The Shocking Upset That Shows How Democrats Can Crush Trump

Lloyd Grove
·6 mins read
Photo Illustration by Kristen Hazzard/The Daily Beast / Photo Getty
Photo Illustration by Kristen Hazzard/The Daily Beast / Photo Getty

On Nov. 8, 2016, Donald Trump upset Hillary Clinton in the critical battleground state of Wisconsin—and won its 10 electoral votes—by a razor-thin margin of 22,748 out of the 2,787,820 ballots that were counted.

Along with Trump’s narrow victories in Michigan (by 10,704 votes) and Pennsylvania (by 44,292), Wisconsin enabled the fresh hell that Democrats, immigrants, women, minorities—and that diminishing population of principled Republicans—have been enduring every day for the past three years and seven months.

Dress Rehearsal—a documentary short that, absent a viral plague, would have debuted next week on the night of Joe Biden’s acceptance speech before thousands of cheering delegates in Milwaukee’s Fiserv Forum—offers Trump’s opponents a rosy scenario for preventing a recurrence of such a catastrophe on Tuesday, Nov. 3.

Director David Modigliani’s 17-minute film—which instead will receive its premiere online on the same Thursday night as Biden’s oration, the night after California Sen. Kamala Harris is scheduled to accept the vice presidential nomination during an all-virtual Democratic National Convention—chronicles how Wisconsin Democrats deployed digital technology and “relational organizing technology” (a fancy term for friends talking to friends) to triumph over the lethal COVID-19 pandemic and the GOP’s relentless campaign to suppress the vote.

Modigliani, for his part, claimed not to be disappointed that he will have to imagine the applause his premiere might otherwise receive.

“While that [a Fiserv Forum premiere] would feel good, I actually think it’s kind of perfect that folks are going to watch this film on their laptops, on their phones, through the very digital devices that we need them to employ to get involved in this election,” he told The Daily Beast. “As they watch through their laptop screens, they will see organizers on their laptops and phones executing a new strategy in this digital space.”

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Dress Rehearsal was commissioned by Higher Ground Labs, a Democratic-oriented venture capital firm marrying politics and technology, whose investors (to the tune of $15 million) include Silicon Valley billionaires like Reid Hoffman, Ron Conway and Chris Sacca. (Two other Democratic firms, ACRONYM and Arena, also funded the film.) The for-profit Higher Ground Labs is separate from Barack and Michelle Obama’s Higher Ground Productions.

“We had the name first—we should sue,” joked Labs co-founder Shomik Dutta, an executive producer of Dress Rehearsal.

“Part of the importance of the film is the power of the symbolism,” Dutta, a former Obama White House political aide and campaign fundraiser, told The Daily Beast. “This tiny band of Democratic activists and organizers, trapped in their homes in the middle of a pandemic, helpless and buffeted by all these onerous and draconian rules passed by Republican legislators to stop voting and stop democracy in action—they overcame this by reaching out to each other.”

The Democrats’ efforts in Wisconsin produced a massive turnout for a down-ballot contest and a shocking upset this past April 7 in the State Supreme Court race in which the liberal challenger, Circuit Court Judge Jill Karofsky, beat the conservative favorite, Trump-endorsed incumbent Justice Daniel Kelly, in a crushing landslide.

Karokfsy donned her justice’s robes this month for a 10-year term.

“I remember watching this race closely in April and frankly feeling fairly dejected on election day after witnessing the myriad ways that Republicans did everything they could to suppress the vote in the middle of a pandemic,” President Obama’s former chief speechwriter Jon Favreau, who appears in the documentary, told The Daily Beast.

“In addition to that, the pandemic itself upended the best-laid plans of Democrats in Wisconsin to launch this massive organizing campaign. They were going to be door-knocking for weeks on end. And as we got closer to election day, I thought, ugh, this is going to be a really hard race to win.”

Favreau, among the Obama loyalists who founded Crooked Media, the home of Pod Save America and its activist subsidiary Vote Save America—the websites that will host Dress Rehearsal‘s Aug. 20 premiere—continued: “But the Democrats turned on a dime to figure out how to organize digitally, and the Republican efforts to suppress the vote engendered such a backlash from people who were going to show up anyway and said, ‘You can’t tell me I can’t vote! Absolutely I’m gonna vote!’

“Then it suddenly became one of the more inspiring stories in 2020 of what could happen in November if we’re able to get smart and figure out how to organize in a pandemic-ridden country where Republicans are doing everything they can to stop people from voting.”

Unlike Modigliani’s previous political documentaries—2019’s Running with Beto (a contemporaneous chronicle of Texas Rep. Beto O’Rourke’s failed Senate race against wingnut incumbent Ted Cruz) and 2008’s Crawford (about the life-changing impact on a tiny Texas town of President George W. Bush’s purchase of a nearby ranch)—the filmmaker had to construct the story, in all its tension and drama, after the outcome was already known.

Arriving on the ground in mid-June, more than two months after the balloting, Modigliani licensed some real-time footage taken by others on election day, but mostly relied on retrospective interviews with around 50 activists, operatives, volunteers and voters. Because of the pandemic, the crew wore masks, socially-distanced and filmed outdoors, while coaching interview subjects how to clip on their own microphones.

Among the dozen folks who made the final cut are everyone from paid Milwaukee canvasser Keviea Guiden (a former gang member-turned-community organizer who took the job because “I’m a little overweight so I was like, OK, maybe I’ll get a little exercise and lose a few pounds”) to Wisconsin Democratic Party Chairman Ben Wikler who, along with executive director Nellie Sires, orchestrated the digital campaign amid the pandemic to show millions of registered voters across the state how to apply for and mail in absentee ballots.

“This new guy, who’s running the Democratic Party here—Wikler—is a rather dramatic upgrade from his predecessors,” said Charlie Sykes, a longtime Wisconsin conservative Republican and current Never-Trumper who is editor-at-large for Bill Kristol’s The Bulwark. The Democrats’ victory in the kind of low-turnout election usually won by Republicans “was a shock and nobody really saw it coming,” Sykes told The Daily Beast.

“It’s kind of a reversal of fortunes,” he added. “People forget that Reince Priebus was the head of the Republican Party here in Wisconsin, and he was a very effective chairman. He built this tremendous get-out-the-vote machine that helped propel [former governor] Scott Walker and [Sen.] Ron Johnson and others. The last ten years has been marked by the dominance of the Republicans in the get-out-the-vote effort. And this year people were surprised that the Democrats finally got their act together.”

And the implications for Nov. 3?

“I think November 3rd is in a class all by itself,” Sykes said. “But if this is an indication that the Democrats have their act together, and the Democratic base is extremely enthusiastic, then that’s very bad news for Donald Trump in Wisconsin.”

Read more at The Daily Beast.

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