Shortest Way Home: One Mayor's Challenge and a Model for America's Future

TO ME THESE IDEAS SEEMED CLEAR, almost to the point of being obvious. But few others in the national conversation seemed to be making that case. So, as a second-term urban mayor just a few days shy of my thirty-fifth birthday, I did something that would not have crossed my mind two months earlier: began organizing a national campaign.

You might think such a small number of voters is easy to approach, but in some ways it’s harder, because each of them expects to hear from you personally. The election was in late February, which meant I had about two months to reach them all. Mathematically, this is certainly possible . . . if you assume half-hour calls at a rate of ten or fifteen calls a day. But that also assumes they actually pick up.

What happens, instead, is an enormous, nationwide game of phone tag. Of course, a few really do pick up, and you can have a straightforward conversation and ask for their support. But more likely you leave a message, or several. Or you try to schedule a call. Or they call you back, but you miss it because you’re on another call or they’re calling from Hawaii and it’s three in the morning.

Late to the game and racing against the deadline, I put together a staff to help bring order to the phone-call operation—not to mention logistics, press, volunteer management, and finance. On January 5, 2017, two weeks before the inauguration of President Trump, I officially became a candidate. Since this was a party post and not a public office, there was no big speech to give, or even a county clerk’s office where I could ritually go file papers. Instead, unglamorously, I just printed out a statement of interest in running, signed it, scanned it, and emailed it to someone at the DNC.

The dining room of our house on North Shore Drive became the initial headquarters. With Chasten and a couple soon-to-be campaign staff members around the table tracking social media and filling my call schedule, I spent my first day as a candidate on the phone with reporters, party figures, and potential supporters. Looking through the window at the sidewalk in the early January gloom, I told CNN that “not being afraid to talk about our values will resonate in places where we as a party have been struggling.” Pacing around the living room on rugs I’d brought back from Afghanistan, I told Tom Perez that I was getting in and why, and listened as he responded graciously and welcomed me to the race (as did each of the other candidates I would be competing with). Between bites of a Chipotle burrito, I tried to stay lucid through call after call, all the way through to a trip to the nearest satellite studio for a 10:40 p.m. appearance on MSNBC.

What followed was an eight-week sprint that took us to every corner of the country, with major candidate forums at a Phoenix hotel ballroom, a Houston college campus, a Detroit auditorium, and a Baltimore convention center. I held fundraisers in San Francisco, Los Angeles, New York, and Washington and made appearances in Miami and Chicago in the run-up to the big final DNC meeting in Atlanta where the vote would take place—all while continuing to go to my office on non-travel days to perform all the functions of mayor.

Every couple days we took on a new hire until the team grew to about a dozen. We attracted more and more attention as we went, and it became impossible to stay on top of all the incoming communication. My email in-box became impenetrable. If the phone rang and the caller ID said “Unknown,” I knew it was either a telemarketer or some one very important. At one point I picked up a call from an unfamiliar Vermont number, thinking it was Howard Dean (who had been encouraging me to run), and instead heard the voice of Bernie Sanders (who was calling to suggest I drop out and make room for Ellison). National figures I had never even met took an interest, as word reached me daily of new endorsements from figures ranging from North Dakota Senator Heidi Heitkamp to Cher—neither of whom, unfortunately, turned out to be voting members of the DNC.

As I went with my fellow candidates through debate after debate, TV appearance after TV appearance, it became clear that my approach was hitting a nerve. People responded to the idea of a values-led message. They wanted us to compete in red and purple states, and to pay attention to local races. Most understood that a healthy strategy would involve emphasis both on racial justice and an economic message, not choosing one over the other. And to the extent that a candidacy from someone my age was itself a kind of message, the idea of mobilizing a new generation of voters and organizers, through fresh leadership and tactics, resonated strongly. As we engaged party faithful far from Washington, I could see in the faces of the audiences that a fifty-state strategy and a willingness to compete everywhere was already important to those on the ground.



IT WAS ALSO EVIDENT that the party itself was at a moment of truth, its future role unclear. In the suddenly antiquated twentieth century model, political parties had had a near-monopoly on information, access, and money. A volunteer list, a campaign finance account, or even just a way to get the word out about an event was difficult to build on your own. I thought of Butch Morgan back in South Bend, and the influence that he had once wielded from that landline phone on his desk at the party headquarters. But now online organizing and outside spending had eclipsed many of the functions of a traditional party organization—local and national alike. To be useful in the digital age, the DNC would have to figure out a new division of labor across party operations, campaigns, and causes.

An episode in Houston, during the heat of the race for chair, dramatized this humbling new reality for the party. We had come to Texas for one of four regional gatherings of DNC members, and the competitors for chair were at a reception after completing a forum (effectively a debate) before an audience of committee members and party activists. Earlier that day we had learned of President Trump’s travel ban on residents of certain Muslim countries, and word had begun to spread of a grassroots movement to protest the policy at airports around the country.

As appetizers and drinks circulated among candidates and party leaders in a hotel ballroom, my campaign staff learned that Texas was not immune to the grassroots pushback: a protest was getting under way at Houston Airport. Having spent the better part of the day advocating for a party leadership that could better engage with the grassroots, it now felt like I belonged there, with activists at the airport, not here at a reception with party functionaries, donors, and hors d’oeuvres.

A few minutes later, I was in a rented minivan with Chasten and several staff, racing to George Bush Intercontinental Airport, Terminal E. We were going as fast as we could—which, owing to pre–Super Bowl traffic, was not fast at all. I kept refreshing Facebook and Twitter to see how the protest was going, while also monitoring the news as accounts spread of an ACLU effort to stay the ban in court. After twenty minutes or so, we learned that Tom Perez had had the same idea, possibly after I tweeted my whereabouts, and soon another candidate, South Carolina Democratic Party Chair Jaime Harrison, was en route as well. All of us were literally racing to join those standing up for our values. But nothing was moving quickly on these logjammed roads.

As I looked out at the bumper-to-bumper traffic on the freeway, it hit me that we were enacting a highly metaphorical version of what was going on with the party at large. Here was a young mayor, a former Cabinet secretary, and a state party chairman, with their respective campaign entourages, all in hot pursuit—rushing into a comically slow-motion car chase, trying to catch up to a group of activists and citizens organized just hours earlier by a twenty-six-year-old restaurant server using social media.

Pete Buttigieg's books