On a cold Saturday night in November, Pete Buttigieg leaned into his Midwestern roots. The South Bend mayor and Democratic presidential candidate was on the first leg of a tour of northern Iowa. In Decorah, a 7,594-person town, more than 1,000 people had squeezed into the high school gym for a town hall with the candidate. Addressing the people of Winneshiek County, a farming community that flipped from Barack Obama in 2012 to Donald Trump in 2016, he focused on agriculture. Answering a question about climate change, Buttigieg insisted that farmers have a critical role to play in staving off global warming, citing cover crops—beans or buckwheat, for example—grown to prevent weeds and enrich soil quality.

“I was super impressed with what he knew about farming,” Bridgette Hensley, 51, a psychologist, said after the town hall. Deb Tekippe, a 63-year-old retired nurse, agreed. “He’s one of us,” she said.

The next day, Buttigieg hurtled west aboard his blue and yellow campaign bus. As the vehicle passed cornfield after cornfield, he recited for reporters a portion of “When the Frost is on the Punkin,” the famous ode to harvest by the Hoosier poet James Whitcomb Riley. In Britt—population 1,973—Buttigieg swung by Mary Jo’s Hobo House, a breakfast joint, and asked farmers there about their crops. In Mason City, he toured an ethanol plant and mentioned that it reminded him of the one back in South Bend.

Patty Judge, a former Democratic lieutenant governor of Iowa who accompanied Buttigieg at some campaign stops, says his Midwestern-ness is playing well in the state. “He’s this down-to-earth, friendly person who people relate to, but he’s also an incredibly bright person with lots of ideas,” she says. “There’s a lot of agriculture in both Indiana and Iowa, working folks in both states, and he’s resonating here because of that.”

The dark-horse candidate is banking on his heartland bona fides to win the Iowa caucuses next month. Since August, Buttigieg has lavished attention on the state, underscoring his Hoosier background as much as any other part of his record. “You look at the Quad Cities, and they remind me a lot of home,” Buttigieg says. “You look at the rural counties, there are so many similarities to places like Marshall County or Starke County close to home in South Bend. I think the culture in particular—the expectation about how you engage other people regardless of what you believe about politics—is the same political culture that I came up in.”

The Iowa caucuses are still a few weeks away—a political eternity for a state that votes early but decides late. Still, in November, the candidate surged to first place in a Des Moines Register/CNN/Mediacom poll at 25 percent, ahead of Massachusetts Senator Elizabeth Warren (16 percent) and former Vice President Joe Biden (15 percent). At five events in December, he drew crowds of more than 1,000 at rallies in places such as Davenport, Mount Vernon and Corralville. At a November campaign event in Council Bluffs, he drew more than 2,000 people. He had gained 16 points since August. Buttigieg has 35 field offices here and more than 100 staffers on the ground—more than any other campaign at press time. If he could score an upset win in Iowa, it might change the trajectory of his entire campaign, which has been stuck in fourth in national polls. The white, Midwestern state should be friendly turf for a candidate who has struggled with African–American voters. That advantage cuts both ways, however. Buttigieg has bet a lot on Iowa. If he can’t win there, it seems unlikely he’ll win anywhere.

The modern-day Iowa caucuses have proven to be something of a political graveyard for Hoosier presidential hopefuls, candidates who once looked at the neighboring Midwestern state and saw it as fertile ground to till. In 1976, then-Senator Birch Bayh was the first Hoosier to participate in what had only four years earlier become the country’s first-in-the-nation electoral contest. Like Buttigieg, Bayh ran on electability and his Midwestern upbringing. A year before the caucuses, he had led early straw polls of the state. Bayh campaigned in a number of the state’s 99 counties, laying the groundwork for a bid to unseat Gerald Ford. But Jimmy Carter outmaneuvered him, all but living in Iowa. “No matter where I go in this state,” Bayh observed in December, a month before the caucuses, “that goddamned Jimmy Carter has been there four times before me.” When the final results came in, Carter won with 27.6 percent to Bayh’s 13.2 percent. The Hoosier finished seventh in Massachusetts not long after and dropped out. Iowa “was really a blow to me,” Bayh later told his biographer Robert Blaemire.

Then-Senator Richard Lugar also participated in the caucuses in 1996, but his patrician demeanor and professorial style never caught fire. He finished seventh with 4 percent, later dropping out after registering in the single digits in a number of states. And Evan Bayh campaigned in Iowa ahead of the 2008 election, but never formally announced a bid due to insufficient support.

“If he wins, I think that can erase a lot of doubts,” says one Democratic strategist of Buttigieg’s Iowa campaign.

For his part, Buttigieg has made Iowa part of his political origins story. Ahead of the 2008 caucuses, he took time away from his consulting gig at McKinsey & Company to go door-to-door for Obama in Iowa. There, in “one-stoplight towns,” Buttigieg recalls running into young men shipping out to serve. “And I began asking myself how it could be that whole communities in this part of the country, just like those in rural Indiana, seemed to be emptying out their youth into the armed services, while so few people I knew had served at all,” he wrote in his memoir, Shortest Way Home. Back home, Buttigieg enlisted in the Navy Reserves.

That experience is something Buttigieg has been eager to share in Iowa this winter. “The first time I came to this state was as a volunteer, to knock on doors for a presidential candidate—a young man with a funny name,” he told supporters at the Liberty and Justice dinner in Des Moines, where he packed an entire section of Wells Fargo Arena.

J.D. Scholten, an Iowa Democratic congressional candidate running against Republican Steve King, remembers marveling at the turnout. “One of the things I don’t think has been talked about enough is that he had people from all of Iowa’s 99 counties there,” he says. “You go to some of these counties that have not only been politically written off, but economically written off, and he has organizers there.”

Later in the Wells Fargo Arena speech, Buttigieg hit on his own outsider status. “I don’t go to work in an office in Washington, D.C.,” he said. “My office is about six hours that way down I-80, here in the Midwest. And out the window of that office, I see the outlines of our ethanol plant. Which is why I understand the measure of this president’s betrayal of American farmers, and I know how to talk about it.”

A little more than 100 days before the caucuses, Buttigieg held a town hall on the front lawn of Roosevelt High School in Des Moines. It was a frigid Saturday night, and the Iowa Hawkeyes football team was playing Penn State’s Nittany Lions on national television. But more than 700 voters braved the elements to hear the candidate deliver his short stump speech and answer questions.

One voter wanted to know: How would Buttigieg handle Trump on the debate stage? Given Trump’s penchant for insults, it was fair to wonder how a young guy with limited political experience would respond to the president’s barbs. “I grew up in Indiana,” Buttigieg responded. “I grew up dealing with bullies. I can deal with incoming [fire].” Buttigieg added that Trump would make it seem that Democrats were the party of Washington. “That’s why it might be a good idea to nominate somebody who was a mayor from the American Midwest who doesn’t work in Washington, but works on the ground to get things done.” The crowd roared.

Last January, it would have been hard to imagine a scene like that. Buttigieg trailed better-known candidates, polling near 0 percent in Iowa and nationally. Stops at coffee shops and pubs brought in a dozen or so voters. By April, when he officially announced his campaign, he was above 10 percent in some polls. Campaign stops drew a few hundred people.

Then last summer, Buttigieg began to invest heavily in Iowa. In August, he blanketed rural portions of the state with radio ads. Ahead of his ninth trip to the state in August, he announced a rural economy policy plan, which, among other things, included an $80 billion investment in broadband. He campaigned in seven southeast Iowa counties, six of which flipped from Obama to Trump in 2016.

“He’s very well organized there,” says Joe Trippi, a Democratic political strategist who has been involved in several Iowa caucuses dating back to the late Senator Ted Kennedy’s 1980 presidential campaign, including Howard Dean’s insurgent 2004 effort. “So can he win? If he wins, I think that can erase a lot of doubts.”

Trippi says that Iowa could play a similar role for Buttigieg that it did for Obama in 2008. “The whole thing holding Obama back at that point was, Is America ready for a black president? There were a lot of people who liked Obama but thought, I don’t think so. We’re not ready yet. When he won Iowa, it lifted many of those doubts. In a lot of ways, Pete [as the first gay president] could be like that.”

After Buttigieg’s town hall in Des Moines, supporters swarmed a Pete Mobile—what appeared to be a retrofitted ice cream truck from which volunteers passed out shirts and buttons—and staffers asked them to sign cards committing to caucus for Buttigieg. Asked whether he saw Iowa as a must-win state, he was unequivocal. “Iowa is critical,” Buttigieg said. “We’re investing, of course, in several early states, but one of the reasons I’m proud to have the most extensive operation in the state is because we’re going to need it. Look, Iowa is the place to settle the question of who can win an election.”

There are three tickets out of Iowa, conventional wisdom holds. According to Trippi, if Buttigieg fails to finish in the top three, it would ruin his chances—like those of other Hoosier presidential candidates who came before him.

Even so, Buttigieg has the resources to compete until at least Super Tuesday on March 3, having amassed $51 million in donations over the first three quarters of the year [Note: The Buttigieg campaign raised $76 million as of December 31, 2019]. He raised eyebrows in October when he hired Arielle Brandy as director of his Indiana campaign office. The move surprised observers because Indiana’s primary doesn’t happen until May 5. Among Indiana politicos, rumors swirled that should he perform poorly in Iowa, Buttigieg would parachute back into Indiana’s gubernatorial race. (The filing deadline is four days after the caucuses.) But with Buttigieg’s new national profile and popular Republican incumbent Eric Holcomb running in Indiana, the move wouldn’t make much sense.

“We’ve got our sights set on exactly one office,” Buttigieg says. “My goal is not to be holding some office. My goal is to offer what I have to really set the country in a different direction. Indiana needs a lot of changes too, but it’s very different than what I believe our country needs, and what I think I can offer in the presidential race.”

Scholten, the Iowa congressional candidate, says Buttigieg is in an enviable position entering the final sprint. “A lot of people question the jump from being a Midwest mayor to being president, but if you’re a campaign that started from scratch in January, and you’re where he is now, you have a chance to win,” he says.

If Buttigieg performs well in Iowa, he would face another friendly electorate in New Hampshire, where he leads the field with 25 percent of the vote, according to a recent Saint Anselm College Survey Center poll. He boasts 66 staffers and 13 offices in all 10 Granite State counties. Those wins would have to sustain him in two other early states with less favorable demographics: Nevada and South Carolina. Home to larger numbers of black and brown voters, with whom Buttigieg polls near 0 percent nationally, those states remain worrisome for his campaign. Nevertheless, Buttigieg is prepping for a longhaul run to what could be a contested convention, and began wooing superdelegates in July. He held a conference call with the powerful group, including Indianapolis’s own Cordelia Lewis-Burks, the black vice chairwoman of the Indiana Democratic Party who became the first Indiana superdelegate to back Obama in 2008. Lewis-Burks said positive things about Buttigieg on the July call, and introduced him warmly when he spoke to the Greater Indianapolis NAACP in October, but has yet to endorse.

If he finishes poorly in Iowa, some have speculated that a cabinet position might make sense. It’s not difficult to imagine Buttigieg at the Department of Veteran Affairs or even the State Department, for example. Asked on a recent bus tour if he would consider something like that, he said, “Sure, but I don’t think I should name them right now.”

The candidate could also stay outside D.C., running a think tank, foundation, or nonprofit that advances his policies. And then there are the vice president shortlists. Buttigieg has fashioned himself into an able attack dog of fellow Hoosier Vice President Mike Pence in a way that the eventual Democratic nominee might want to harness. But given Democrats’ remarks about balancing gender and race on the ticket, it’s unlikely he’ll pair with the leading contenders.

At least one thing is certain. On January 1, Buttigieg will become the unemployed former mayor of South Bend. He and his husband, Chasten, will enroll in Obamacare. “I think the [Shortest Way Home] book money will get us through the year, but it’s not like there’s a trust fund,” Buttigieg says. He added: “I’ve been saving up a little bit. Especially in the last kind of year or two, we realized, no matter what, there’s going to be a career change.”

Whatever happens next, Buttigieg will likely emerge from his 2020 bid as one of its biggest winners. Should he pursue his party’s nomination in 2024, he’ll be 42, roughly the age of Teddy Roosevelt, the youngest president to assume office, and still younger than John F. Kennedy, the youngest to be elected. In 2028, he’ll be just 46, about the age of Bill Clinton when he was elected to office. “You could argue that I’m a specialist in winning by losing,” Buttigieg said in an interview last year, referring to losing his state treasurer bid in 2010 (which preceded a winning run for South Bend mayor in 2012) and dropping out of his 2017 DNC chairman race (which he followed with his surprisingly strong presidential campaign this year).

But this fall and winter, Buttigieg seemed determined to win by winning. As 568 people gathered inside Iowa’s Waverly-Shell Rock Senior High School to hear Buttigieg on a Sunday afternoon, Cake’s “The Distance,” a reliable track on his campaign playlist, reverberated throughout the lunchroom.

He’s going the distance …