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Donald Trumps 2016 electoral college victory was, in many ways, epitomized by his stunning win in Wisconsin. Hillary Clintons failure to visit the state during the general election campaign took most of the blame, but her weak Badger State ground game was probably more crippling. Ben Wikler has spent the past 18 months trying to fix that problem. An activist since his high school days in Madison, Wikler attended Harvard; helped former Minnesota senator Al Franken write two books and produced his radio show; launched his own podcast, The Flaming Sword of Justice; then became MoveOns Washington directorall good preparation for being elected last year, at 38, as chairman of Wisconsins Democratic Party. He has overseen traditional tactics like deploying thousands of volunteers, but also novel ones, including cast members of The Princess Bride, Parks and Recreation, and Veep reuniting virtually to raise money for the state party. Vanity Fairs Chris Smith spoke with Wikler about the 2020 endgame in a crucial battleground state.

Vanity Fair: Were talking exactly two weeks before Election Day. How are you feeling?

Ben Wikler: Its like being on a roller coaster in the middle of an earthquake. Theres not a lot of sleep happening.

Well, you have three children under the age of nine, so that should be familiar. But what about the presidential campaign in Wisconsin?

The level of grassroots Democratic energy feels like 2008 and the Obama campaign. The level of Trumpian malevolence and willingness to smash every rule feels like 2016 on steroids. And those two realities are about to smash into each other.

The most recent Marquette poll had Joe Biden up by five points. Do you believe it?

The most hopeful thing about the polling in Wisconsin is that it has been remarkably steady for months and months: Biden has been up between four and six points. I think every Democrat in the state remembers that Hillary Clinton was six and a half points up going into Election Day in 2016 and lost by less than one percentage point. So you have to treat what looks like a solid lead as a knifes edge. As a jump ball. Its neck and neck. Is that a triple metaphor?

Youve talked about how the surest way to win Wisconsin is for a presidential candidate to visit multiple times and meet voters. Biden and Kamala Harris held small events in Kenosha after the police shooting of Jacob Blake, and in late September, Biden stopped at a foundry in Manitowoc but spoke to maybe a dozen people. Last Saturday, Trump held a rally in Janesville that drew thousands. Is the pandemic creating the same dynamic that lost the state for Democrats four years ago?

The fact that Joe Biden and Kamala Harris are not holding super-spreader events is a way of communicating that they mean what they say about bringing this pandemic under control. Were holding virtual events constantly with the nominees, with surrogates, with activists and leaders of all kinds. Those help too. We have had massive virtual phone banks. We have text banks. We have friend banks where people go through their own contacts. We have planes flying over Milwaukee with banners. We have mail pouring into peoples mailboxes. We have digital ads on every screen someone might open. The Biden team is outspending the Trump campaign more than two to one on TV ads. And were actually going to have sound trucks in major cities in the final stretch.

Trump is reinforcing with every one of his rallies that he doesnt actually care about the millions and millions of families who are grieving or are fundamentally reshaping their lives to avoid endangering their communities.Hes doubling down on the exact strategy thats causing him to lose.

Wisconsins Democratic governor, Tony Evers, tried to delay the states April primary because of the pandemic, but the Republican-majority legislature and the courts refused. That produced something both heroic and infuriating: epically long lines of voters. Will the waits be better or worse on November 3?

The mechanics are vastly improved because we had the brutal lesson of the spring. Milwaukee, which had 180 polling places in previous elections, shrank down to five because so many poll workers dropped out in April due to the coronavirus. So going into the fall, we got phone banks going six nights a week to recruit poll workers. The plan currently is that 173 precincts will be open in Milwaukee, despite a COVID-19 outbreak now thats worse than the one we had in the spring.

Another one of your organizing pushes has been aimed at holding down Trumps margins in rural, red counties. Hows that going?

There are three pillars holding up an electoral victory in Wisconsin: cities, suburbs, and rural areas. Trump is gaining no ground in cities, and hes underperforming in suburbs so badly that his only path is to blow the roof out in rural areas. Unluckily for Trump, weve been organizing in rural Wisconsin intensively for the last three and a half years. In every election during this period, we are closing margins rather than letting Trump grow them. There was a lot of talk in 2016 about the shy Trump voter who wasnt necessarily talking to pollsters. In a lot of the reddest places in Wisconsin, there has been a shy-Democrat phenomenon. Driving around Wisconsin in 2016, it was just a sea of Trump signs. Now there are Biden signs on lawns, on the sides of roads, on the sides of barns. Handmade murals and flags.People are discovering there are a lot more Democrats around than they thought. For folks who might have been feeling hopeless, its actually giving them permission to think that we can really win. Ive been speaking to rural Democratic county party meetings, and they have been marveling at all these people they didnt know were Democrats.

That all sounds encouraging. Yet Wisconsin Republicans recently won a federal appeals court ruling that will restrict the counting of mail-in ballots to those physically received by November 3.

Weve appealed to the U.S. Supreme Court, which just upheld a ruling allowing Pennsylvania to count ballots that come in after Election Day. But were organizing as if the existing rules are what will prevail.

Four years ago Koch money helped Trump in Wisconsin. Is that spending happening again?

Other conservative groups are doing their dark money thing. Yet if you add together what the dark money groups and the Trump campaign are doing, its still far short of what the Biden campaign alone is spending. Still, its very clear that the whole right-wing infrastructure has coalesced around Trump in a way that it actually didnt in 2016, when people like Charlie Sykes, the radio host in Milwaukee, were against Trump and others sat it out. So you saw declining turnout in places like Waukesha. This time, if youre a Republican in Wisconsin, youre supporting Trump.

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Wisconsin Democrats Are Organizing Like Mad. Will It Be Enough? - Vanity Fair