Emily Gregory Wins Trump's District in Florida Upset
Democrat Emily Gregory won a Florida House special election in Trump's Palm Beach backyard, defeating his personally endorsed Republican candidate.
Emily Gregory woke up Wednesday as Donald Trump’s new state representative, and she had a message for the president: call her.
“He’s welcome to call me, as I am his new state representative,” the Democrat told the Associated Press, noting she “would love to have a conversation.”
Gregory’s surprise victory in a Florida House special election Tuesday sent shockwaves through both parties. Her District 87 is anchored by Palm Beach, and it includes Trump’s Mar-a-Lago resort. That geographic fact alone turned a state legislative race, normally an afterthought on the national political calendar, into a headline that Democrats across the country seized on with undisguised glee.
The 40-year-old first-time candidate owns a fitness company serving pregnant and postpartum women. She defeated Republican Jon Maples, a candidate Trump had personally endorsed, writing that Maples was backed “by so many of my Palm Beach County friends.” Trump also cast a mail ballot in the race himself.
For Florida Democrats, who have spent years watching Republicans consolidate power in what was once the nation’s premier battleground state, the victory felt like something more than a single seat flipped.
“The pendulum swings in both directions,” Florida Democratic Chairwoman Nikki Fried told reporters. “Last night it swung hard in the state of Florida. If we can win in Donald Trump’s backyard, we can win anywhere.”
Florida Republican Chairman Evan Power did not return a request for comment.
Gregory’s win fits a broader national pattern. Democrats have now flipped a string of seats through special elections, building a narrative of momentum heading into midterm election season, when voters will render their first major verdict on Trump’s second term. In the Tampa area, Democrat Brian Nathan holds a narrow lead in a state Senate special election that the Associated Press has not yet called. The margin falls within the range that triggers an automatic recount under Florida law.
Gregory herself pushed back against any framing of her campaign as an anti-Trump crusade. She told the AP she deliberately kept the president out of her pitch to voters, focusing instead on the pressures her neighbors face every day: surging homeowner and flood insurance rates in a hurricane-prone region, rising grocery and gas prices, and access to health care.
“I just see myself as very embedded in my community, very representative of District 87,” she said. “And I’m so humbled and proud to be their representative.”
She called herself a lifelong “proud Florida Democrat” but rejected the role of opposition leader. In Tallahassee, she said she plans to push legislation targeting insurance rate hikes, expanding health care access, strengthening public education, and relieving what she described as “huge, crushing burdens on the average Florida family.”
Gregory also credited what she called her political “naiveté” as a strength. Because she did not fully grasp how Republican the district’s voter registration was, she never talked herself out of competing. She said she believed in herself throughout the race, even when the conventional wisdom around her did not.
That confidence proved warranted. Her win is a concrete example of what Democratic operatives have been arguing for months: that candidate quality and hyperlocal economic messaging can overcome registration disadvantages in districts that Republicans have long taken for granted.
South Florida and the broader peninsula have leaned sharply rightward in recent election cycles, driven in part by Republican gains among Latino voters in Miami-Dade and other heavily immigrant communities. Fried and other state party leaders are betting that voter frustration over insurance costs and economic pressures can help reverse some of those trends before the 2026 midterms.
Gregory, for her part, is not waiting for a broader political wave to define her tenure. She says she is going to Tallahassee to work. And if the president wants to weigh in on the legislative agenda for his own district, she left the door open.
Her number, presumably, is easy enough to find.