined the family business—but under the condition that he train in every department and obtain an MBA.

During the week, Phillips worked on the production floor and drove to mom-and-pop liquor shops across Minnesota. On weekends, he took classes at the University of Minnesota. When he graduated in 2000, his present was the presidency of Phillips Distilling.

He would go on to serve as chairman of Talenti Gelato, another family investment. The company would blossom into one of the nation’s top brands in the ice cream market before it was sold to Unilever.

Phillips now owns the upscale coffeeshop Penny’s, with locations in downtown Minneapolis and Linden Hills. The latter is housed in an old auto mechanic’s space reimagined as industrial chic. It’s spare and free of art, save for one neon sign. Be it weekday or Saturday morning, it’s likely to be standing room only.

The menu boasts matcha lattes, scratch-made almond milk, and turtle crepes. But Phillips sees it as much more, an experiment to test the $15 minimum wage, an idea he doesn’t believe should be decreed by government.

Phillips’ desire to challenge Paulsen was stoked by the ongoing dumpster fire of the Trump administration, and Congressman Paulsen’s vote to kill Obamacare. But his experience in politics is limited to a college internship and writing checks. He’s hosted fundraisers for Minneapolis Mayor R.T. Rybak and Democratic presidential hopeful John Kerry. He also gave $30,800 to the Obama Victory Fund.

While his history may be short on governance, it’s exactly the kind of background that lends itself to jumpstarting a campaign. He’s already the prohibitive favorite for the Democratic nomination, having raised $800,000 from individual contributors and special backing of the national Democratic Congressional Committee, which believes he’s the man to finally take down Paulsen.

Phillips longs for a return to whistle-stop campaigns, where candidates show up and talk to constituents.

Phillips had his eye on Karin Einisman since they met in Sunday school as five-year-olds. Eight years later, he asked her out. She said no. Phillips nonetheless harbored a “mad crush” until they reunited after college. They married in 1995 and had two daughters.

Daughter Pia was diagnosed with Hodgkin’s Lymphoma when she was 13. (“The worst weekend of my life,” Phillips says.) With her best friend, Pia turned the experience into a nonprofit called Pab’s Packs, which distributes backpacks full of donated comfort items like stuffed animals, blankets, and journals to patients at children’s hospitals.

“When I see my daughter doing that...,” Phillips starts to say, but pauses when tears interfere.

Dean and Karin divorced in 2015. His current partner is 29-year-old Annalise Glick, a devastatingly pretty musician-turned-art-consultant from Bloomington. She’s the proprietor of AGG | Glick Gallery, a mish-mash gallery that also sells clothing and home goods with an emphasis on local makers. The aesthetic is akin to the Walker Art Center, albeit with more textiles. Its limited hours and unanswered phone suggest that Glick doesn’t spend much time there.

When asked if he’ll marry again, Phillips says, “Absolutely. I hope so. I celebrate marriage. A lot.” For now, however, “I’m married to the campaign.”

At the helm of that campaign is election finance reform. Phillips refuses to take money from PACs and lobbyists. This comes in stark contrast to Paulsen, who has evolved from a moderate state legislator to a virtual caricature of the corporate congressman, routinely voting against his district’s interests in favor of his benefactors. He voted for the recent Republican tax bill, despite its harsh treatment of residents in high-tax states like Minnesota. And Paulsen has been almost obsessive in his pursuit of lowering taxes for the hyper-profitable medical device industry, which sends him more money than it does any other member of Congress.

“I like to debate,” says Phillips, “but I do not like to antagonize.”

Over five terms in D.C., Paulsen has collected more than $7 million from various special interests. (He did not respond to repeated interview requests.)

Phillips has placed this ability to purchase a congressman at the center of his campaign.

“Whether you’re talking about tax policy or health care policy or gun violence reduction or opioid addiction programs, none of this will be accomplished as long as politicians are beholden to interests that have lots of money and lots of influence.”

Phillips longs for a return to whistle-stop campaigns, wishing more candidates would do what he’s about to do at the dog park: show up and talk to constituents.

“When we start losing that human interaction, I think a lot of people start feeling like they’re not heard and listened to,” he says. “Bernie Sanders and Donald Trump recognize the same underlying need of people, which is to be heard. I think Donald Trump was part of a wonderful strategy to make people believe he really cared about them. If you look at what he did versus what Hillary did—he had rallies, big rallies. Hillary Clinton spent, I think, way too much time in fine homes and country clubs raising money.”

The irony, of course, is that both Trump and Phillips are wealthy men who elbowed their way into politics as major donors. But while Trump is a tsunami of erratic bombast, Phillips is a cautious people-pleaser, careful to not offend. “I like to debate,” he says. “But I do not like to antagonize.”

Though he sees himself as a “velvet hammer,” it’s hard to imagine him coming down hard on, well, anything.

At the Plymouth dog park, he greets people near his truck, which has been outfitted with a window that allows him to serve coffee. One is Andrew Morrow, an Excelsior father of three high school-aged daughters who wears a U of M beanie with “FEMINIST” knitted on the front.

Morrow befriended Phillips at a parade in Plymouth. When he shared that his daughters are part of a government-minded student organization at Minnetonka High School, Phillips offered to speak to the group.

Morrow contrasts this with Paulsen’s visit to the school last fall. “My daughter came up to him and he happened to be in the lunch line serving lunch. She asked him a couple of questions and he just flat-out lied to her. She was crushed and said, ‘No, that’s not right,’ and it was sort of a ‘move along, move along, you’re in the lunch line’ kind of moment.”

Yet Morrow has a more personal motive for opposing Paulsen: a daughter with Type 1 diabetes. The congressman not only voted to kill Obamacare, possibly leaving tens of millions of people without insurance, but also backed a move to allow insurers to bar coverage for preexisting conditions.

This sentiment—that government is working against family values—is shared by a bundled-up woman. She’s a counselor at a high school where 35 percent of the students qualify for free or reduced lunch. There’s also a large Muslim population.

After Trump’s victory, she says, white students chanted about building walls.

Phillips’ history of addressing such behavior isn’t exactly reassuring. During his first town hall, Sarah Park Dahlen, a professor at St. Catherine University, asked how he’d handle white supremacy.

“I don’t think there is white supremacy,” he responded. “I don’t think there is such a thing. We are not supreme. Human beings are supreme.”

It was typical of Phillips. Even on softball questions like these, he tends to respond with words that sound pretty and enlightened, but carry little practical meaning.

“I was very unhappy with his answer,” Park Dahlen says later. But she also saw a deeper side of the candidate. In a subsequent exchange on Facebook, the professor recommended Phillips read A Good Time for the Truth and The First R: How Children Learn Race and Racism. He already had the former, sending her a photo of it on his desk.

“The last thing I want is for people to walk away from watching the [YouTube] video and think, ‘This woman of color was really mad at Dean Phillips,’” she says. “I was, but what I appreciated is that afterward he continued to engage with me multiple times. That makes me feel like he’s a candidate that I can get behind and support.”

At the same town hall, Phillips stumbled on the Walker Art Center’s “Scaffold” controversy, which erupted over artist Sam Durant’s installation depicting the Mankato gallows where 38 Dakota men were hung after the U.S.-Dakota War of 1862.

Phillips was on the Walker board at the time. “If there was ever an example of why this board needs to be more diverse, it’s for days like this,” he claims to have told fellow members after the issue flared.

Then again, it’s fair to ask why he didn’t notice the board’s makeup—or the explosion the installation would cause—before the Walker was besieged with protests.

Phillips is late. A half-dozen people at the Excelsior library fidget in their seats. Most appear over 50 years old.

Four campaign staffers are here, as is Sterling Silver, a GOP tracker whose job it is to film Phillips in the hopes that he’ll say something off-color.

Zach Rodvold, Phillips’ campaign manager, is on bouncer duty. He’s slender and pale, with a balding dome and a perpetually glum expression—not exactly intimidating. Rodvold urges Silver to leave the room on the premise that today’s event isn’t a speech. Filming would make people uncomfortable. They debate for a few minutes like toddlers arguing over a coveted toy before Sterling reluctantly takes a seat outside.

“Dean is so consistent that I’m not that concerned about him,” Rodvold says.

Clara Severson, a white-blond millennial and Phillips’ volunteer and engagement coordinator, says that Phillips must have run into traffic. A few minutes later, Caitlin Grady, an Anna Kendrick lookalike and Phillips’ scheduling and operations director, explains away her boss’ absence by calling the campaign truck “temperamental.”

When Phillips finally strides in 15 minutes late, he’s dressed posher than on previous occasions in a sports jacket atop his standard jeans and un-scuffed boots. It’s Halloween, and residents of this old-money town are lined up outside for the annual parade. Phillips runs back out to the truck and retrieves the same Halloween costume he’s worn since 1998: Winnie the Pooh.

He’s trying hard to be the everyman. He starts, as he always does, with his origin story, followed by his campaign finance reform spiel.

A woman asks about gun control, a term Phillips doesn’t favor. “My position is on gun violence,” he says. He wants it declared a “national health and public safety crisis.”

Since 1996, Congress has barred the Center for Disease Control and Prevention from investigating the issue, in deference to the National Rifle Association. But Phillips sticks to middle ground, calling only for more study and universal background checks.

His responses today are slick and short. During a previous conversation, he was wary of proposals to eliminate bump stocks, silencers, and make assault rifles illegal. He even made air quotes around the word “assault.”

Today, he’s making a concerted effort to be all things to all people. A woman asks about abortion. Phillips shows his burgeoning polish.

When asked a month before if he was pro-choice, he said, “Absolutely. 100 percent.” But he backtracked minutes later. “I’m pro-life. And I’m also pro-choice. And I don’t think they’re mutually exclusive. I think it’s really important to be both. And I celebrate both.”

At the library, he’s once again touting his support for a woman’s right to choose. He accentuates his commitment by mentioning the Planned Parenthood fundraiser he attended the night before. Bragging about galas is a recurring motif.

When someone asks about the environment, Phillips invokes his middle-ground credentials, name-checking former GOP Gov. Tim Pawlenty’s push for renewable energy, while frequently lauding Republicans for their good deeds.

Noticeably rare is for him to praise women in politics. Hillary Clinton frequently plays the punching bag, though he held a fundraiser in his home for her in 2015.

He also comes off as strangely enamored with the Trump campaign and its singular message: Make America Great Again. “If you looked at Hillary Clinton’s website back during the last campaign, it had I think 297 policy prescriptions, and Donald Trump focused on one,” Phillips says. “I’m focusing on truth and justice and American values.”

Yet it feels like a novitiate’s analysis. Trump’s support was concentrated among rural, low-education voters. Phillips is charged with winning the minds of the western Minneapolis suburbs, which are loaded with the highly educated. There’s an argument to be made that Trump’s simpleton approach will seem more insulting than ingratiating, especially among women who are increasingly prone to take flight from the Republican Party, and whom Phillips can’t win without.

Phillips has a lot to learn, but his inexperience doesn’t seem to dissuade his fans.

“He made a lot of good points,” said Bill Lester, a silver-haired Shorewood resident whose vote tends to bounce from Republican to Democrat to independent. “He didn’t get up there to promise a lot of different things. He just said, ‘Hey, I’m here to represent you. Here’s what I believe.’”

Larry Jacobs, a University of Minnesota political science professor, believes Phillips will need a lot more than that to win. He calls Paulsen “one of the most gifted politicians currently in office in Minnesota,” pointing to his last win over DFLer Terri Bonoff with 57 percent of the vote. This in a district Trump lost by 10 percent.

Bonoff, a state senator, was considered one of the better minds of the Minnesota Legislature. “If she lost, it’s not clear to me why Dean Phillips is better qualified in a professional political sense or has greater political gifts,” Jacobs says.

Yet Phillips clearly does have gifts. In a sense, he’s like a pop song: repetitive, irresistible, feel-good, but short on substance. Many a leader has been elected on a platform weaker than irresistible charm.

While Paulsen may be a gifted politician in the traditional sense, he also makes for an exquisite villain in the contemporary one. His voting record is nearly identical to the interests of his biggest donors. Whether it be health care or the Republican tax bill, he’s shown a unique willingness to vote against his constituents if the money’s right.

Phillips has his own red flags. He’s the rare Democrat who admits to watching Fox News without ironic intent. He’s a silver-spooner with no personal experience in the paycheck to paycheck—or no check at all—life. He believes in the “moral right” of health care, yet dragged his feet for a year before providing a plan to full-time employees at Penny’s.

And make no mistake: He’s very much a politician. He has an uncanny ability to make canned anecdotes feel like they’re being delivered for the first time. He’s young, handsome, and charismatic. In a vote on personality alone, Phillips is a shoo-in.

State GOP Chairman Jennifer Carnahan dismisses him as “an over-hyped challenger.” Maddie Anderson, a press secretary for the national GOP, considers him a mere opportunist. “He has no real convictions, no real reasons why he wants to run.”

Adam Jennings, a Democratic Tonka Bay councilman pursuing the same seat, also questions his sincerity: “I think he’s running Republican-lite and we’ve been down that road too many times,” he says. “I think he’s the wrong candidate for this race and I’m not sure he’s necessarily running for the right reasons.”

In the end, the race between Paulsen and Phillips may very well come down to the devil you know versus the devil you don’t.

“I’m not trying to be everything to everybody,” Phillips says. “But I am trying to be somebody for most of us, in the middle.”