What does representing President Donald Trump in the Florida Legislature mean to the first-time Democratic candidate who upset the president’s choice in his Mar-a-Lago state House district?
“It means he’s one of 180,000 constituents,” Emily Gregory told the Florida Phoenix, brushing off any special treatment for Trump hours after flipping HD 87 blue for the first time since the 2020 redistricting. “It’s incredibly important to me to serve all of them and meet their needs, and to reflect their values and interests at the Capitol.”
Gregory, a small business owner who runs a fitness center for postpartum moms, edged out financial planner Jon Maples during Tuesday’s special election by just under 800 votes. Maples was endorsed by Trump, who voted by mail days earlier.
The win was an upset. Although the district only leans red, Trump had won it by 11 percentage points in 2024, and the seat’s previous occupant, Republican Rep. Mike Caruso, held it by a 19 percentage point margin that same year.
Gregory says she pulled off the victory by speaking with voters about their top issue: affordability across the board.
“They need lower housing costs. They need the Legislature to tackle property insurance. We need to expand accessible and affordable healthcare … and we need to strengthen our public schools,” she said.
While Gregory’s win was a shock to Florida, which rapidly became a deep red state in the aftermath of the Covid-19 pandemic — the GOP has a supermajority in both chambers — it was still a special election. Special elections are called when a seat needs to be filled before a general election. The previous occupant, Caruso, left in August to become Palm Beach County’s circuit court clerk and comptroller.
These elections tend to inspire lower participation: Trump won HD 87 by 11 percent in 2024 with more than 75% voter turnout. Tuesday night, Republicans lost by 2% with a 29% turnout. During a January 2024 special election, lower turnout helped Democrat Tom Keen upset Republican Erika Booth in an Orlando House seat — but she promptly won the rematch during the November general election.
Still, Democrats have rarely flipped seats in the past few years. Tuesday night, they did it in both HD 87 and Senate District 14. Former House Rep. Josie Tomkow, a Republican with a massive GOP machine at her back and hundreds of thousands of dollars to boot, lost to Democrat Brian Nathan — even though the Democratic Party spent hardly anything in his race.
Gregory, meanwhile, received $30,000 from the Florida House Democratic Campaign Committee, $3,000 from the Florida Democratic Party, and $10,000 from the Florida Democratic Legislative Campaign Committee. The state party provided nearly $4,000 in in-kind support, CBS12 reported.
Both Gregory and Nathan will have to quickly buckle down and prepare for the impending challenges in November, during the regularly scheduled general election.
“For the reelection, we got to turn around and do this again. Run it back,” Gregory said. “We’re going to do exactly what we’ve been doing. I’m extremely proud of the campaign we’ve run, in all of the hard work we’ve put in and we’re going to keep doing that.”
Florida Phoenix is part of States Newsroom, a nonprofit news network supported by grants and a coalition of donors as a 501c(3) public charity. Florida Phoenix maintains editorial independence. Contact Editor Michael Moline for questions: info@floridaphoenix.com.
