It was roughly 16 hours after Andrew Gillum had all but labeled Ron DeSantis a racist, and his audience was all smiles. Before Gillum, the Democratic nominee for Florida governor, even arrived on campus at Florida Memorial University in Miami Gardens for his Thursday afternoon rally, speaker after speaker in the historically black university’s auditorium approvingly recounted his line from the previous night: “My grandmother used to say, ‘A hit dog will holler,’ and it hollered through this room,” Gillum, the 39-year-old, progressive, African-American mayor of Tallahassee had said, mere feet away from his Republican opponent, the 40-year-old former congressman. “Mr. DeSantis has spoken. First of all, he’s got neo-Nazis helping him out in the state. He has spoken at racist conferences. He accepted a contribution, and would not return it, from someone who referred to the former president of the United States as a ‘Muslim n—.’ When asked to return that money, he said ‘No.’ He’s using that money to now fund negative ads. Now, I’m not calling Mr. DeSantis a racist. I’m simply saying the racists believe he’s a racist.”
When Gillum eventually arrived for the rally, walking onstage alongside civil-rights hero turned congressman John Lewis to encourage the crowd to vote early, he smiled, looked out at the audience, and asked if they had watched the debate. They had.
“We have to be honest. And — guess what? — people will reward you by your honesty,” Gillum told me backstage, just before greeting the gathered students. “I think we, probably for too long, have felt that we have to act a certain way, talk a certain way, come from a certain pedigree, and I think that mold is broken. And I think it’s broken permanently.” Minutes earlier, Gillum had wrapped up another rally with Florida senator Bill Nelson, who told his audience they’d be singing “Happy Days Are Here Again” after Election Day. At roughly the same time, the sound system turned on at Gillum’s FMU event, his second of the day, and it began blasting Childish Gambino’s “This Is America.”
It wasn’t always clear that Gillum’s attempt to become Florida’s first Democratic governor in nearly two decades would lean so far outside the traditional (boring) lines. In the days after his shock August primary win, Washington pundits proclaimed the race both a proxy battle between Bernie Sanders’s leftism and straightforward Trumpism, and, therefore, a preview of a possible 2020 presidential matchup. Instead, the campaign has highlighted the results of Democrats’ attempt to craft a modern identity in an environment where all politics is national. And in Gillum, Florida Democrats have recalculated what counts as “electable” after losing five straight gubernatorial races with relatively centrist white nominees — a bet on boldness that runs parallel to their case that DeSantis is too extreme for traditional Republican voters.
Florida’s race isn’t the only one with this kind of dynamic: It’s echoed in Georgia’s gubernatorial contest, where recent accusations of intentional voter suppression have shone a national spotlight on the campaign between Secretary of State Brian Kemp — a Republican strongly allied with Trump, whose early ads included one spot where he points a gun at a young man interested in dating his daughter, and another where he drives a pickup truck speaking of rounding up “criminal illegals” — and former statehouse minority leader Stacey Abrams, a longtime Democratic rising star who would be the nation’s first black woman governor if her attempt to turn out previously disaffected voters, largely African-Americans, works.
Yet it’s Gillum, and his Florida contest, who’s attracted the attention of not only the national press, but both parties’ leading strategists and donors, who’re looking for clues about what could work in the most important battleground state in presidential races, ahead of 2020. (Liberal billionaires George Soros, Tom Steyer, and Michael Bloomberg have all invested in Gillum, while leading GOP tycoons Sheldon Adelson, Ken Griffin, and Dick Uihlein have funded pro-DeSantis efforts.) “The possible foreshadowing of the 2020 presidential race is a very liberal candidate running in a purple state or states where Democrats have long said were going to turn blue,” said Republican pollster Bill McInturff, pointing to the two gubernatorial races and Texas’s Senate contest as “the three campaigns that might tell us something about where the country is headed.”
The focus makes sense: Control of Florida could significantly alter both parties’ planned path to 270 electoral votes in 2020, and while Gillum has led DeSantis narrowly in most polls, the race is generally considered a toss-up. If Gillum wins, Republicans will need to go back to the drawing board to design a kind of candidacy that’s acceptable to both Trump and his voters and moderates. If DeSantis prevails, Democrats will likely second-guess their choice to stray from their usual plan of attack in Florida.
Gillum’s path to victory relies in part on reshaping an electorate that broke for Trump in 2016 after voting for Obama twice, like Democrats are eager to do around the country. While DeSantis is aiming to replicate the president’s strength in a state he won with high white turnout, Gillum has veered away from the traditional Democratic path to victory. He’s still hoping to run up the score among Latino voters, but after a primary win fueled by unexpectedly large margins among African-Americans, in Jacksonville’s Duval County, and on college campuses, Gillum’s now spending more resources on pumping up turnout among black and young voters than his party has before — especially in 2016, when Hillary Clinton underperformed with both groups. The fact that he would be Florida’s first African-American governor should help, explained Meg Ansara, a Democratic strategist who directed Clinton’s battleground-states operation: The fact is “going to motivate large numbers of people of color, progressives, and young people to vote in this election who might not ordinarily vote in a non-presidential race.”
But Gillum is also the most progressive statewide candidate nominated by Florida Democrats in recent memory, testing the left bound of acceptability in the ultimate purple state, just as DeSantis is the most Trumpian.
The morning after the primary, DeSantis said Florida voters shouldn’t “monkey this up” by electing Gillum, and the Florida GOP’s ads have since warned Spanish speakers of the “MISERIA” of socialism, tying Gillum to Sanders. DeSantis rose to prominence in the first place only after gaining Trump’s approval through his repeated Fox News appearances last year, and he even ran a tongue-in-cheek ad featuring himself building a Trump-style wall of building blocks with his toddler daughter and reading The Art of the Deal to his baby son. Gillum, meanwhile, campaigned in the primary on a single-payer health-care system, abolishing ICE, and impeaching Trump. “Our voters are going to stay home if they have to choose between someone pretending to be a Republican and someone who is a real Republican,” he said at a rally with Sanders in August.
It’s all a bet that, in the age of Trump, Democrats have little room for wishy-washiness, even in the closest states. Still, it’s not always an entirely comfortable fit: Gillum has at times tacked to the middle, raising money with both Clinton and Bloomberg in recent weeks, and he himself is a longtime player in the state capital of Tallahassee — DeSantis is now on the attack over gifts that Gillum appears to have received inappropriately as mayor — and has not always governed his city as an ardent progressive. “If you look at his time as mayor, dude was a very practical, pragmatic mayor. He was not the more liberal mayor in the [primary] race,” said Steve Schale, a veteran Florida Democrat who ran Barack Obama’s efforts in the state.
Yet the publicly fiery campaign is necessary for Gillum’s wager to work: that by painting himself as an unapologetic agent of progressive change, he’ll energize the Democratic base he needs on his side, but also that he won’t alienate middle-of-the-road voters who, he hopes, will be more horrified by DeSantis’s close relationship with Trump. Gillum may not sound like Charlie Crist or Alex Sink — Democrats’ last two gubernatorial nominees — on the stump, but DeSantis is stylistically miles from Rick Scott, Crist, and Jeb Bush — Republicans’ last three governors.
And that’s the point.
“Donald Trump has sort of changed the game for a lot of people. You now have people who, before, may not have ever considered a candidate with the kind of progressive values that I hold, except when you look at the alternative. Not just Donald Trump, but also the guy I’m running against, who wants to be Donald Trump,” predicted Gillum, sitting in a cramped holding room between his campaign bus and the auditorium stage. “We’re building a different kind of constituency, and it includes some of their people.”