Inside the Democratic strategy to defeat Donald Trump in Florida

Democrats are rolling out a plan to change their fortune.
Former Florida Democratic gubernatorial nominee Andrew Gillum speaks to supporters during a gathering at the Florida Democratic Party state conference, Friday, June 7, 2019, in Orlando, Fla. (AP Photo/John Raoux)
Former Florida Democratic gubernatorial nominee Andrew Gillum speaks to supporters during a gathering at the Florida Democratic Party state conference, Friday, June 7, 2019, in Orlando, Fla. (AP Photo/John Raoux)
Published June 10, 2019|Updated June 10, 2019

LAKE BUENA VISTA — For a Democratic Party determined to make Donald Trump a one-term president, the most obvious path to victory seems so simple and yet so complicated: Win Florida.

The nation’s most populous swing state is shaping up to be make-or-break in 2020 for Trump, who likely needs Florida’s 29 electoral college votes to make the re-election math work. Republicans know this, and so do Democrats, who have found success in the state just out of reach for most of the last decade.

So, as Trump prepares next week to hold a campaign re-launch in Orlando, Democrats are rolling out their own plan to change their fortune by spiking voter registration and rebuilding their ground game. But to recreate Barack Obama’s successes in 2008 and 2012, they’ll need to buck a string of narrow losses that have deflated the party faithful and sown doubt and distrust of Democratic leadership.

In interviews over the weekend and in sessions with activists at an annual leadership conference at Disney World, Democratic National Committee Chairman Tom Perez and Florida Democratic Party leaders laid out the structure of their strategy. They’re trying to recreate the massive registered voter advantage that benefited Obama in 2008, beat back Republican efforts to eat into their margins with Hispanic voters, and hurt Trump in rural areas by hammering the Trump administration’s tax policies and its struggles to help the hurricane-ravaged Panhandle.

“It’s next to impossible for Trump to win the general election without Florida,” Perez said in an interview. “That’s why Florida is a key battleground state.”

The foundation of the plan relies upon a massive effort to register hundreds of thousands of voters. The Florida Democratic Party itself has pledged to spend $2 million to register 200,000 new Democrats by March. But the bulk of a broader, ambitious voter registration effort relies on a network of nonprofits working together under the coordination of 2018 gubernatorial candidate and former Tallahassee Mayor Andrew Gillum and the massive field operation that remained intact after he fell about 33,000 votes short of becoming governor.

After his loss — a gut-punch to Democrats confident in his chances of beating congressman and Trump surrogate Ron DeSantis — Gillum set a goal of registering or “reengaging” 1 million voters. He’s bringing his fundraising prowess to the table, along with millions he controversially left unspent from his campaign in order to seed existing advocacy groups already registering voters and get them to work together.

At the same time, a campaign volunteer base that Gillum has pegged at 100,000 people remains intact under Bring it Home Florida, a nonprofit co-founded and financed by Millie Raphael, the Miami activist who led Gillum’s Hispanic outreach and volunteer operations. Raphael says the group, which only activated last week, is working with other progressive organizations to register voters while also sending its own people into communities where no one is working to find voters who aren’t participating.

“We’re coordinating as much as we can with as many organizations as we can,” said Juan Peñalosa, executive director of the Florida Democratic Party.

Registered voter gap closing

The end game is to reverse course on the party’s slipping registration advantage over Republicans. From Obama’s first election in 2008 to the November midterms, Florida Democrats saw a nearly 700,000-voter lead over Republicans dwindle to roughly 260,000, a lead that didn’t hold up when Republicans proved even better at turning out the vote in an election where voters from both parties proved to be highly motivated.

“We registered a ton of voters in ’07 and ’08,” said Democratic strategist and pollster Steve Schale, who directed Obama’s first Florida campaign. “I think both Mayor Gillum and (former U.S. Sen.) Bill Nelson would have won had they had the electorate that Barack Obama had.”

As Democrats try to build their ranks, they’re also reinvesting in their own field operation, sending the first 90 of what eventually will be 300 organizers across the state Monday in an effort to improve upon the party’s connection with African-American and Hispanic voters. Peñalosa said about half those volunteers — 46 of whom will fan out in Miami-Dade and Broward counties and 44 in Orange, Hillsborough and Pinellas — will speak Spanish or Creole.

That effort, pitched to national donors by the DNC as part of a broader outreach strategy in nine battleground states, should help address criticisms that the state’s cash-limited party failed to properly engage minority communities last year and made a mistake by outsourcing its ground game in the most populous areas to outside political organizations until the general election. Florida strategist Craig Smith, who has worked closely with the Clintons, said the party is ensuring that the operational shortcomings it saw in Florida in 2016 won’t be repeated when donors begin to flood the state again with their money.

“You can’t spend $40 million in two months efficiently” unless an organization already exists, he said.

Smith said one of the problems Clinton faced in Florida in 2016 was, by the time she won the nomination, Trump and the Republican Party were already organized and running. In 2019, Trump is even farther ahead as a massive field of candidates jockeys for the nomination, but Smith said Democrats will catch up.

“Being three months behind in 2019 is a hell of a lot different than being three months behind in 2020,” he said. “As long as the pipeline is there when we decide the nominee, that’s all that matters.”

Democrats are also spending money on legal efforts to fight what they see as attempts to suppress the vote among left-leaning voters and to prepare for yet another recount in 2020 given the state’s history of close elections.

But there’s a difference between planning and executing, and repeated losses by 1% or less since Obama’s re-election has bred skepticism and doubt among the ranks. Losses by Gillum and Nelson in races so close they triggered unprecedented statewide recounts have encouraged the belief that Democrats are close to victory in Florida but also questions about why they keep losing.

In Orlando, where the Florida Democratic Party held its summer gala at Disney World’s Yacht and Beach Club Convention Center, frustrations over the party’s fumbles boiled over during a session held by the party’s Path to Power commission, tasked with conducting a post-mortem of the midterm elections and making a plan for 2020. Much of the party’s strategy relies on returning to the fundamentals of campaigning, but activists in the crowd wondered when the party was going to explain why the blue wave that washed over much of the country appeared to ebb on the shores of Florida.

“I didn’t see any groundbreaking ideas,” said Stacey Patel, chair of the Brevard County Democrats. “We’ve seen reports like this before, but then they sit on the shelf. How are we going to actually get this done?”

The state party and DNC hold outsized roles in Florida right now, given the discrepancy between its importance in the general election and the primary, in which Florida voters will choose their candidate after Super Tuesday. On Saturday, when the party held its gala, none of the major presidential candidates attended. Many were in Iowa, an early primary state. Some sent their spouses.

Trump, on the other hand, is highly focused on Florida, where he first rolled out his re-election campaign only one month after being sworn in and will return next week for a re-launch. His campaign manager, Brad Parscale, practically lived in the state last month, and said Florida is likely the place where the campaign will roll out its outreach effort to Hispanic voters — another battleground demographic where Democrats are trying to win back votes.

Republicans have also significantly outraised Democrats on both the state and national level, and are humming in Florida under the leadership of new Gov. DeSantis. They continue to tout their expansive digital operation, although new DNC finance chairman and Coral Gables attorney Chris Korge recently told the Miami Herald that he’s both confident that the party will hit its financial goals and impressed at how much the DNC has improved its own data operation.

Outreach to people of color

Peñalosa, executive director of the Florida Democratic Party, stressed in Orlando over the weekend that the party is spending $2 million on outreach and advertising to voters of color in the off year, ahead of 2020. The party has launched an ad campaign in black-owned newspapers and has for the first time hired a Spanish media director who is helping to book Democrats on Spanish-language TV and radio, create programming, and coordinate messaging in Miami, Orlando, Tampa and Puerto Rico.

“We’ve never really done that in a concerted way in the party, build a stable. We’re doing that media market by media market,” said Peñalosa. “We’re identifying folks with real stories who speak Spanish to talk about what this administration has done to affect their lives.”

The party has reason to invest. Perez said a DNC analysis recently showed that there are 400,000 “unregistered Latino voters in Florida who are likely Democrats.” Democrats are also vulnerable. This fall, DeSantis performed significantly better than Trump in heavily Cuban and Venezuelan precincts, and U.S. Sen. Rick Scott far outperformed Trump with Puerto Rican voters.

Trump remains overwhelmingly unpopular with Hispanic voters and has continued to amp up his immigration rhetoric. But he only needs to do marginally better with the demographic in order to be successful. This year, he has gone on an aggressive campaign courting Cuban, Venezuelan and Nicaraguan voters in South Florida by taking a heavy hand against leftist regimes in Latin America and the Caribbean.

Meanwhile, a recent national survey of 1,000 Latino voters by Trump’s polling firm, McLaughlin & Associates, found that the president has room for growth among Hispanic voters and that a Republican branding campaign to label all Democrats as socialists has the ability to hurt Democrats with a key constituency.

“We need to take this socialism thing head-on,” Perez said Saturday as he spoke to a group of Democrats who’d gathered to hear the Spanish-media director talk about the party’s Spanish-media coordination efforts. “Understand that in our community it actually could have traction unless we really take it on.”

But if Trump believes Democrats are vulnerable with traditionally Democratic voters, Democrats believe Trump is vulnerable with blue collar voters in rural Republican strongholds. Before heading to Orlando, Perez visited the Florida Panhandle, where his team filmed a campaign-style video of him talking to families living amid debris piles and in hurricane-battered trailers.

Trump signed a $19.1 billion disaster bill this month, and recently made his own visit to the Panhandle, where he announced plans to increase federal financial assistance. But two years after Hurricane Maria racked heavily Democratic Puerto Rico, Florida’s liberal party is now trying to highlight how little federal aid has come to northwest Florida more than seven months after it was hit by a Category 5 storm.

“What I saw there was sheer incompetence,” Perez said in a speech during the party’s gala.

For Florida Democrats, the question now is whether the party can competently execute its own plan, and whether that plan is competently put together. Perez told a packed ballroom Saturday night that as long as they stay on message about what Democrats are doing for the country and the state, they’ll like the results come 2020.

“Some reporter asked me the other day when I was up in Tallahassee, ‘Are you going to give up on Florida because you lost in 2016?’ ” Perez said. “I told him ‘Hell, no!’ We are re-doubling our efforts in Florida. And what we are doing, and how we are doing it, is how we will win.”