If you want to know how far Pete Buttigieg has come, just look to an event back in February, when he showed up to speak with Democrats in a suburb just outside of Des Moines, Iowa. There were maybe a few dozen people in the room. It felt a little bit like a book signing. When the woman introducing him mentions that Buttigieg won 80 percent of the vote back in South Bend, Indiana, during his last mayoral election, he makes this embarrassed smile. Like, “Who, me?” The Washington Post called him “the most interesting mayor you’ve never heard of.”

Flash forward to a couple of weeks ago, to an Iowa event called the Liberty and Justice Dinner. But now, the audience is holding thundersticks. They’re wearing bracelets that light up in time with Mayor Pete’s walk-on music. It takes Buttigieg a full minute to just get a word in edgewise.

Tonight, as the Democratic candidates take the stage for yet another debate, Pete Buttigieg will stand at his podium as the Iowa front-runner. He has come a long way. So how did the 37-year-old mayor of South Bend get here? And how will his competitors try to knock him off his game at the debate?

To answer those questions and understand Buttigieg’s rise in Iowa, I spoke to Adam Wren on Wednesday’s episode of What Next. Wren, a reporter for Politico Magazine and the Indianapolis Monthly who has been writing about Buttigieg since he was just a local mayor with big ambitions, has been riding around on Buttigieg’s campaign bus. Below is an edited transcript of our conversation.

Mary Harris: The last time there was a Democratic debate, I spoke to this political analyst, Amy Walter, and she said, “Listen, you should just watch Mayor Pete.” It feels like it’s turned out to be really prescient now, like a month later.

Adam Wren: Yeah. You know, when you look back at the sum total of Buttigieg’s debate performances, it’s almost like he’s sort of a distance runner. In the last debate that we saw, he sort of came out of nowhere. It was almost like a different Pete Buttigieg, where he took things up a level and really started to draw attention to himself by contrasting with fellow candidates like Sen. Elizabeth Warren on “Medicare for All” and contrasting his youth with former Vice President Joe Biden. So as we enter into tonight’s debate, it’ll be really fascinating to see which Mayor Pete shows up. Are we going to see a pugilistic Pete, like we saw last time? Or given his rise in Iowa, are we going to see him pivot to this sort of statesmanlike figure, where he’s sort of above the fray, above the competition? I think both of those possibilities could pan out.

He’s a little cocky, too. I mean he went on a TV show and basically said, “I think this is a two-way race between me and Elizabeth Warren at this point,” which is saying something given that there are two dozen people in this race.

You know, some people read his comments like that, but having spent time with him and sort of becoming a student of his political career, I think I read it as more of almost a consultant sort of stepping outside of himself, and stepping outside of the race, and sort of analyzing where things were going a month or two out. But certainly his competitors and detractors saw this as something that was cocky, and the net effect of it was, yes, somewhat hubris-filled.

Can we talk about how Buttigieg got to this place? Because looking back, he seems to have had this strategy that seems kind of brilliant. He hired a media expert, this woman Lis Smith, and the idea in the early part of this year was just “say no to no one.” He would show up on whatever podcast wanted him and basically teach everyone how to pronounce his name and explain who he was.

That’s right. An example of that is in January, right after he launched his exploratory committee, he actually went on a local podcast here in Indianapolis called Pete the Planner, which is a personal financial planning podcast for people who want to save for retirement or are wondering how big their mortgage should be. He called in and talked about student loan debt and how he approached his personal finances. So yes, he would say no to no one.

As we got closer to April, he had a town hall in Austin with CNN and sort of had this breakout moment where he criticized fellow Hoosier Vice President Mike Pence in a way that really elevated his platform. And then from there, he launches in April and sort of skyrockets in the polls and in fundraising. He sort of blew a lot of his competitors out of the water with his second-quarter fundraising results, and he just kept going up and up.

It feels like part of what happened was there was this strategy to get him on any and every outlet that would have him, so all of a sudden, Mayor Pete is everywhere, you’re hearing his name, people are listening. That brings in donors, and then that seems to make the snowball roll even faster.

Yeah. It’s like a flywheel. It’s like a self-perpetuating cycle of positive press, which leads to fundraising, which leads to escalation in the polls. It’s fascinating because a year ago this month, I could go to South Bend and sit down at a local café with the mayor and talk with him with sort of no one noticing. Now he’s followed by a dozen national reporters, he has his own private security. It’s a sea change that has happened in just over a year.

Is it fair to say, in terms of the donors, that he’s going after big-ticket Democratic insiders, who Elizabeth Warren and Bernie Sanders might be avoiding?

I think that’s part of it. He’s doing a lot of grassroots events [too], so it’s sort of an all-of-the-above strategy. You know, he does have an appeal in corporate America, to sort of centrist Democrats who are not happy with the Trump presidency and see in Pete Buttigieg someone who is thoughtful, socially progressive, but in some ways fiscally conservative. He does talk about the national debt and was asked about it on this swing through Iowa. He sees it as sort of a generational problem, so there is some corporate appeal there that results in fundraising.

So this surge that Buttigieg has been having in Iowa—it’s important to Democrats for a lot of reasons, but mostly because for the last few decades, most of the time, the Democratic nominee for president has won either Iowa or New Hampshire or both.

That’s correct. So when you go back to the week before the Liberty and Justice Dinner in Des Moines, people on his campaign who had worked for President Obama’s campaign were sort of building it up as a sequel to what Obama did when he was in sort of a dogfight with Hillary Clinton in 2008, leading up into the Iowa caucuses in January. He really used that speech as a way to sort of leapfrog her and eventually win Iowa.

At the time, back in 2008, President Obama, the first black president, was struggling with voters of color in places like South Carolina, but once he won the Iowa caucuses, that really sent a message to people in New Hampshire and South Carolina that if he could win in white, rural Iowa, that he could win maybe anywhere in the country. And so Pete Buttigieg’s advisers, before the Liberty and Justice speech, were actually sort of making a similar case that if he can do well in Iowa, he’ll send a message to African American voters in places like South Carolina, and they might give him a second look.

Buttigieg’s campaign needs that second look from black voters, because that is where the mayor’s poll numbers are remarkably low. They have been for months. He’s been criticized for how he deals with race by South Bend activists, political pundits, members of the Congressional Black Caucus. What’s the campaign doing about this?

He’s responding in a few different ways. Earlier this year, he actually named an Indiana state director for his campaign, which I think a lot of people saw as presumptuous because Indiana doesn’t vote until May, and this Indiana state director that he named was Arielle Brandy, who is an African American here in Indiana, well respected, well known in political circles. He named her as his Indiana state director, and yet just this week she has been traveling to Georgia, will be traveling to places like South Carolina, to more or less vouch for the mayor. She lives in South Bend, she’s a political player there with ties to the NAACP, and she will be someone who the campaign uses as a surrogate—even though she’s an Indiana state director—in a number of states like South Carolina.

They’ve also identified African Americans who live in South Bend and are favorable to the mayor to sort of be these validators on social media. And one has been tasked with opening up a new South Bend office that’s designed to be the public-facing version of a campaign office and allow volunteers to come in from South Bend who support the mayor and actually make calls to early states, in places like Iowa and New Hampshire and South Carolina, on his behalf.

It seems to me like when the mayor is called out on race, he has a couple of different things that he does. One of the things that he does is he brings up his identity as a gay man. Can you talk a little bit about how that conversation goes, when you’ve seen it happen?

Yeah, that’s correct. He’s used this part of his story not only with African Americans, but with people, for example at a town hall in Iowa, who have disabilities. He often says that all of us, in one way or another, have brushed up this crisis of belonging, whether we’re a minority, whether we’re gay or we have a disability. He says, “All of us in different ways have been led to question whether we belong, and I know what it is to look up on the news and see your rights up for debate.” That’s sort of the way that he talks to communities who might have “other” status, and he tries to identify with them in that way.

The other thing he tries to do is he likes to pivot to his plan. He has this plan called the “Douglass Plan,” which he released in June, and it’s a really multifaceted approach to dealing with structural racism. But even the rollout of that plan has been really fraught, even in the last week.

Yeah, that’s correct. So one of the things they did to roll out this plan was announce the endorsement of roughly 400 South Carolinians, both African American and white South Carolinians. As that announcement rolled out, many people who were on the list received calls from neighbors and friends or other elected officials, and they said, “We didn’t realize you were endorsing Pete Buttigieg.” And they would say, “Well, we’re not, actually. What do you mean?” And it would turn out their names would be on this list without what they felt was their consent.

Not only that happened, but also when they had a contractor help build out their website, the contractor used a stock photo from Kenya on the Douglass Plan page of their website to market this, which is incredibly tone-deaf.

It’s interesting to hear you talk about this because it sounds like turning the key on an engine, trying to get it to catch. Like, trying again and again to try to get this plan to break through and get the attention of the people you want to signal to.

That’s right. I think that’s an apt metaphor. You know, what the Buttigieg campaign would say is that, look, this is someone who has not been running for office for three decades, like former Vice President Joe Biden, who isn’t really well known nationally, and when it comes to a group of voters who might be skeptical, he’s going to naturally have to work hard and struggle for their vote. And yet, time and again, it seems like he struggles to get that engine to kick.

There was some coverage of Pete Buttigieg from back in September: It was an article on Politico, and the author straight-out said that Buttigieg has no strong and unique governing vision. It stood out because I felt like, at the root of it, that’s a little bit what the African American community is saying.

So this is an article by my colleague at Politico Magazine, Bill Scher, and I think what he’s getting at there is that it’s difficult when you’re the mayor of a town like South Bend, as far as your governing vision is concerned, because your job is to plow the streets of snow, and to make sure the sewers work, and to make sure the proverbial trains run on time. So Buttigieg constantly throughout this year is navigating both the blessings and the curses of being a mayor.

He gets the blessings from being a mayor when he talks about nonpartisan or bipartisan approaches to governing, solutions-based policy. But he gets all of the curses of being a mayor when it comes to his policy, because a mayor is in some ways not ideological when it comes to plowing the streets or making sure the parking meters work. So, yes, he gets the optics of being a mayor who’s out using a snowblower to clear the streets of snow, but he also has to deal with the limitations of the power of his own office that he holds presently.

I wonder if you’d agree with your colleague and say, “Yeah, there’s no overarching vision.” Or whether you’d say: “Listen, Mayor Pete is figuring it out. That’s not really what his job was before.”

I think that my colleague makes a really compelling point. I think Buttigieg occupies this place in the field right now where he is trying to be the Goldilocks candidate. Not too progressive, not too conservative. And he’s really benefiting from that right now. He smartly positioned himself as sort of an understudy to Joe Biden, in the event that Biden didn’t really catch on with voters.

So when you saw this poll come out from the Des Moines Register on Saturday night, you saw Biden plummet to third place and Buttigieg occupy his spot. I think he’s pulled off, up until this point, that Goldilocks candidate, but the drawback on that is that it doesn’t seem like he has defined commitments or values like, say, a Sen. Elizabeth Warren does.

So while Elizabeth Warren is rolling around Iowa in a bus that says, “Honk if you want big structural change,” the answer to that may be, “No, thanks.”

That’s right. And if Buttigieg was driving around the same bus, it would be, “I’m going to take us forward, not left or right.”

OK, so that sets us up for tonight. Pete Buttigieg is going to walk onto this debate stage. How do you think the other candidates are going to respond to him?

Well, if the last few days leading up to tonight have been any indication, it could be a slugfest. We’ve seen candidates like California Sen. Kamala Harris say that she never had to acquire ways to talk about the black struggle because she was born with them. We’ve seen candidates like Julián Castro question the mayor’s qualifications to lead the country. So if that all kind of comes together on the debate stage tonight, it could be quite the conflagration.

You’ve said that Buttigieg’s campaign is relishing this moment. What do you mean by that?

Well, when you go back to January or February, many people, including national news commentators, couldn’t pronounce this candidate’s last name or sort of referred to him in a derisive way. And now here we are, and he’s leading, according to two recent polls, the first caucus state. They feel like they’ve gotten the job done, which is to bring to Pete Buttigieg as many voters and as many eyeballs, as many ears as possible. They feel like that’s a success for them. And so now that they’re getting attacked, it’s like, “Look what we have done. Our plan all along has worked, and here’s the mayor of the fourth largest city in Indiana who is potentially becoming, if not the front-runner in Iowa, the front-runner nationwide.”

Listen to the full episode of What Next here: