Mayor Pete Buttigieg illustration for Playboy

The Long Road to President Pete

South Bend's mayor has captivated millions. Can he sustain his momentum through debate season?

Nine days before Pete Buttigieg officially declared his bid for the White House, a woman approached the South Bend, Indiana mayor as he was waiting to board a flight to Manchester, New Hampshire, his third trip to the state since announcing his presidential exploratory committee in January. “She said, ‘Everyone’s coming up to you and saying hello,’ ” Buttigieg tells PLAYBOY. “And I said, ‘Well, yeah, it’s campaign season.’ She said, ‘Oh, what channel are you a reporter for?’ ”

He says that the encounter had been “a reminder that there are lots of people we need to reach—and also that we need to make sure this is a project of substance. Substance is key to outliving the flavor-of-the-month period.”

Buttigieg’s campaign raised an impressive $7 million in the first quarter of 2019, bolstered by a March town hall on CNN that resulted in more than 22,000 donations within 24 hours. Soon after, Buttigieg’s team was negotiating a televised town hall with Fox News, perhaps because that woman at the airport watches Fox News. Indeed, if she watched any other network—MSNBC at night, whoever airs Ellen during the day, CNN at any hour—she would have recognized the 37-year-old who has become the most unexpected and fascinating candidate in the 2020 contest.

This June, at the first Democratic primary debate in Miami, Buttigieg is expected to cross swords with as many as 19 competitors. Millions will tune in. Should he perform mildly well, anyone faintly interested in politics will know Mayor Pete’s last name—and, finally, how to pronounce its trio of syllables. (It’s boot-edge-edge.) Should he perform above average, he could wipe out half the field overnight. Buttigieg knows this is the advantage his rising-star status offers.

“The only point of doing this, especially coming from an under-dog position, is thinking that you’re going to introduce ideas that need to be there,” he says. “If we continue to perform, the debates could be a very good environment, because it will be just that many more people watching—hopefully people who will have the same response as people who tuned in earlier.”
The whispered problem is that two months before the debates, Buttigieg had yet to publish any official policy position on his website. He has instead spent his time doubling down on selling his campaign as grassroots, likely to temper the ascent that has propelled him to the near-front of the pack as the first millennial presidential candidate.

“You’ll continue to see us in every corner of the country, with an emphasis on the early states, because for a grassroots, underdog project like ours, that’s where you have the best chances at exceeding expectations,” he says. “The beautiful thing about this process is that a janitor in Iowa may have as much to offer a candidate as a senator from somewhere else.”

Buttigieg admits he’s been surprised by the “dizzying” pace of campaigning. While other candidates’ teams have launched strong operations in early voting states like Iowa, New Hampshire and South Carolina, his has remained shoestring. On his third visit to New Hampshire, for example, Buttigieg had only one paid staffer in the state, according to his campaign spokesperson, longtime Democratic strategist Lis Smith. It’s an endearing quality, but it’s not at all sustainable.

For now, “the most important thing is not to get caught up in your own coverage,” Buttigieg tells me during a tight 45-minute interview at a small café in Manchester—the largest city in the state, which hosts an early primary election. The night before, he sold out a trendy wine bar in Washington, D.C. where ticket prices ranged from $25 to $1,000. Here in Manchester, his campaign scrambled to move from a brewery to an art museum to accommodate a larger than expected turnout. At both of these appearances, the overwhelming show of support felt both worrisome and obvious. Buttigieg’s campaign seemed unprepared. He did not.
D.C. insiders know the road to winning the nomination will be a bloodbath.
After first-quarter fund-raising numbers ranked Buttigieg fourth behind Bernie Sanders, Kamala Harris and Beto O’Rourke—and a trio of polls ranked him third behind Joe Biden and Sanders—everyone simultaneously seemed to realize that the mayor of Indiana’s fourth-largest city was a legitimate candidate. But as Hillary Clinton can attest, poll results can be everything from misleading to flat-out incorrect.

“I don’t expect to learn that much from the polls in the next three months other than gathering validation of our name recognition,” he says. “We need to not be reactive but prospective. You’re not competing against any one candidate or combination of candidates. You’re competing against the house.”

The house includes a roster of well-qualified progressive senators who have been billed as the Democrats’ saviors since 2016 but who continue to blur in popularity and in and out of the media’s attention span. To say the Democrats’ united front is buckling would be an understatement. D.C. insiders know the road to winning the nomination will be a bloodbath. There is no clear front-runner. But that’s why the mayor has been able to stand out.

Much ink has been spilled about Buttigieg’s credentials, but let’s rehash it for posterity’s sake. He is the first openly gay Democrat to seek the White House but has no interest in selling himself as the LGBTQ candidate. He served in Afghanistan as a Navy Reserve intelligence officer but isn’t promoting himself as a hawk. He went to Harvard and became a Rhodes scholar, but he does not brag about either high honor in prepared remarks. His time at McKinsey, a top management consulting firm that draws the ire of progressives, is muted throughout his campaign.
Instead, he frequently reminds crowds that he is the mayor of a city in flyover country—a relatively scandal-free city that he describes as “the exact kind of geography the Democratic Party has struggled to be connected with. The South Bend story is such an important part of what I have to say about America. We’re not a wealthy, homogenous, tidy college town; we’re a diverse community with a complex industrial past. All of us have a mix of advantage and disadvantage in our story.”

A version of that line has been delivered not once, not twice, but ad nauseam. In Manchester it was repeated across two speeches—once to those inside the art museum and a second time to those stuck in the parking lot. Outside, when crowds began to grumble about having reserved useless tickets, one man loudly complained, “I’m curious what the point was having everyone sign up ahead of time. They want you on the mailing list is what it is. Great way to lose a voter.” Then Buttigieg popped up on a bench and started proselytizing—a jab at Beto O’Rourke. “I’ve heard that the way to ingratiate yourself to voters is to stand on things,” he quipped.

The next day, Buttigieg held an event in Concord, this time in a bookstore. It was a fraught venue that filled quickly, with the temperature rising to an uncomfortable level. Most in attendance couldn’t see the candidate. All they could hear was Buttigieg’s voice, noticeable for its youth. It wasn’t freighted with the gravelly rumble of Biden or Sanders. It carried none of the condescension of the establishment. It was his alone.
Buttigieg really came onto the national stage two years ago, in 2017, when he launched a bid for chair of the Democratic National Committee. The committee was wounded after the 2016 election fractured the party; Buttigieg thought he could put Humpty Dumpty together again. He ultimately dropped out of the race, but he did elevate himself as a national figure, and the political class studied up on his biography.

As he began to test the viability of his presidential ambition, New York media fixture Molly Jong-Fast hosted an intimate meet-and-greet that included BuzzFeed editor in chief Ben Smith and actor Zak Orth. She tells me the Midwestern mayor excites her because “he’s the opposite of Donald Trump in every aspect of his life and policy. He chose to fight in the war; Trump was a draft dodger. He is on the young side; Trump is on the old side. He learned Norwegian to read a book; Trump has never read a book. Religion is important to him; religion is not important to Trump.” According to Jong-Fast, the crowd of some 50 influentials was nothing short of blown away by the long-shot candidate’s résumé.
I have a lot of Parks and Rec moments.
As mayor of South Bend since 2012, Buttigieg has suffered only one major scandal, known around town as “the police tapes case.” Just before he took office, someone discovered that the South Bend police chief had been secretly recording internal phone calls. Some of the tapes allegedly caught white cops making racist remarks, including about the chief himself, who is black. The incident led Buttigieg to dismiss the chief, whom he describes in his book, 2019’s Shortest Way Home, as “well-liked,” while no action was taken against the white cops. At press time, the tapes had not been released, their fate tied up in state court. Buttigieg says he hasn’t heard the recordings. The lawsuits have cost South Bend taxpayers nearly $2 million, according to the South Bend Tribune.

Today Buttigieg presents that scandal as “an opportunity to explain how much I have learned the hard way about the importance of these issues…some of the questions of trust and the relationship between policing and communities and color.” Roughly a quarter of South Bend’s population is black.

During his first term he also launched an initiative to knock down or fix up 1,000 vacant houses in 1,000 days. Some locals claim the plan was blatant gentrification disguised as social good. Regina Williams-Preston, who lived in one of the affected neighborhoods, is now running for Buttigieg’s seat in City Hall. And in 2015, he remarked that “all lives matter,” though he has since apologized for that phrasing—which has been used to dismiss police brutality in black communities—claiming he didn’t understand it at the time.

Currently, none of these missteps have marred Buttigieg at the national level, but if he hopes to push past Trump in the general election, he’ll need to prove to communities of color he’s worth voting for. Although the number of eligible millennial voters is on track to nearly outnumber baby boomers for the first time in history, the 2016 election saw black turnout at the polls decrease for the first time in 20 years, according to the Pew Research Center. A proven utterance of “all lives matter”? Once Democrats start playing dirty, that line may prove to be gold for any opponent looking to own the black vote.
In Manchester, Buttigieg shakes a long line of hands and fields questions from supporters. A pair of teachers ask him to say hello to their classroom on their iPhones, and a former marine, followed by a young woman, asks if he’ll support student voting rights. Another man in line doesn’t want a photo; he uses his time to ask Buttigieg if he’ll consider doubling NASA’s budget. Somebody shakes his hand and tells him, “You’re my son’s age.”

After the museum empties, his team heads back to the brewery. Buttigieg looks like any politician after a relentless day of campaigning. His sleeves are scrunched up to his elbows, the lines on his face deeper than they were in the morning. Somebody hands him a root beer in a glass bottle, and I mention how the wide field of questions mirrors a scene from Parks and Recreation. Buttigieg nods. “I have a lot of Parks and Rec moments,” he says. 

While most of the candidates have singled out the president in their primary campaigns, Buttigieg asserts that Trump isn’t worth his energy, at least not yet. When asked about the president’s tendency to govern by signing stacks of executive orders, Buttigieg says he is “more interested in our agenda than his agenda.” He does have a simile for the president, though, saying 45 “almost became like a computer virus that breaks a computer by tying up all its processing power. That’s kind of what’s happening to the media with this president. I’m interested in changing the channel, and it will take a lot of discipline to do that. But,” he adds, “that’s the project, not just to punch back—which you have to do sometimes—but to get people thinking differently.” 
In a rare move for a presidential hopeful, Buttigieg has sparred openly with the vice president, who was governor of Indiana during Buttigieg’s first term as mayor and the early part of his second term. More important, Mike Pence was governor when Buttigieg came out to his constituents, in 2015. In his book, Buttigieg writes that “Pence’s fanaticism was hard to overlook, knowing how it had impacted me as a mayor—and as a person.” As governor, Pence signed the Religious Freedom Restoration Act, which allowed businesses to deny service to LGBTQ customers and was so disastrous that the state later hired a public relations firm to try to repair its image.

Pence is a useful villain for Buttigieg. He’s not any more well-liked than Trump (at press time, RealClearPolitics put Trump’s favorability at 42.6 percent; Pence’s hovers at 40 percent), and because of their at-odds history in Indiana, it’s hard to accuse Buttigieg of sketching an adversary to boost his credibility. At another event in early April, Buttigieg told a crowd, “That’s the thing I wish the Mike Pences of the world would understand: If you’ve got a problem with who I am, your problem is not with me; your quarrel, sir, is with my creator.” (Pence declined PLAYBOY’s request for comment.)

When I ask if he believes that legislating morality, and thus social conservatism, has become more prominent under the Trump administration, Buttigieg says, “I think the president made a fairly cynical decision to align himself with the evangelical right because that was necessary to bring him to power.”
Buttigieg has no choice but to play up his youth—he’s the same age as Ivanka Trump—but as his popularity has surged, he has had to work harder to articulate what he stands for lest he get boxed in as that guy who could be our “first young president.” He tells me he’s “most interested in launching legislation” and that “bad policies will need to be replaced. The question is what are we going to replace them with.” It’s a good question, and it feels strange to think Mayor Pete is running for president without answers.

His “concerns” (at press time, they had not been dictated as official positions) include promoting national service; investing in public education and increasing resources and compensation for public school teachers; reducing barriers to college education; overhauling the Pell Grant program; creating alternative pathways to success for young people who do not attend college; securing a woman’s right to choose; and “structural reform” to the U.S. government, including abolishing the electoral college and expanding the Supreme Court.

To suggest that any of these topics aren’t millennial at heart would be foolish. Despite his Ivy League pedigree, Buttigieg’s experiences are typical of his generation. He supports abolishing the electoral college, for example, because twice in his lifetime a Democratic candidate has won the popular vote but lost the general election. He grew up when text messaging took off and was in college on September 11, 2001. He had a MySpace account and attended Harvard when Mark Zuckerberg created Facebook. He met his husband, Chasten, who teaches junior high school theater in Indiana, on the dating app Hinge. His dogs, Buddy and Truman, are famous on Twitter.
He’s passionate without being eager, measured without seeming desperate to be liked.
Although he’s nearly a decade younger than the skateboarding, punk-rock Beto O’Rourke, Buttigieg’s youth feels different. He’s passionate without being eager, measured without seeming desperate to be liked. His political icons are neither surprising nor contentious. At the age of 18 he wrote an essay praising Sanders, then a congressman, which he closed with the following: “I have heard that no sensible young person today would want to give his or her life to public service. I can personally assure you this is untrue.”

When asked about his political influences, Buttigieg reaches back further. “The JFK presidency,” he says, “was one that I thought was important and compelling, because you had somebody who was motivated by this desire to serve, who had a contagious desire to serve.” He seems to allude to similarities between himself and Kennedy, saying, “You had somebody with a good popular touch but not afraid to be intellectual and, very significantly, somebody who had a generational appeal that was really powerful.”

The Kennedy comparison hasn’t been made much by the media—perhaps because we have compared one too many politicians to JFK and have learned our lesson. But Buttigieg is arguably the most Kennedyesque candidate in a field of 20. Kennedy remains our nation’s second-youngest president; Buttigieg would be our youngest. Kennedy made history as the first Catholic president; Buttigieg would be our first openly gay president. More than anything, Kennedy had an endearing quality. You wanted to be around the man and felt you were a part of something by supporting him. Buttigieg’s supporters seem to have a similar fixation. Several long months lie between this paltry Kennedy comparison and the ballot box, but Buttigieg looks as good as anybody in the race. And after the debates, we may finally have a front-runner.


Alex Thomas
Alex Thomas
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