"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; on Monday, they sent the first 90 of what eventually will be 300 organizers across the state in an effort to improve upon the party's connection with African American and Hispanic voters. Penalosa 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 reelection 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?"