His entry into the 2020 race back in January seemed like a lark. As the 37-year-old mayor of South Bend, Indiana, Pete Buttigieg had only won about 20,000 votes in his entire career in electoral politics. The idea that a small-city mayor could hack it in a field that would eventually swell to include Elizabeth Warren, Bernie Sanders, and Joe Biden seemed remote, in spite of his eloquence, stacked resume, and soaring promises of generational change. Even surges in the spring and summer didn’t erase skepticism about his staying power, especially as his forays into the upper tier of candidates invited scrutiny into his record back home.

But now, three months out from the first contest of the Democratic primary and a year out from the general election, Buttigieg is still behind Biden, Warren, and Sanders nationally, but has overtaken the former vice president in Iowa, where a big win in February’s caucus could catapult him to the front of the field. Indeed, Buttigieg has gone from something of a novelty to a real Iowa contender, sitting third in the state behind Sanders and Warren. As of now, it seems clear that Buttigieg will be competitive in the Hawkeye State, which is arguably more important than ever in terms of the Democratic primary. What’s less clear is if he can find success beyond that with voters, both in the Democratic primary and in a general election against Donald Trump.

Buttigieg has capitalized on several missteps by Biden, challenging the former vice president’s claim to the center lane. Where Warren, who has herself surged to become one of the frontrunners, has made her mark by putting forth a bold progressive agenda, Buttigieg has run on a broadly centrist platform and increasingly focused his rhetoric on bridging partisan divides and healing the Trump era’s political wounds. “We will fight when we must fight,” he said in Iowa during a whirlwind trip through the state, drawing large, enthusiastic crowds along the way. “But I will never allow us to get so wrapped up in the fighting that we start to think fighting is the point. The point is what lies on the other side of the fight.”

That such rhetoric recalls Barack Obama is no accident; Buttigieg has sought to present himself as the heir apparent to the former president’s legacy, modeling his own campaign on the one Obama ran in 2008. “The idea of hope may have gone out of style a little bit,” Buttigieg said at a recent campaign event in Des Moines. “But when I look at you, I see it is not out of style.” As the New York Times’ Astead W. Herndon pointed out Monday, however, there are crucial differences between the two candidacies. While each represents a potential first—Obama was the first black major party nominee; Buttigieg is vying to become the first openly gay nominee—Obama proved to be a masterful coalition builder. Buttigieg, meanwhile, has struggled to make inroads with black voters. Some, like Rep. Jim Clyburn of the Congressional Black Caucus, have suggested his sexual orientation could be a factor. Others, including Kamala Harris, have dismissed that notion. “To label one community in particular as being burdened by this bias as compared to others is misinformed,” she said Monday.

Buttigieg has struggled to appeal to minority voters as the race has worn on, a vulnerability some of his Democratic opponents have sought to exploit. Buttigieg has a “bad track record with African Americans on the issues,” Julian Castro said at a campaign event Sunday. “Anyone who thinks this is a two-person race doesn’t know anything about the Black and Latino communities,” Castro added, referring to remarks Buttigieg had made suggesting the nomination would be a toss-up between himself and Warren. Buttigieg retorted that “the black voters that know me best have returned me to office and supported me more the second time than the first,” but according to a Politico analysis of election numbers, Buttigieg’s support among black voters in South Bend weakened from his first race to his second.