While Florida Democrats basked in the glory of flipping two Republican-majority legislative districts into victories the previous night, the chairman of the Florida GOP wasn’t ready Wednesday to concede it augured anything too significant for November.
“We have this before; special elections aren’t just that: special,” said Republican Party of Florida Chair Evan Power in a text message. “It is not indicative of what can be expected in a general election. Just ask Tom Keen, the Orlando Democrat who won a Special Election in House District 35 in 2024 to later lose to Republican Erika Booth just a few months later.”
Keen did flip that traditionally Republican-leaning seat in January 2024 by 589 votes, similar to Democrat Brian Nathan’s 408-vote margin over Republican Josie Tomkow in the Florida Senate District 14 race in Hillsborough County Tuesday night. Keen then lost the rematch to Booth in November 2024.
In the other major upset of the evening, the Florida House District 87 special election in Palm Beach County, Democrat Emily Gregory defied the odds and defeated Republican Jon Maples by 797 votes. Republican Mike Caruso won the seat by 19 points in November 2024.
Chris Mitchell is a Democratic strategist who was involved in Gregory’s campaign. He agrees special elections are “unique environments” and not always perfect predictors for November, but sees signals Republican shouldn’t ignore.
“In both Palm Beach and Hillsborough, Republicans had a turnout advantage over Democrats. Despite that, we still won. That doesn’t happen in a vacuum. It suggests that either Democrats significantly over-performed with NPAs (no party affilation voters), saw meaningful Republican crossover, or some combination of both,” he said.
“In a low-turnout special election, those dynamics are even more notable,” he said. “If that kind of movement is happening now, it raises real questions about what the electorate could look like in a higher-turnout environment.”
Anthony Pedicini is a Republican strategist who worked on the Tomkow Senate campaign.
“Special elections are indeed special,” he told the Phoenix in an email. “But, as a political practitioners, we are using the results as a lesson — how to improve our tactics and strategies that will allow our clients to outperform the atmospherics and events beyond our control. Elections aren’t won or lost ‘just because’ and we have proved time and time again, a seat lost in a special can be regained in a regularly scheduled electoral event with a great candidate, great message and great execution.
“Republicans at all levels need to understand we will need to stand together or … you know the expression,” he added.
Florida Democratic Party Chair Nikki Fried insists this year will be different.
“The infrastructure building that the state party has done for the last few years is to make sure that we’re not only winning special elections, not only are we going to win it in 2026, when the temperature is so hyped right now, but to make sure that the infrastructure’s in place for ’28, ’30, and beyond, and that’s what we’ve really been focusing on the last few years,” she said during a Zoom press call Wednesday morning.
Outside money
Perhaps more importantly for the Florida Democratic Party, Tuesday night’s results could boost statewide candidates who have seen campaign financing from Democratic Party-aligned groups outside the state crater since Florida lost its reputation as a swing state following the 2020 election and influx of GOP voters post-COVID.
On Election Day 2022, the FDP issued a statement showing how spending from outside groups and PACs went from $58 million in 2018 to less than $2 million that year. Those numbers were equally lackluster in 2024 for the presidential, U.S. House, and Senate races.
“We have been in constant communication [with] a lot of our sister organizations,” Fried said Wednesday.
“A lot of the organizations on the national level that have been respectfully pulled out of the state of Florida over the last couple of cycles, they’re inspired by the work that we’ve been doing in the last year — these wins from December from Miami to the wins in Boca, flipping the Fort Pierce seat, they’re seeing last year that we flipped 17 seats. That is a compelling story that something is happening in our state.
“And so, yes, I spoke to [DNC] Chair [Ken] Martin last night and numerous other national organizations including our statewide candidates today who are on phone-banking of donors today. So, we do think that, based on this, that there is energy coming from our state-wides and that they are seeing the wins at the local levels and that they are inspired by the infrastructure that is being built here.”
Martin did issue a statement Tuesday night congratulating Gregory on her victory, saying that if “Democrats can win in Trump’s own backyard, we can win anywhere. From now until November, Democrats are all gas and no brakes as we compete across every corner of Florida and the nation.”
Orange County Mayor Jerry Demings, competing for the Democratic nomination for governor, said in a statement that Nathan and Gregory’s victories “prove Florida is a major battleground this election year and beyond.”
“These flips in these Trump-won districts show there is an appetite for change now and in November,” he said.
But Power points out that not only did Republican Hilary Holley win decisively in the House District 51 seat in Polk County, previously held by Tomkow (a solidly red district) that was also on the ballot on Tuesday; he also notes the more than a dozen Republicans who have won in local elections this month from Boca Raton to St. Pete Beach.
“Republicans are leading on the issues that matter to most Floridians — public safety, economic growth, meaningful property tax reform, expanded school choice, and strong environmental stewardship,” he said. “Our record isn’t just strong, it is unmatched.”
Where was Ron?
One thing Republicans aren’t wondering publicly but certainly are privately is where was Gov. Ron DeSantis and Lt. Gov. Jay Collins during the campaign?
One strategist who wanted to remain anonymous to avoid retribution said that if DeSantis had done just one public event for Tomkow, “He would have put her over the top.”
Also missing in action was Collins, who vacated the seat after being appointed to the LG position and is now running to succeed DeSantis as governor. The GOP strategist wondered why he wouldn’t be working to get another Republican elected to the Senate who could presumably help his own legislative efforts if he is elected this fall.
Money isn’t everything?
Republicans will undoubtedly have more money than the Democrats to spend on legislative races this fall, but money certainly wasn’t an issue in the SD 14 race. Tomkow raised $324,475 in contributions in her regular account since November, and an additional $319,850 in one of her political committees, Friends of Josie Tomkow. Through a second political committee, she made a $500,000 contribution to the Florida Republican Senatorial Campaign Committee on March 16.
Nathan raised $101,510 in his campaign account.
Fried acknowledged she would prefer her candidates not get outspent on a 10-1 basis, but said Democrats have been flipping seats despite the “tremendous overspending by Republicans. It’s not working. The people in this country are waking up.”
Focusing on the voters
Democrats believe they have found the formula the party has been searching for nationally since Trump regained the White House 14 months ago. The issue is whether to focus on the president or to emphasize what they can do to improve people’s lives. The fact is that, while the president is floundering in the polls, the Democratic brand is still at its lowest level in years.
Speaking to MS Now Wednesday, Gregory said her strategy when it came to Trump (whose Mar-a-Lago residence is within her district) was to “block out the noise.” She focused her campaign, she said, around “all of the voters of District 87, not the most famous one.”
Kelly Dietrich, a longtime Democratic strategist and CEO of the National Democratic Training Committee, which provided free campaign training for both Nathan and Gregory, said that is the right formula for Democrats going into November
“The Trump brand, and therefore by definition the Republican brand, is toxic right now and voters want people with solutions who are going to make their life better,” he said. “That’s what Democrats have to run on: Don’t get sidelined, don’t get distracted by all the chaos of the trainwreck that Trump is creating. Channel that chaos into how you’re going to make change for your voters.”
Meanwhile, Evan Power with the RPOF notes that with a nearly 1.5 million-voter registration advantage in the state, the Republicans remain “well-positioned and fully energized as we head toward November.”
“We will continue to engage, mobilize, and lead,” he says, adding, “Stay tuned!”
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