After two years of speculation about which of them is best suited to bring the Trump era to a merciful end in 2020, Democratic politicians who have been spending their free time forming exploratory committees, soliciting donations, giving inspiring speeches, and hanging out in Iowa diners are at last announcing formal bids to become the next president of the United States. Over the next few weeks, we'll take a look at each of the front-runners: Who are they? What do they stand for? And in order to have a shot at winning the nomination they seek, what tough questions will they have to answer first?

Previously, we looked at Kamala Harris, Bernie Sanders, Elizabeth Warren, Cory Booker, Joe Biden, and Beto O’Rourke. Next up: South Bend, Indiana mayor Pete Buttigieg.

Why is the mayor of a mid-sized Midwestern city running for president?

With apologies to O’Rourke, a three-term congressman who lost a Senate race and is now running for President of the United States, Buttigieg—known around South Bend and/or the Internet as “Mayor Pete”—is the most obvious answer to the question, “Which serious Democratic hopeful is perhaps furthest out over his proverbial skis?”

Since graduating from Harvard College in 2004, Buttigieg (that’s “BOOT-a-judge,” which is why “Mayor Pete” comes in so handy) has worked on a handful of unsuccessful campaigns in Indiana, studied at Oxford on a Rhodes Scholarship, and spent stretches at two consulting firms, including three years at global behemoth McKinsey and Company. In 2011, he was elected mayor of his hometown, and won a second term in 2015; a Naval reservist, he spent seven months in Afghanistan as an intelligence officer in 2014. These are extremely impressive credentials! Compared to the senators and governors and former vice presidents in the running, though, Buttigieg’s résumé reads like it accidentally got cut off after the first few lines.

The reason he isn’t seeking a job that somewhere between “medium-sized-city-mayor” and “President of the United States” is probably the same one that nudged Beto into the race: Buttigieg has the misfortune of being a bright Democratic star in a solidly-Republican state, which leaves him with few appealing prospects for seeking higher office. South Bend sits squarely in a red congressional district once represented in Washington by Mike Pence. Indiana hasn’t elected a Democratic governor since 2000. The state does not have a Senate election until 2022, and neither the 2016 nor 2018 contests were particularly close. Recently-ousted Democratic senator Joe Donnelly can credit his surprise 2012 win mostly to the fact that his opponent, Richard Mourdock, opined during the campaign that pregnancies caused by rape are “something that God intended.” (Mourdock still lost by fewer than six points.)

Perhaps Buttigieg surveyed his options and decided that if you’re bound to be a long shot in your next election, you might as well get ambitious about it. But deciding instead to mount a Senate or gubernatorial bid in the next few years—even a Beto-esque spirited losing effort—would do wonders for his national profile. (Buttigieg’s unsuccessful bid to chair the DNC in 2017, for example, did exactly that.) His challenge in this contest will be to articulate why he is so well-suited for the White House right now.

Can a millennial make a viable candidate?

“It’s time for a new generation of American leadership,” reads the splash page on Buttigieg’s web site. The 37-year-old has been widely touted as the first millennial major-party presidential candidate, as recently exhibited by his made-for-virality participation in the most online of all online debates: Is a hot dog a sandwich? (His ruling, for the record, is no.)