Last week, twenty Democratic candidates for President debated in the course of two nights in Miami. Kamala Harris and Elizabeth Warren appeared to bolster their campaigns, with Harris, in particular, making headlines for her criticism of Joe Biden’s past opposition to school busing. Later in the week, Harris explicitly announced that she supports a return of school busing to ease segregation in education. This followed all of the candidates at Thursday’s debate coming out in favor of government-funded health care for undocumented immigrants, Elizabeth Warren supporting the decriminalization of border crossings, and Harris initially seconding calls from Warren and Bernie Sanders for the abolition of private health insurance. (Harris claimed that she misunderstood the question; earlier this year, she appeared to take several different positions on the issue.) Joe Biden’s unsteady performance, meanwhile, weakened the candidacy of the Party’s highest-profile moderate.

With President Trump and his team delighted by the Democrats’ leftward turn, a central question emerges: Will running on a more explicitly progressive platform energize the Democratic base, or will it cost the Party the 2020 election? To consider this question and others, I spoke by phone with Dave Wasserman, the U.S. House editor for the Cook Political Report and a contributor to NBC News. During our conversation, which has been edited for length and clarity, we also discussed whether voters are less ideological than people think they are, the ways in which the Electoral College presents a challenge to Democrats winning Presidential elections, and the true lesson of the 2018 midterms.

Do you think Democrats whose primary desire is to see Trump defeated should be concerned or excited that their party seems to be moving leftward?

I don’t think Democrats would be wise to run against Trump on a platform of completely open borders and abolishing private health insurance. There are limits. But, generally, the tiny sliver of voters in this country who are still persuadable are not highly ideological people. They are fundamentally anti-élite in nature, and they are looking for three characteristics in a candidate for President that don’t have much to do with left-versus-right. And those characteristics are authenticity, being a credible agent for change, and empathy. In other words, does this person understand my daily struggles? And a common thread between Obama and Trump was a common touch.

It’s all relative, but, whether it was having been a community organizer on the South Side of Chicago or a billionaire who ate K.F.C. and went to professional wrestling matches, it struck a chord with those voters.

Trump still got a lower percentage of the vote than Mitt Romney or John Kerry. Do you think there is a chance that we over-learn the lessons of a guy who got forty-six per cent?

Yes, but Democrats shouldn’t under-learn the lessons of Hillary Clinton’s failure. She was viewed not as an Arkansas Democrat but as a Chappaqua Democrat, by 2016. She ran a campaign that didn’t just fail in terms of targeting the right states but failed to drive an economic message. And “stronger together” and “Trump is unfit for office” were not substitutes for “here’s my plan to get the American heartland back to work.”

When you contrast Arkansas and Chappaqua, are you contrasting economics or culture? If you are arguing the latter, it seems like you could be arguing that “Massachusetts Democrat” could also be poisonous?

It’s more cultural in my opinion, but there is no question that Clinton could have talked about the economy more. The pitfalls in a potential Harris or Warren nomination are several. But the first one that comes to mind is the reinforcement of an image that the Democratic Party is dominated by coastal élitists, and, despite Warren’s Oklahoma roots and populist message, her career as an Ivy League academic is a liability, or would be a serious liability in a general-election campaign. In Harris’s case, Republicans would love to run against San Francisco, but, more than that, she hasn’t woven voters’ personal stories into her case for why she should be elected as often as some other candidates have. And that is one area where she probably has room to grow as a candidate.

It seems like you are saying freshness and authenticity are good, and we shouldn’t just be thinking about ideology, but there are various cultural markers which can be a problem, whether someone is centrist or left.

That’s correct, in my view. At this point in 2015, there was a widespread notion that the Republican candidate who wanted to build a wall and make Mexico pay for it was unelectable in a general election. That proved to be false. And we should be careful about making broad pronouncements about platform positions such as Medicare for All or an overhaul of ICE.

O.K., but it seems to me that there is a fundamental difference, which is that no Democrat is capable of winning with forty-six per cent of the vote, because of the Electoral College map. That may be because the system is unfair, but it seems like you can make an argument that Republicans have more leeway in how they can run.

That’s correct. The problem for Democrats is that they could still win five million more votes than Donald Trump and lose the Electoral College. The problem is that trends are benefitting Democrats in states that are not decisive in the Electoral College. Democrats are continuing to gain millions more votes in California. They could cut into Trump’s margin in Texas by eight hundred thousand and not be rewarded by a single electoral vote. Those trends are not as present in Wisconsin, Michigan, Pennsylvania. The question is: Can a more progressive candidate from a coastal state perform well in the middle of the country? And part of why Obama appealed in those [Midwestern] states was that he was a Midwestern candidate. He was someone who had experience going to fish fries in rural counties of Illinois, which, culturally and economically, are a lot like the parts of Wisconsin and Michigan and Iowa where Democrats’ fortunes have fallen recently.

So we shouldn’t assume we know how this will work—I certainly don’t—but the Democratic bar is simply higher.

That’s correct. I believe too much of the media in Washington, D.C., is viewing candidates’ chances against Trump through a left-versus-right spectrum, or a sliding scale, in which if they nominate Biden they can win middle America, but if they nominate someone too far left they will risk alienating those voters. I don’t view it that way. The reason that, in my opinion, Biden is vulnerable—perhaps more vulnerable than other Democrats in the race [against] Trump—is that I have watched congressional races for the last twelve years, and, over and over again, I have seen candidates with long paper trails and voting records get picked apart for every comment they made twenty or thirty years ago. And that’s what is happening at the moment.

The Biden people would probably say they are being picked apart for things that aren’t going to hurt him if he makes it to a general election, though, right?