Perhaps what most sets him apart from the large Democratic field is the way he invokes values like faith, freedom, and patriotism that have come to be seen as the province of conservatives. “American values ... are not values that belong to one party,” he tells a crowd in Ottumwa. ”They’re values that belong to all of us – but that I also believe point in a very progressive direction when we take them seriously.”

Last week, he made a swing through half a dozen Iowa counties that had voted in favor of Barack Obama, but flipped to support Donald Trump in 2016. Mr. Buttigieg, the gay Midwestern wunderkind, would like to woo those voters back.

A son of the heartland and a graduate of Harvard, Mayor Pete Buttigieg of South Bend, Indiana, combines a folksy manner with intellectual firepower that elicits chuckles and cheers. Since bursting out of the gate this spring with a flood of media attention after a town hall appearance went viral, he has lately been polling in the single digits. But he has been highly successful at fundraising, which means he has the resources to make a strong showing in the crucial Iowa caucuses.

Gary Kupferschmid managed to snag the autographs of five presidential candidates in just three hours at the Iowa State Fair this month, adding to a hefty collection that includes Jimmy Carter, George W. Bush, Barack Obama, Hillary Clinton, and Donald Trump – the last of whom got his vote in 2016.

Now Mr. Kupferschmid is back in his hometown, standing on the dimly lit porch of the Port of Burlington as the Mississippi River flows by, waiting for a signature from the latest candidate to roll through.

But Mayor Pete Buttigieg is hard to get to. He is mobbed everywhere he goes in Iowa. Supporters press in, standing almost nose to nose with him, waiting for their turn to exchange a few words.

“I’m so nervous. You’re such a rock star,” gushes one woman. A man sporting a BOOT EDGE EDGE T-shirt that doubles as a pronunciation guide urges the mild-mannered mayor from South Bend, Indiana, to “do a Kamala Harris” in the next debate, referring to the California senator’s more combative approach. “Stand out!”

In the middle of it all, a little girl looks up at the youngest of the presidential candidates and says: “I hope you get to be president.”

“I hope so, too,” he responds, bending down toward her on a swing through more than half a dozen mostly rural counties after an appearance at the Iowa State Fair last week. All but one of those counties share a common characteristic: They voted in favor of Mr. Obama, but flipped to support Mr. Trump in 2016. Mr. Buttigieg, the gay Midwestern wunderkind, would like to woo them back.

Christa Case Bryant/The Christian Science Monitor Gary Kupferschmid, who voted for Donald Trump in 2016, got Pete Buttigieg to sign his button in Burlington, Iowa. Mr. Buttigieg is trying to woo Trump voters in the southeastern part of the state.

“We lost an election in ’16 because, I believe, we didn’t hear that very clear message from rural people,” says Democrat Patty Judge, a former lieutenant governor and secretary of agriculture for Iowa. “They thought that Donald Trump was change, was an opportunity for them – of course that was not true. They are going again to be looking for that opportunity and change.”

She hasn’t endorsed a candidate yet, but calls Mr. Buttigieg’s new plan for rural America “very strong.” And indeed, he is positioning himself as a son of the heartland, who’s on a mission to reclaim quintessential American values like faith, freedom, and patriotism as not solely the province of the GOP. At the same time, he is deliberately redefining those values in progressive ways. He refers to Trump voters as “our friends,” and speaks of the pain of rural America and the importance of seeing it as part of the solution on everything from the economy to climate change.

Since bursting out of the gate this spring with a flood of media attention after a town hall appearance went viral, Mr. Buttigieg has lately been polling in the single digits. But he has been highly successful on the fundraising front, which means he has the resources to lay the groundwork for a strong showing in the crucial Iowa caucuses six months from now. His campaign sees southeastern Iowa as especially fertile territory, says senior communications advisor Lis Smith. They are hoping to convert Trump voters like Mr. Kupferschmid.

The message is essentially, “Look, Donald Trump talked a good game. He said he was going to go out there and fight for you, but he hasn’t,” says Ms. Smith, following the Buttigieg media mob at the state fair as he heads over to flip pork chops with the Iowa Pork Queen. “It’s not about saying that they’re complicit in a crime or that they’re horrible people for voting for him. It’s just saying, now is your chance and we will actually fight for you.”

‘Who is he?’

But first, he has to get on more people’s radar screens. Despite the intense cohort of fans who seem to follow him everywhere, plenty of Iowans still who have no idea who he is. As Mr. Buttigieg and his entourage stroll around the fairgrounds in Des Moines, they leave in their wake many puzzled expressions.

“Who is that?” asks one onlooker.

“Pete Buttigieg,” replies someone nearby.

“And who is he?” asks a third, looking confused.

“I have no clue who that is!” says a boy.

“No clue,” agrees a woman next to him.

“Go Trump!” yells someone else.

From the bowels of the beer tent, someone recognizes him, yelling, “I got your book!” One supporter offers him half a plastic cup of beer. (An aide says no thanks; it’s only mid-afternoon.) Another insists on handing him a limp chocolate chip cookie. (A staffer discreetly throws it in the next trash can.)

Pete Buttigieg campaign Harris Mayer of Iowa City is ecstatic after Democratic presidential candidate Pete Buttigieg agreed to ride the slide with him at the Iowa State Fair in Des Moines on Aug. 13, 2019.

Mr. Buttigieg, dressed in a white shirt and jeans, takes it all in stride, never seeming ruffled or impatient. No matter what the question – Antifa, Brexit, climate change, the Hong Kong protests, Israel’s annexation of the Golan Heights, tensions in Kashmir, or his favorite subject in grade school (English) – he delivers an articulate answer with almost machine-like precision.

After traipsing all over the fairgrounds, he honors a promise made to a mother who asked him during the Q&A of his soapbox talk, “Will you ride the slide with my son?” “Of course I’ll ride the slide with your son!” he told her. “I don’t know what it means, but I’ll do it.”

And he does, high-fiving the little boy at the bottom. Then, fortified by all manner of pork, he heads off to Trump country.

“Trump is not the answer”

Burlington, Iowa, has been dubbed the Backhoe Capital of the World, and when Shearer’s is making chocolate chip cookies, the whole city smells amazing. It boasts its own Minor League baseball team, the Burlington Bees, and was the hometown of conservationist Aldo Leopold and astronaut Jim Kelley. It features hilltop Victorian mansions that can be purchased for $225,000.

But shootings are up and the population is down – the lowest it’s been in nearly a century. Employers complain that they can’t find good help. The rate of kids on free and reduced-price lunches has risen from just a few percent to more than 50% in the past few decades.

Though Burlington itself narrowly supported Mrs. Clinton, the county as a whole went for Mr. Trump. Up the river in Muscatine, it’s a similar story. Mayor Diana Broderson, sitting in the front row of an outdoor house party waiting for Mr. Buttigieg to arrive, says she wants “someone that’s looking out for the common man.”

Last time around, some supporters of Sen. Bernie Sanders – upset that he had lost the nomination to Mrs. Clinton – backed Mr. Trump instead. “I’m hoping that everybody has learned that our party has to be united,” says Ms. Broderson. “A great number of people in our community agree that Trump is not the answer.”

Kelcey Brackett, the Democratic chairman in Muscatine County, says he believes some Trump voters could go for Senator Sanders if he became the Democratic nominee. Other candidates, such as Sens. Cory Booker of New Jersey and Amy Klobuchar of Minnesota, could also win them over by setting a tone of bipartisanship. “I do think that’s important,” says Mr. Brackett, adding that there is also high enthusiasm for Mr. Buttigieg, who drew 225 people to the Muscatine house party on a weekday afternoon. “Otherwise the pendulum is just going to swing harder.”

In the lush backyard, Mr. Buttigieg is introduced as being, among other things, Maltese-American, left-handed, and a didgeridoo player. As at nearly every campaign stop, he receives a standing ovation before he even opens his mouth. A Harvard graduate and Rhodes scholar, “Mayor Pete” combines intellectual firepower with a folksy manner that elicits chuckles and cheers over even the driest topics.

“Basically, I want to Marie Kondo the bureaucratic process,” he says, referring to the bestselling Japanese decluttering expert who has encouraged millions to empty their closets of anything that doesn’t “spark joy.”

Christa Case Bryant/The Christian Science Monitor Dick Fenton, a retired John Deere machinist, came out to see Pete Buttigieg for the third time when he swung through Oskaloosa, Iowa, on Aug. 15, 2019, as part of a swing aimed at wooing Trump voters. “It’s going to be a rough row to hoe,” says Mr. Fenton, who moved to Iowa with his wife, Nancy, in the 1960s. “We grew up with Trump in New York and these people out here don’t know the half of it.”

Tongue in cheek, he describes his own memoir, “Shortest Way Home,” featuring “a daring young mayor who has a vision for the future of his community.” “It’s sorta how we’re paying off the wedding bill, so I’d be very grateful if you’d pick one up,” says Mr. Buttigieg, who married his husband last summer, and carries household student debt in the six figures. Forbes recently ranked him as the poorest presidential candidate, with a net worth of $100,000. But he has 23 billionaires backing his campaign, the most of any candidate. He has 60 full-time staffers in Iowa.

Campaign finance is “one of my favorites,” he says in response to a question, boiling the issue down to a simple equation: It’s not a democracy, he says, if dollars can outvote people. If Citizens United, the landmark 2010 Supreme Court decision, can’t be overturned, he adds, Congress should pass a constitutional amendment to “tune up our democracy.”

And speaking of democracy, he suggests counting up all the votes in a presidential election and letting the person with the most win. With such seductive logic, he doesn’t need to even mention the Electoral College or get into a messy debate over how and why the framers of the Constitution sought to prevent America from devolving into a tyranny of the majority. Everyone is already cheering.

Reclaiming – and redefining – American values

But perhaps what most sets Mr. Buttigieg apart from the large Democratic field is the way he invokes values that have come to be seen as the province of conservatives.

“I believe in American values that are not values that belong to one party – they’re values that belong to all of us, but that I also believe point in a very progressive direction when we take them seriously,” he tells a crowd in Ottumwa.

Take liberty, he says. It’s not just about freedom from regulations or onerous taxes. It’s about freedom to choose how to live – freedom for women to choose (one of his biggest applause lines), to get quality health care, or to marry whomever you want, regardless of what a county clerk thinks.

He and his supporters know such positions can be a hard sell in Iowa, where religious conservatives hold significant sway. “When I enthuse about you, people say, ‘America isn’t ready to elect a gay man president,’” a man tells Mr. Buttigieg at a campaign stop. Ireland has a gay prime minister and South Bend seems to have gotten over it, he continues. How can I convince them?

Mr. Buttigieg responds by sharing his own decision to come out after serving as a Navy Reserves intelligence officer in Afghanistan and returning to his job as mayor. He won reelection several months later with 80% of the vote.

“God does not belong to a political party,” he is fond of saying, adding that the Bible shouldn’t be used as a cudgel to tell people they don’t belong. He cites Scripture about feeding the hungry and caring for the stranger, and accuses the Trump administration of violating such tenets. He hopes, he tells the crowd in Muscatine, to make it “OK for those who are guided by faith to know that they don’t have to be pushed into the arms of the religious right – whose latest political decisions betray not only our values but also their own.”

And what about those whose deeply held convictions – religious or otherwise – do differ from his? He would like to persuade them, he says, but acknowledges that, “I won’t convince everybody, and that’s OK.” He adds, however, “that people who think a lot about freedom – conservatives and libertarians – should pause at a moment like this ... and ask if this isn’t a chance for resetting the entire spectrum in a way that will make Americans better off.”

Back in Burlington, as the last of some 500 attendees trickle out, someone with the Buttigieg campaign approaches Mr. Kupferschmid to return the baseball he had hoped Mayor Pete would sign.

“Hi Gary, I apologize profusely,” says the young man. “That’s OK, it’s better than Kamala Harris,” says Mr. Kupferschmid, who at least got his “Pete Buttigieg for President” button signed. “And he seems more genuine.”

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He says, though, that with a lot of his money in the stock market, he’ll probably vote for Mr. Trump again next year if it keeps doing well. But he implies that calculus could still change.

As he ambles into the warm summer night, he peers into a trash can and pulls out a Pete sign.