Florida Democrats scored unexpected victories in two special elections, flipping Republican-held legislative seats in Palm Beach County and Hillsborough County that had been considered safe for the GOP. Democrat Emily Gregory narrowly defeated Republican Jon Maples in House District 87, a seat that encompasses President Donald Trump’s Mar-a-Lago residence and had been held by Republicans for decades. In the Tampa Bay area, Democrat Brian Nathan, a Navy veteran and union organizer, pulled off a narrow victory over Republican Josie Tomkow in Senate District 14 by just over 400 votes.
“I feel so energized. So excited. To be that different voice,” Gregory said after her win. “I think change is coming and we deserve it.” The Palm Beach County victory was particularly striking given that Trump carried the district by double digits in 2024, and Democrats had not held the seat in a century. Gregory’s campaign focused on cost of living, housing, health care and schools rather than political rhetoric.
“If we can win in Donald Trump’s backyard, we can win anywhere,” said Florida Democratic Party Chair Nikki Fried. “This race wasn’t meant to be close. Democrats are always outmatched in dollars and haven’t held this seat in a century.” Fried credited the victories to grassroots organizing and direct voter engagement rather than television advertising, calling it the foundation for rebuilding the party’s infrastructure statewide.
The Senate District 14 seat had been held by Republican Jay Collins before he was appointed Florida’s lieutenant governor, and Republicans widely expected to retain control. “Brian is genuine, a hard worker, union leader, a veteran - and he just rolled up his sleeves,” Fried said. “The type of person and connection on issues matters, and that’s why you saw the victory.” Nathan’s background as a union organizer helped him connect with working-class voters in the competitive district.
Republican leaders acknowledged the setbacks while emphasizing the need for better turnout in future elections. “I think it’s a stark reminder, nothing’s promised,” Collins said. “We may have an almost 1.5 million voter advantage, but that doesn’t guarantee anything.” Collins pointed to low turnout as a contributing factor, noting it was “under 30%” in Hillsborough County and urged Republicans to maintain engagement.
“You’ve got to fight like you’re 10 points down every single day. Don’t take it for granted. Show up and vote,” Collins said. Republican state party chair Evan Power attempted to downplay the results, stating: “We have seen this before; special elections are just that: special. It is not indicative of what can be expected in a general election.” Tomkow has already indicated she plans to run again in November, setting up a potential rematch in the competitive district.
Political analyst Lars Hafner said the results reflect broader shifts in Florida’s political landscape that extend beyond typical special election dynamics. “The fact of the matter is that so many people thought Florida was ruby red, and now we’re seeing a trend toward light purple,” Hafner said. “It will make the midterm elections somewhat more interesting.” He noted that Democrats have been outperforming expectations in recent special elections across the state and nation.
“Democrats are coming out because they’re highly motivated, but we’re also seeing independents and disillusioned GOP members voting with them,” Hafner said. Independent voters, who make up roughly a third of Florida’s electorate, could prove decisive in upcoming races. “The way independents go will be the way candidates win,” Hafner said. “If they’re worried about affordability and other issues, that could help put more Democrats into office.”
Despite the victories, Hafner cautioned that sustained success requires continued investment and organization. “You can win with little money, but you can’t win with no money,” he said, emphasizing that Democrats must continue building coalitions and funding campaigns to remain competitive. The wins give Democrats momentum heading into the November midterm elections, though Republicans still maintain a supermajority in the Florida Legislature.
“People are tired of the chaos and just want good people to represent them,” Fried said. “This is going to be a perfect storm here in Florida.” The Democratic victories have prompted both parties to recalibrate their strategies as they prepare for the November midterm elections, when all legislative seats will be on the ballot.