Some weeks later, on a dreary day in April, Zuckerberg and Buttigieg were sitting in the mayor’s Jeep as Zuckerberg fiddled with the Facebook Live video stream. Buttigieg, wearing a too-big bomber jacket, gave his famous guest a tour of the Rust Belt city, gamely describing the city’s revival—how an old Studebaker factory site was being repurposed into a data center, how downtown’s one-way streets had been redesigned to slow city traffic and foster human connection. They stopped for coffee at a pay-it-forward place, and had lunch at a family-owned tavern in a largely Latino, working-class part of the city. One of Zuckerberg’s spokespeople described the pair as “friends” to the local reporters who were there to chronicle this visitation from the world’s most powerful social media executive.

But this was not a reunion of college buds. In fact, it was more like the beginning of a relationship that has evolved in unexpected ways over the past three years as these two precociously talented and ambitious young men have asserted themselves on the national stage.

Zuckerberg, class of 2006, and Buttigieg, class of 2004, overlapped for two years at Harvard but ran in largely separate circles. Zuckerberg was a Phillips Exeter kid from Westchester, New York, obsessed with building computer games and proto-networking tools. Buttigieg was student body president at the co-ed Roman Catholic St. Joseph’s High School, a Midwesterner with a deep interest in public service who’d applied to Harvard sight unseen. Zuckerberg and Buttigieg wouldn’t meet, and then only fleeting, until the 2012 New York wedding of another mutual Harvard friend: Facebook co-founder Chris Hughes.

At the time their paths crossed for a few hours in South Bend, Zuckerberg was struggling to defend himself and his company against growing blowback over the 2016 U.S. presidential election. Some wondered if this tour wasn’t laying groundwork for a presidential run of his own. Buttigieg, meanwhile, had only recently fallen short in his bid to become chairman of the Democratic National Committee. Hosting the tech luminary was a helpful shot of positive national publicity at a moment when he was beginning to explore his options for wider office.

Now three years later, their relationship is the subject of ramped-up speculation and interest. Zuckerberg is still one of the technology world’s most powerful figures, but his half-trillion-dollar company is facing unprecedented threats, as calls grow to break it apart. And, surprisingly, it’s Buttigieg who has mounted a top-tier presidential campaign.

And suddenly, the connection between Zuckerberg and Buttigieg, as tenuous as it might be, matters for both men—and for the country. Politically, beating up on tech firms has become a winning populist move. But tech leaders can still be powerful and wealthy allies—and in an election stuffed with aging Boomers, there’s also appeal in the idea of a digital-native leader who can bring tech giants to the table and speak to them in their own language.

For now, Buttigieg seems to be keeping the tech world close but Facebook at a distance.

Buttigieg has drawn considerable financial support from Silicon Valley for his White House bid, and Zuckerberg and his wife drew headlines when they recommended staffers to the campaign. But Buttigieg has in recent months begun to speak out more forcefully about the need to constrain the power of both Facebook and Zuckerberg. In the midst of a massively consequential election that could hinge in no small measure on the decisions Zuckerberg makes about how his platform handles political ads, their relationship is evolving—and not necessarily in a friendlier way. In an interview with the New York Times editorial board in January. Buttigieg criticized what he called Facebook’s “refusal to accept their responsibility for speech that they make money from.”

The Buttigieg campaign says that the two haven’t spoken for a year and a half, a characterization Facebook doesn’t dispute. Buttigieg said a year ago that he and Zuckerberg have been in touch “every now and then,” but clarified Sean Savett, a Buttigieg campaign spokesperson, “They haven’t talked in over a year, or since, really, Pete’s run for president.”

Back in the mid-aughts, Zuckerberg was holed up in his dorm at a desk scattered with empty Snapple bottles, building, first, FaceMash, a site for ranking the attractiveness of his classmates, and then TheFacebook.com. Buttigieg, meanwhile, was angling to win election as president of Harvard’s Institute of Politics, the Kennedy family-endowed center that lets service-minded undergrads rub shoulders with political luminaries. Buttigieg got onto Facebook as one of the first few hundred users—facebook.com/287 still redirects to one of Buttigieg’s profiles—but he later recalled to New York Magazine, “I thought it was just another Harvard thing. We didn’t realize where it was going.”

Quickly, though, the scale and ambition of what Zuckerberg was up to would become clear. Facebook launched on February 4, 2004, and by December, it had grown beyond Harvard, and beyond the Ivies altogether, amassing more than a million users. A Harvard friend of Zuckerberg says that what Mark had pulled off, at age 19, quickly became an inspiration on campus. If Mark can conquer the Internet, what world changing can the rest of us get busy doing? “There was this draw—that it was such a huge success that it was like, ‘Oh, I can do that, too,’” says the friend, Sam Lessin, who went on to spend four years at Facebook, ending up as the vice president of product management. “It was part of the atmosphere.”

But while Zuckerberg was, in those days, on the cusp of changing the world, he had little interest in doing it through traditional means. “After [the] summer of ’03, I thought social networking should be applied to politics,” Joe Green said in an interview in 2007. He says he pitched his college dormmate on the idea. “Instead he built Facebook. That was clearly a bad choice,” Green joked.

“He asked me to be his partner,” Green said. “I instead went to work for [John] Kerry.”

It was the summer of 2004, and Zuckerberg, who’d had run-ins with Harvard administrators over copying photos from the school’s network to build FaceMash, decided to drop out of the university and make a go of his site out in California. Buttigieg, 22, had graduated, and was eager to get some experience out on the campaign trail. Green, 21, was still wrestling with his decision (under some pressure from his father) to not go west with Zuckerberg, who didn’t seem especially contrite over the FaceMash episode. (Zuckerberg would later laughingly recall that during the dramatic night in his Kirkland House dorm room when he was scrambling to deal with the FaceMash aftermath, “Joe comes in and takes our last Hot Pocket.”) In a move that might have cost him hundreds of millions of dollars, Green joined a crew of politicos being put together by Mike Moffo, whose brother Chris had gone to Harvard, to work on Democratic presidential nominee John Kerry’s bid to pull off an unlikely primary win in Arizona.

Arizona was a third-tier state for Kerry, and thus an opening for aspiring but inexperienced politics junkies. Housed in the squat state-party headquarters in Phoenix “that lost Internet every time it rained,” recalls Kate Gallego, the Arizona for Kerry campaign has gained over time a reputation as an all-star squad. Gallego (Harvard ’04), who worked on legislative issues for the state party, is now mayor of Phoenix. Rohit Chopra (Harvard ’04) was deputy field director and one of Green’s bosses; he’s now a commissioner on the Federal Trade Commission. Moffo would go on to be deputy field director for the successful 2008 Obama campaign. Doug Wilson was the state director; he now is a foreign policy lead for the Buttigieg campaign.

But even among that crew, Buttigieg, who worked on research and communications for the campaign, had an aura. “You got the impression that he was a total rock star,” says Jesse Gabriel, now a California assembly member. “He was very serious, very thoughtful, and he just had a gravitas about him in a way that struck me that he was going to go onto big things.”

Green, meanwhile, was field organizing out in Lake Havasu City, a Spring Break spot on the Colorado River in rural Arizona. Says Gabriel of Green, “he was this sort of lovable and crazy guy. He always had wild stories and was getting into all kinds of weird situations. I think he was living in an underground bunker part of the time. But Joe is also deeply intellectual, and very, very smart.” (Green confirms he did spend part of the time living subterraneanly.)

Still, Green and Buttigieg, however odd a pair they were, stayed close. Says Gabriel, “they’re the kind of guys who could, you know, have a beer and talk de Tocqueville.”

Arizona grew out of reach for Kerry and the band broke up.

Buttigieg would go build his résumé, first at Oxford as a Rhodes Scholar and later as a McKinsey consultant based out of Chicago before heading home to South Bend. Green would return to Harvard, spending years as a startup founder working on the idea that social networks could be used for politics. It was a truth proven when Chris Hughes—a friend of Buttigieg’s and a roommate of Zuckerberg’s who had, after graduating, headed west with Zuckerberg to launch Facebook—left the company in 2007 to join the Obama campaign. Hughes built MyBarackObama.com, using the social tools he learned at Zuckerberg’s side, to recruit and deploy thousands of supporters, as well as fundraise millions of dollars. Asked about it at the time, Obama said, “there’s no more powerful tool for grassroots organizing than the Internet.”

Meanwhile, Zuckerberg was turning Facebook into a global behemoth and transforming himself, despite his professed lack of interest in politics, into a person with considerable political clout. By 2011, with Facebook at more than 750 million users, Zuckerberg was dining with President Obama and other Silicon Valley leaders decades his senior, and hosting a convivial mock town hall with Obama at Facebook’s California headquarters. In 2013, Zuckerberg’s eye began turning more intentionally toward politics and policy. He launched Fwd.us, a pro-immigration group, and installed Green as its head. Zuckerberg’s name was known all over the world, and his star was ascendant.

Buttigieg, meanwhile, had a less eye-catching trajectory. In 2010, he had run for Indiana state treasurer and lost, though the next year he rebounded to win a race for mayor of his hometown—a humble city of a little over 100,000 people. He began building a reputation a forward-looking politician dedicated to creatively repurposing his Rust Belt city. One source of inspiration: Facebook. In a TED talk at Notre Dame during his first term, Buttigieg cited the site as an example of turning something old—a student directory—into something innovative. (Zuckerberg, he said, was “just a guy in the next dorm over from mine, a guy who now has a lot more money than I do.”) Buttigieg won reelection in 2015, and two years later he launched a long-shot bid to head the Democratic National Committee, a party organization still rocked by Donald Trump’s once-unthinkable presidential victory.

By late February, it was clear that Buttigieg wasn’t going to win the DNC race, and so he dropped out. Then Zuckerberg himself came calling.

For years, Zuckerberg had dedicated himself to annual challenges. One year, it was learning Mandarin. Another, eating only meat from animals he had personally killed and butchered.

At the start of 2017, Zuckerberg declared that he intended to meet that year with people from all 50 U.S. states. No more virtual connection, he would do it in person … sort of like a politician. Immediately, the pledge raised speculation that Zuckerberg was laying the groundwork for a national campaign of his own. Those close to Zuckerberg insisted that wasn’t the case; concern over so-called fake news on Facebook its role in swaying the 2016 presidential election was growing into anger, and Zuckerberg was trying to come to terms with the social and political impact of the site he’d always approached with the cool detachment of an engineer.

Zuckerberg said as much. “After a tumultuous last year, my hope for this challenge is to get out and talk to more people about how they're living, working and thinking about the future,” he wrote in a blog post announcing the project. Zuckerberg went on to say that, in his judgment, the forces of technology and globalization have “contributed to a greater sense of division than I have ever felt in my lifetime,” and “we need to find a way to change the game so it works for everyone.”

Zuckerberg started his year of travel in Texas, where he met with local police in Dallas, went to the rodeo in Fort Worth, and ate with community leaders in Waxahachie. During a later, Southern tour, he visited a shrimp boat in Alabama, walked a Civil War battlefield in Mississippi, and took in New Orleans’ Ninth Ward. He visited a South Carolina church that had been terrorized by a mass shooting and drove NASCAR in North Carolina. As winter turned to spring, Zuckerberg’s team was eyeing a Midwest swing, and Indiana was still on his to-be-visited list. It was then that Zuckerberg got in touch with Buttigieg, albeit through Green, who had turned into a liaison for Zuckerberg to the political world. Buttigieg, Green discovered, may have been an admirer of Zuckerberg, but that didn’t necessarily mean he was some kind of super-user. “I don’t think he was the most active social-media person,” Green says.

During the Saturday visit, Buttigieg drove, and Zuckerberg rode shotgun in the mayor’s Jeep, with the Facebook CEO attempting, with some trouble, to provide real-time video of their travels using Facebook Live. (Live commentators asked why it looked like Buttigieg was on the right side of the car; Zuckerberg, looking a bit chastened, explained that Facebook Live flips its feed.) Buttigieg was the star, with Zuckerberg teeing up questions like, “Pete, do you want to just give a bit of your background, and how you came to be mayor here?”

They hit a community-run coffee shop and a juvenile justice center, toured some of Buttigieg’s “smart streets” project sites, and drove by the city’s old Studebaker factory. They lunched at Simeri’s Old Town Tap, where the pair enjoyed the $3.95 bowl of “Famous Hungarian Goulash,” a server at the bar told me. Zuckerberg was gone by evening, off to have dinner with firefighters in the nearby town of Elkhart.

Buttigieg tweeted out a link to a local news story on Zuckerberg’s visit, commenting, “You know, another day in South Bend…”

That visit seems almost quaint now.

Not long afterward, anger at Facebook would bubble over, with Zuckerberg personally coming under fire for the idea that he looked the other way while Russian actors used his social network to corrupt the 2016 election. That controversy fed others, and the outrage directed at the company in political circles has only grown in the years since. Trump and others on the right routinely accuse Facebook of being in the tank for liberals—seemingly as a way of keeping the company on its toes. Meanwhile, many on the left have developed real ire toward Facebook over its policy of allowing misleading political ads and posts on its site, which they view as kowtowing to Trump.

That was the context in which the news came in October that Zuckerberg and his wife, the pediatrician and philanthropist Priscilla Chan, had recommended two staffers to the Buttigieg campaign. All involved sought to downplay the situation. On a press call shortly afterward, Zuckerberg said it would be a mistake to take it as some sort of endorsement, saying, “this probably should not be misconstrued as if I’m, like, deeply involved in trying to support their campaign or something like that.”

Sean Savett, the Buttigieg campaign spokesman, said Zuckerberg and Chan reached out to the campaign to recommend the staffers—one a data scientist from Facebook, one an Indiana native from their Chan-Zuckerberg Initiative—after they expressed interest in working for Buttigieg. “That’s a pretty standard thing—you know, if you want to work for a campaign, you try to use all of the levers and networks that are possible.”

“A lot of people were like, ‘Oh my god, Mark and [Priscilla] are doing HR for the campaign,’” says Savett. “He sent a recommendation email, and his wife sent a recommendation email for two people they knew who were applying, like pretty much any former boss would if you were on good terms,” Savett says. “And they didn’t even reach out to Pete for that. They reached out to one of Pete’s aides,” campaign manager Mike Schmul, who Zuckerberg had met on his South Bend visit.

But Facebook, by that point, had become politically toxic in some quarters, and Zuckerberg’s dabbling in politics had become fraught.

Even some of those once closest to the company have turned on it.

Facebook made Chris Hughes rich, with his net worth reportedly nearing a half-billion dollars. But today he’s one of the company’s harshest critics, calling for the company to be broken up. In an op-ed in May of 2019, Hughes said that since the last time he’d seen Zuckerberg, in the summer of 2017, “Mark’s personal reputation and the reputation of Facebook have taken a nose-dive,” and that while he hadn’t worked there for a decade, “I feel a sense of anger and responsibility.”

Buttigieg has drawn considerable support from Silicon Valley, with some in that engineer-soaked ecosystem seeing in him a like-minded solutions-oriented and long-term thinker, an appealing blend of technocrat and optimist who sees no problem that can’t be carefully parsed. It doesn’t hurt that, at 38, Buttigieg is the contemporary of many of the tech industry’s most prominent leaders—sandwiched, for example, between the 35-year-old Zuckerberg and 43-year-old Twitter CEO Jack Dorsey. His national finance chair is a prominent figure in Silicon Valley: Swati Mylavarapu, a venture capitalist who, with her husband, Nest co-founder Matt Rogers, runs the VC firm Incite. Netflix CEO Reed Hastings has hosted a fundraiser for Buttigieg, and his high-profile donors include famed investor Ron Conway, Y Combinator’s Sam Altman, and Lowercase Capital’s Chris Sacca.

Today, Buttigieg is, says his campaign, closer both personally and ideologically to Hughes than he is to Zuckerberg. “Pete and Chris speak every few months,” Savett, the campaign spokesman, says. “Pete believes Chris has made a really compelling case about the concentration of power and that he’s made compelling arguments on a number of different issues, including the future of tech.”

Buttigieg hasn’t called for the company to be broken up; of the major Democratic candidates, only Elizabeth Warren and Bernie Sanders have gone that far—with others in the field calling it distinctly Trump-like to dictate to federal agencies, even hypothetically, specific companies to target. But Buttigieg has grown harsher and harsher about the company as time goes on.

Last February, Buttigieg, still a long-shot candidate, spoke of Facebook and Zuckerberg as a problem fixable with a smart policy tweak. Both, said Buttigieg, were “well-intentioned” but still reckoning with the consequences of their roles in the world. “I think they realized that there’s gotta be some kind of policy response, because what they do is increasingly a matter of policy. I mean, in many ways corporate policies of Google, Facebook, and the others are public policy. And I think they take that seriously, I’m sure he does.”

But some 11 months later, with Buttigieg rising dramatically in the polls—and amid Facebook unveiling a series of controversial policy decisions on how to approach the 2020 election—Buttigieg grew much harsher. Just because he knew Zuckerberg, the candidate said, “doesn’t mean we agree on a lot of things,” Buttigieg said in an interview with the New York Times editorial board. Buttigieg had once praised social media for helping to introduce him to his husband, Chasten; Hinge, the dating app they used to meet each other, at the time used Facebook’s network of social connections. Now he was calling into question Facebook’s entire ad-based business model.

Said Buttigieg of Zuckerberg, “no one should have that kind of power.”