Could Pete Buttigieg Become the First Millennial President?

Meet the mayor of South Bend, Ind., who wants to be the first member of his generation to run the country
Pete Buttigieg, who was first elected at age 29, is a two-term mayor of South Bend, Ind.
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Photos by Joshua Lott

Just before 10 on a balmy Sunday morning in mid-October, right on time, Pete Buttigieg marches into a squat brown building on the edge of Colonial Williamsburg, ready to fire up a group of door-knocking volunteers for Elaine Luria, a former Navy commander challenging a scandal-plagued Republican for a U.S. House seat from Virginia. Inside he comes upon a mere half-dozen bleary-eyed folks milling around Luria’s headquarters. They seem not quite sure just who this perky young dude in the crisp white shirt, blue tie and neatly pressed slacks might be.

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The local field organizer is full of apologies. “We had 10 people email this morning and say they couldn’t come because of the storm,” she says. A surprise weather system had blasted through two nights earlier on the tail of Hurricane Michael, felling pine trees and downing power lines. “It was like, ‘I haven’t had a shower in days and I just can’t.’ But we’re so glad to have you!”

Pete Buttigieg, who was first elected at age 29, is a two-term mayor of South Bend, Ind.

Buttigieg, the wunderkind mayor of South Bend, Ind., and one of the longest of 2020 presidential long shots, knew about the storm. His plane from Chicago had been delayed by the bad weather on Friday night, finally touching down in Charleston, S.C., at 3 a.m. After three Saturday events in the Carolinas, he had driven five hours through the night with Matt McKenna, his lanky and eternally patient young aide, only to find most of Williamsburg’s tourist hotels booked solid with local families and work crews. Somebody forgot to make reservations. For the second straight morning, Buttigieg has had to skip his 6 a.m. run. He’s just learned that his second planned event of the day, another pep talk for another congressional candidate in Richmond, has been canceled.

In short, his trial campaign run through the South is not proceeding quite as planned. But there are seven people here to inspire and impress — eight, if you count me — and Buttigieg is not one to waste an opportunity.

“I’m glad too!” he says, and does the politician thing he has perfected despite his innate shyness: He trains his full attention on everyone in turn, peppering them with questions about their lives, the power outages, the poll numbers, how folks are responding when they come knocking, the provenance of this bland office suite. “What did this place used to be before the campaign?” he asks.

“A dentist’s office?” one of the young women replies. “And I think a massage parlor.”

A normal politician might be miffed at the low turnout. A regular human being might not be looking quite so bright-eyed and bushy-tailed under the circumstances. But “normal” and “regular” are not adjectives that apply to the son of a Maltese immigrant father and an Army brat mom who grew up in decaying South Bend, got himself into Harvard, summer-interned for Ted Kennedy, worked for John Kerry’s presidential campaign, won a Rhodes Scholarship, learned Arabic in Tunisia, landed a jet-setting consultant’s job, left it to return to his beat-up hometown and become the youngest mayor of a midsize U.S. city, transformed that city into a national model of renewal, and then — deep breath — volunteered for active duty in Afghanistan while serving as mayor, came out as gay in the local newspaper, married a schoolteacher live on YouTube, turned heads in a dark-horse bid to lead the Democratic National Committee, and had the New York Times’s Frank Bruni gushing about him as potentially the “First Gay President”— all by age 36.

[Pete Buttigieg, citing need for generational change, joins 2020 Democratic presidential race]

Buttigieg, in fact, appears intent on proving Bruni right far sooner than the columnist might have expected; he’s currently making all the moves one would expect from an about-to-declare 2020 candidate. But he won’t be hinging his long-shot bid on the prospect of being the first openly gay president. Instead, he’ll be running as the herald of a new generation.

Buttigieg performs a marriage ceremony in his mayoral office for Catherine Pittman, left, and Victoria Powers.

Millennials became the country’s largest voting-age cohort in 2018, displacing baby boomers — and their politics break sharply with their parents’ and grandparents’. (Opinions vary as to where the millennial generation technically begins and ends, but the Pew Research Center defines it as those born between 1981 and 1996. Buttigieg was born in 1982.) This group not only leans heavily Democratic, but emphatically leftward. Of course, they overwhelmingly tell pollsters, gay people should be able to marry. Of course black and brown people have been shortchanged throughout history and continue to be. Of course immigrants do nothing but make the country stronger. Of course the government owes every citizen decent health care. And of course climate change is humanity’s greatest peril.

“The center of gravity of the American people is way to the left of the center of gravity of Congress and, in many ways, to the left of the national Democratic Party,” Buttigieg had told me earlier in the year. That’s especially true of millennials. Their political outlook is shaped by being the first post-World War II generation to face diminished economic prospects, and also the first to fully experience the diminished quality of life wrought by decades of tax-slashing, privatization and deregulation: inefficient social services, unaffordable child care, crummy roads and trains and public transportation, slow Internet speeds, and a rapidly warming Earth. Buttigieg’s peers are eager to embrace a politics that’s bigger and more ambitious — more New Deal than New Democrat. They want swing-for-the-fences solutions from politicians who don’t pretend that all the country needs is just some minor tweaks.

“Donald Trump got elected because, in his twisted way, he pointed out the huge troubles in our economy and our democracy,” Buttigieg says. “At least he didn’t go around saying that America was already great, like Hillary did.”

The mistake Democrats risk making in 2020, he says, is looking in the rearview mirror for solutions. “I get the urge people will have after Trump. ‘Look at the chaos and the exhaustion: Wouldn’t it be better to go back to something more stable with somebody we know?’ But there’s no going back to a pre-Trump universe. We can’t be saying the system will be fine again just like it was. Because that’s not true; it wasn’t fine. Not if we could careen into this kind of politics.”

Buttigieg, who was elected South Bend mayor in 2011, will not run for a third term.

After a 10-minute wait to see who else might turn up, a bushy-bearded Afghanistan veteran in a hoodie is called upon to introduce the special guest and mangles his name four different ways. Buttigieg (buddha-judge) just beams. “You can call me Pete; everybody does,” he says. He stands and delivers a condensed version of the talk he’s been giving around the country since the summer, mostly in support of the 20 first-time House candidates in red districts that he’s backing with his super PAC, Hitting Home.
Then he watches the organizer run through her tips for the day, looking as rapt as an eager first-time canvasser. “What’s that behind you?” he asks, pointing to a big sheet of paper tacked on the wall with names and messages scrawled all over it. The volunteers are asked to sign it when they come to canvass, the organizer says. “We’re going to give it to Elaine after she wins.”

“That,” he says, “is an incredible idea.”

I figure he’s just being super polite, but after we make our exit and he takes the wheel of his rented SUV — “You navigate, I’ll drive,” he tells McKenna; “I’ve always been terrible at land navigation” — it becomes clear that he wasn’t pretending. “That banner she’s having them sign, what a good way to build teamwork,” he says. “It’s the kind of thing that builds a sense that you’re all working together, and toward something. A good organizer knows about building a social culture in a campaign.”

With McKenna navigating from the back seat, we speed off with controlled aggression toward the interstate and two fundraisers in Northern Virginia. “It’s a shame about Richmond, but we’ll have more time to talk this way,” Buttigieg says. “I have to make a couple of calls, just so you know. I figure what we ought to do is we’ll find a place with a decent lunch. There should be good barbecue in this part of Virginia, right? As long as we’re in Fairfax by 3 o’clock or so we’ll be okay. So I’m pretty much all yours. We can make this a rolling interview. So to speak!”

[Evangelicals helped get Trump into the White House. Pete Buttigieg believes the religious left will get him out.]

Rolling monologue is more like it. Buttigieg is a human data-processor, one very interesting topic suggesting the next, punctuated by observations about something he’s spotted out the window in passing. One minute he’s telling me about his plans for the rest of the midterm election season, then he’s asking me about the prospects for the campaigns I’ve covered, then he’s on to the theory of parks and recreation, the wonders of tax-increment financing, the time he drove a van for Al Gore and got lost in Boston, and the unpredictable dress codes at different kinds of campaign events. “I was underdressed for the fundraiser in Columbia. It turned out to be a very dignified thing at Don Fowler’s house” — the former DNC chief — “and now this morning, I felt overdressed with the tie with the volunteers. It took me years to calibrate my way around South Bend, and now I’m trying to crack the campaign dress code. I’m beginning to absorb the lifestyle of somebody who’s running. Most of our events have been surgical, flying in and out, but it’s going to be this way for the next three weeks and, hey, Matt, look! There’s the bucket trucks we saw in the parking lot last night, right? Maybe not the exact ones.”

Buttigieg speaks with Shatoria Adams, left, and Kenneth Garrett during a visit to Elkhart Plastics in South Bend.

Buttigieg can come off like a combination Boy Scout and lovable dork. You can easily imagine him in Silicon Valley, deeply debating the future of artificial intelligence with his college friend Mark Zuckerberg before leaving work to feed the homeless. But politics has always been his main obsession. As a senior and student-government officer in high school, he won the 2000 JFK Profile in Courage Essay Contest, earning a trip to Boston for the annual ceremony. His subject was as millennial as it gets: Bernie Sanders.

“Candidates have discovered that it’s easier to be elected by not offending anyone rather than by impressing the voters,” he wrote. “Politicians are rushing for the center, careful not to stick their necks out on issues. Most Democrats shy away from the word ‘liberal’ like a horrid accusation.” But not the man from Vermont. “Sanders’ courage is evident in the first word he uses to describe himself: ‘Socialist.’ ”

Reading his paean to Bernie, it’s clear that young Buttigieg already had a streak of ambition and opportunism to match his idealism. “I have heard that no sensible young person today would want to give his or her life to public service,” the senior-class president and valedictorian of St. Joseph High concluded. “I can personally assure you this is untrue.” And it paid off: At the award ceremony in Boston, Ted Kennedy offered him a summer internship on the spot. That first wide-eyed taste of Washington after his freshman year at Harvard set him on the path that could soon, improbably enough, have him facing off against the once-obscure socialist congressman who struck him, 18 years ago, as both immensely admirable and impossibly old.

Buttigieg at the Progress Iowa holiday party in December. His appearance there signaled his intentions to political observers.

The departure of the Clintons kind of uncorks a new energy,” Buttigieg is saying as we rattle up the interstate. “It’s an exciting time to be a Democrat. The party has to figure out what it means now.”

He’d endorsed Hillary Clinton after her nomination in 2016, as any aspiring party leader must, but he clearly won’t be writing any laudatory essays about her campaign. “I organized a Union Hall event for her in South Bend,” he says, and shakes his head. “You could just tell the enthusiasm wasn’t there.” The problem, he says, was partly that the stakes seemed too low. “We need a bigger scope of ambition for people to rally around.” A return to the Clinton and Obama style of centrist incrementalism, he says, will invite disaster just as surely in 2020. “Change is something we need to face with clear eyes. It’s scary, but it’s also exciting.”

He paints his potential presidential campaign as a kind of blown-up version of his first run for mayor. Buttigieg announced his 2011 campaign two weeks after Newsweek featured South Bend as one of “America’s Dying Cities.” People had been promised a return of manufacturing jobs for almost half a century, Buttigieg says — “a little like Trump in coal country.” From 1902 to 1963, the city was the home of carmaker Studebaker, which employed nearly 25,000 local workers at its peak, before going belly-up. The city never recovered. When he was growing up, “a lot of people would still talk about the closure like it happened yesterday,” he says. “When I ran, we had to paint a picture of the future that did not translate into nostalgia.”

He points with particular pride to the massive infrastructure projects he undertook: refashioning the old, decaying Studebaker building into a hub for small “creative industries” like tech start-ups, and pledging that “1,000 homes in 1,000 days” would either be razed or refurbished to rid neighborhoods of the crumbling vestiges of the past. “The word ‘again’ was not part of our vision,” he says. “The message from the start was, ‘The Studebaker plant isn’t coming back, but we are, and here’s how.’ ”

Buttigieg knew that if he could make good on his audacious promises, he could also make a name for himself — which he quickly proceeded to do, beating the 1,000-day target and spiffing up the old plant over the harrumphs of the city council veterans and longtime government officials who couldn’t help resenting the technocratic kid from the fancy schools and the global consultancy.

As we proceed through Virginia, interstate traffic, as it’s wont to do, repeatedly bottles up for no apparent reason. We’ve still got plenty of time to get to Fairfax County for the first event up there, but the creeping pace is driving Buttigieg to distraction. “Let’s find an alternate route,” he says.

“Okay. Two miles and you’re going to hop on 301,” McKenna says.

“Got it,” Buttigieg responds. “Wow, this needs resurfacing. There’s a Nobel Prize waiting for someone who can figure out how to make asphalt last longer than 12 years. I’m not kidding. I really think there ought to be a Manhattan Project for this. It’s classic market failure.”

Buttigieg “has a magnetism about him. ... I think his age is an advantage,” says former DNC chairman Howard Dean.

If Buttigieg becomes president, you sense, the future will be chock-full of Manhattan Projects. But first he has to overcome the considerable odds and find a way to win. He has clearly made a close study of how Barack Obama, Bill Clinton and John F. Kennedy took their nontraditional paths to the presidency at young ages. “When you run young, your face says you represent change,” he says. But he doesn’t want to stop at symbolism: His message for 2020 will be centered on a clean, sharp break with the Lite Republicanism that Democrats embraced in the 1990s. While older voters still tell pollsters they favor keeping taxes low and ambitions modest, millennials overwhelmingly support Medicare-for-all, free college, heavy spending to tackle poverty and climate change, and major infrastructure investments — social democracy, in a nutshell.

[In a coastal state with 4.5 million Trump voters, Pete Buttigieg says coastal states don’t know Trump voters]

Though Buttigieg prefers to label himself — if he must label himself — a “progressive Democrat,” he can deliver a spontaneous dissertation on why young Americans say they prefer socialism to capitalism that would do Rep. Alexandria Ocasio-Cortez proud. Nobody should mistake it for youthful idealism or recklessness, he says. “I think the new generation that emerges now will have a different kind of seriousness about the future,” he says. “It’s more immediate and personal, the younger you are. You’re going to be on the business end of climate change, of tax cuts; you’re going to be touched more by our post-9/11 wars. Matt, how old were you on 9/11?”

“Um, let’s see — I was 5.”

“That’s what I mean. You can be a grown-a– man like Matt here and don’t recall us not being at war. Which is a whole ’nother part of it. Look how many candidates this year” — including 11 of the House candidates he’s been boosting — “are young veterans. I think the sense of obligation kicked in, the awareness that it’s part of a civic duty and a moral failure when you only have other people fighting your wars. And in my case, that included a lot of the people I was commanding in the reserves. That’s part of what pushed me into it. I thought, ‘Why not me?’ ”

“Why not me?” is also the way Buttigieg thinks about running for president. It’s no accident, he says, that this year’s Democratic field could include five other current and former mayors: Eric Garcetti of Los Angeles, Andrew Gillum of Tallahassee, Mitch Landrieu of New Orleans, Michael Bloomberg of New York and Julián Castro of San Antonio. With most state capitols every bit as clogged up in partisan stalemates as Washington, mayors still “actually get to do stuff,” as he puts it.

“The discussion in Washington has gotten so abstracted from reality,” he says. He wants to drive politics back toward the lived experiences of the citizenry, which don’t divide them the way ideological abstractions do. “What makes a country great, really? We like to talk about ‘freedom’ and ‘security’ and ‘family values’ or whatever,” he says. “But the measure of a country’s greatness is whether it helps people lead better lives, with less worry.”

Buttigieg takes a selfie with a customer outside Taqueria El Aguila in South Bend in December.

As soon as we’ve broken free of bottlenecks, Buttigieg starts searching the side of the highway for a lunch spot. South of Fredericksburg, he spots a low-slung, ramshackle series of structures: “Hey, there’s two things I’ve never seen paired: restaurant and thrift shop.” In a split second, he’s making a quick swerve left. “Let’s check it out!” he says, as McKenna lets out a little groan.

After a quick scan of the dingy thrift shop — “Matt, look, $7 suits!” — we follow him into Lou’s Soul Food, which smells like 30 years of fried food. “It’s a buffet,” he says, as if that settles things, and we find a table near the back to talk about his first campaign experience.

“Right after college I went to work for John Kerry, June of 2004. It was one of those deals where you graduate, pack a bag and go where they tell you. I thought I was going to D.C., so I moved there, started sleeping on a friend’s couch, and then got a phone call from Arizona: ‘I hear you’re my new research director.’ I’m like, ‘Oh, okay.’ They said, ‘Do you have a car?’ No, I didn’t. ‘Well, buy one tomorrow, start driving, and you can be here at work on Friday.’ So that’s what I did.”

When Kerry’s Arizona experiment floundered, “they pulled us, a month out from the election. I got reassigned. In classic campaign fashion, I thought I was supposed to go to Denver, so I drove eight hours to Denver, turned up at the office, introduced myself, carved out a desk space somewhere, called Washington and said, ‘Okay, now what?’ And they said, ‘Oh, Denver? We actually wanted you to go to Albuquerque.’ So that’s how I learned what a presidential campaign was actually like.”

After the Kerry campaign, Buttigieg went back to Washington for six months, biding his time “before the Rhodes Scholarship kicked in.” When he graduated from Oxford, he decided to give the business world a try and took a job at McKinsey, the prestigious global consulting firm. “I knew that I really didn’t understand the way the world worked,” he says. “How do people make money, operate and move around the world? How does this stuff work?”

In all the hours I’ve spent talking to Buttigieg, this is the first time I catch a whiff of disingenuousness. Companies like McKinsey, a little like their Silicon Valley compadres, are magnets for high-achieving Ivy Leaguers who like to talk about “making the world better” while raking in some serious salaries.

His 2020 message will be centered on a clean break with the Lite Republicanism that Democrats once embraced.

But Buttigieg, who worked out of Chicago and specialized in energy and economic development, didn’t make a career of it. He left McKinsey after three years and two extended leaves to door-knock for Obama in 2008 and serve as research director for the gubernatorial campaign of Indiana Democrat Jill Long Thompson.

In 2009, he got his dander up when Richard Mourdock, the Republican state treasurer facing reelection in Indiana, sued the Obama administration to block the auto bailout. “This was an insane thing for an elected official in Indiana to do,” Buttigieg says. “That made me start asking: Why don’t I run against this guy?”

Buttigieg’s “Meet Pete” campaign never took flight. He blew through his McKinsey savings and still got “clobbered,” losing by 25 points. “But in a way,” he says, “it was my first experience in winning by losing.” The defeat stung, “but I learned how to organize a team,” he says. And he learned that smarts weren’t the only secret to political success: “It matters more to understand human beings and how to reach them, how to move them.”

For all his aw-shucksiness, if Buttigieg has the least bit of doubt that he’s ready to make the leap to commander in chief, at an age that barely qualifies him constitutionally for the job, it’s impossible to detect. He has often been urged to run for Congress — the next logical steppingstone — but he sees it as a dead end. “I would find it demoralizing,” he says. David Axelrod, Obama’s political guru, is among the powerhouse Democrats who see no reason Buttigieg should wait. Axelrod’s first Pete sighting was in November 2015, when the young mayor was given the John F. Kennedy New Frontier Award at Harvard. “He spoke without a note in front of him and gave one of the most stirring speeches I’ve heard,” Axelrod told the South Bend Tribune. “He has that gift.” Axelrod has given Buttigieg the same advice he gave Obama after his famous Democratic National Convention keynote speech in 2004: The biggest mistake politicians make is missing their moment by hesitating.

When Buttigieg decided to undertake the DNC race in 2017 — gambling that if he couldn’t knock off Keith Ellison and Tom Perez, the favorites of the Sanders and Clinton camps, he could at least give his future a rocket-boost and once again win by losing — he debated circles around the two front-runners, and charmed cable-news viewers and grizzled party elders with his unexpected eloquence and fresh vision for the party, which included a bundle of bright ideas for digital strategies. Right before the vote, headed for a third-place finish, he bowed out and returned to South Bend with enough new backers to form a super PAC that would give him an excuse to travel the country in 2018 and lay the groundwork for 2020.

“He might very well have won the DNC race if you could have had a secret ballot,” says Howard Dean, who endorsed Buttigieg for his old job. “But it’s such an insider race. … That was hard to overcome.” Dean, who has spoken with Buttigieg about his own experience vaulting from obscurity to the top of the 2004 Democratic primaries, sees a lot of Obama­esque qualities in the mayor. “He has a magnetism about him,” he says. “And I think he projects this idea of, ‘Let’s get past all this partisan crap and do something for the country for a change.’ I think his age is an advantage. I really think the American people would like to see our generation step aside and see a new generation take leadership.”

Obama is also a Buttigieg fan. In his 2017 New Yorker exit interview, the former president named Buttigieg as one of four Democrats who would lead the party forward. They’ve met at least once to discuss the future.

According to Buttigieg’s husband, Chasten Buttigieg, there’s another Obama parallel that most people wouldn’t guess from Pete’s genial retail politicking and smooth style on the stump: “He’s definitely an introvert. And he’s still coming out of some of his shells.” That’s something he’s learned in part from Chasten, who does improv comedy on the side and maintains a busy Twitter feed that can be flat-out hilarious. “When we go out, we’ll go to events and then I’d want to keep going out to a bar for a beer,” Chasten says. “And he’ll be wanting to go home and curl up with a book.”

While Buttigieg frames his sexual orientation as part of his next-generation appeal, he finds it uncomfortable to talk about why it took him so long — until he was 33, and back from Afghanistan — to “accept the plain fact that I’m gay.” When he spoke to Axelrod for his podcast, “The Axe Files,” in March 2017, his silver tongue abandoned him as he tried to explain. “If willpower alone could make somebody straight, you know … I would’ve —.” He didn’t complete the thought but acknowledged that his struggle had something to do with his “political aspirations” and his desire to serve in the military while “don’t ask, don’t tell” was still in effect.

But once he finally abandoned the struggle, Buttigieg was characteristically all in. He came out in the South Bend Tribune during his mayoral reelection campaign, soon after then-Gov. Mike Pence signed his infamously anti-gay Religious Freedom Restoration Act. And in short order he met Chasten online and quickly fell in love. When the two wed in June 2018, they timed it for Pride Week. The ceremony was live-streamed on YouTube — and afterward, the couple joined revelers at a Pride block party, with a New York Times reporter in tow.

Still, Buttigieg doesn’t much care for being identified primarily as the “first gay” anything. Millennials are supposed to be obsessed with identity politics, but Buttigieg thinks that Democrats make a serious mistake when they slice-and-dice their message to appeal to particular identities. “Along the way, the party fell into this pattern of thinking we should have a message for each constituency,” he says. “But the reality is that people care about issues that aren’t ‘their’ issues, quote unquote. Elderly residents care about education. Suburban women care about racial justice. Young people care about social programs for the elderly.”

Buttigieg at home with his husband, Chasten, and their dogs Buddy, left, and Truman.

I’ve ridden along with candidates for decades and have long since grown accustomed to the interview pausing when they approach the next event. This is the time for a tense, whispering huddle with aides, reviewing talking points and notes on the pols and donors who need impressing. Buttigieg, by contrast, grows practically giddy the closer we get to the first event in Northern Virginia, taking only a minute to quiz McKenna on the essentials of the fundraiser for Jennifer Wexton, a young Virginia state senator challenging Republican Barbara Comstock for her U.S. House seat.

Earlier in the day, Buttigieg had told me how much he relishes coming into an environment like this, where “nobody knows me from Adam,” and seeing what happens when he starts speaking. “Sometimes you can watch people as you go up to the podium and they’re like, ‘What’s the deal with this guy?’ And then it’s, ‘Okay, he’s up there, he can talk.’ If it’s going right, I love to watch the faces then: Partly I like to study them to see what’s working and not, what to cut out next time or maybe expand. But there’s this look, when you know you really have them. It’s hard to describe, but it’s unmistakable.”

This time, the turnout is clearly not going to be a disappointment; we start to see the lines of very nice parked cars a couple of blocks before we reach the McMansion that is our destination. Inside, the vast open living, dining and kitchen space is jammed with well-off white people in high cocktail mode. Only Wexton recognizes the special guest, and they chat briefly before the folks are hushed and Buttigieg (pronounced properly) is introduced.

Standing in front of a big fireplace and a huge TV showing the Redskins game on mute, Buttigieg is in his element, opening with some banter about where he’s from — “You might know us for our football team” — before segueing into the message he’s honing for 2020. “It’s very important for people in communities like mine to know there’s a formula for moving forward that isn’t resentment, that isn’t nostalgia,” he says, recounting his first campaign for mayor. “We didn’t go around saying we’re going to make South Bend great again.” The folks laugh heartily at the implicit dig at Trump. “I didn’t go around thumping my chest saying I alone can fix it. We came together and identified problem-solvers to get things done and actually change the trajectory of our future.”

I’m watching the faces he’s watching, seeing folks whisper low to their spouses: Who is this guy again?

“We’re finding a whole new vocabulary for why people should vote,” Buttigieg is saying. “We’re reclaiming some territory that our party, in my opinion, foolishly left to the other side. Like freedom, right? The so-called Freedom Caucus, as you know, has the most fanatical members of Congress. But they don’t seem to know that you’re not free if you can’t change jobs because you’ll lose your health care. And that you’re not free if you can’t sue a credit-card company that’s ripping you off. And you’re certainly not free if somebody you’ve never met gets to tell you who you can and can’t marry based on their interpretation of their religion.”

There’s one little hitch in the performance, when he praises Wexton for being in the minority in the state assembly and still passing four pieces of major legislation. (“Actually, it’s 40,” she says, interjecting with a smile but an unmistakable note of sharpness.) Buttigieg plays it off laughingly, saying he’s so much more impressed with her now, since “in our legislature back home, four bills for a Democrat would be quite a feat,” and hands over the mic to the candidate, who smiles a bit warily, looking like she knows she’s been upstaged.

When Wexton finishes her spiel, Buttigieg is mobbed by wine-sipping admirers. It takes McKenna a bit of elbowing and sorry-ing to push his way near enough to start nudging his man out the door; there’s another crowd of tony Democrats waiting on the other side of Fairfax County. Buttigieg grips and grins his way out the door, feeling that feeling. As we bustle out to the SUV, he looks over at me and says, “Yep. You saw that, right?”

Buttigieg with staff members, from left, Laura O'Sullivan, Mark Bode and Suzanna Fritzberg.

During our day trip in October, Buttigieg was coy about his plans for the future. But on Dec. 20, three days after announcing that he wouldn’t run for a third term in South Bend, he spoke at the annual Progress Iowa holiday party in Des Moines — signaling his intentions to political observers. In January, he hired Marcus Switzer, Hillary Clinton’s 2016 deputy finance director. And in February, following the release of his book, “Shortest Way Home: One Mayor’s Challenge and a Model for America’s Future,” Buttigieg plans to strike out across the country on what will likely amount to an exploratory campaign for the presidency.

He knows that the effort might add up to nothing more than one more instance of winning by losing — raising his profile for whatever else might lie ahead. But he’s calculating that the whole bundle of “firsts” he represents will make him stand out from the pack of senior citizens — Joe Biden, Elizabeth Warren, Bloomberg, Sanders — and the football-team’s worth of middle-aged members of Congress harboring White House dreams.

While others might see his age and inexperience as fatal liabilities, Buttigieg recognizes that the path to the White House often evolves. It’s actually been a very long time since Democrats recaptured power without a candidate who didn’t represent a departure from political norms: the young, Catholic JFK; the up-from-nowhere Southerner Jimmy Carter; the “New Democrat” Bill Clinton; and Barack Obama, the African American just a few years removed from being an Illinois state senator.

Could it now be time for a millennial? When we catch up in early December, Buttigieg says he saw “glimmers” of it in 2018: “We saw indications that it’s okay to talk about our values as Democrats again. That the politics of conviction that appealed to young people, with Bernie in 2016, can also be articulated successfully by the next generation.”

I mention that the day before, Biden, on his own book tour, had proclaimed himself “the most qualified person in the country to be president.” Buttigieg laughs. “So was Hillary,” he says. Game on.

Bob Moser is a writer in Beacon, N.Y.


Credits: Story by Bob Moser. Photos by Joshua Lott. Designed by Michael Johnson. Photo Editing by Dudley M. Brooks.