Democrats on Tuesday won a seat in the Florida Legislature in a district that includes Mar-a-Lago, President Donald Trump’s Palm Beach estate. It’s another surprise victory in a state election — this time with strong symbolic weight.
Emily Gregory, a political newcomer with a background in public health, became the latest Democrat to win a special election and fill a previously Republican seat.
In another race in the state, Democrat Brian Nathan, a Navy veteran and electrical workers union leader, was leading a tight election in West Tampa for the state Senate, in a seat opened by the appointment of Florida’s new lieutenant governor.
Since the 2024 presidential election, Democrats have flipped more than two dozen seats in Republican or competitive states — including Arkansas and New Hampshire this month — while Republicans have yet to take any seats from Democrats.
Republican strategies treat these defeats as a “correction” after the significant gains in 2024 in Washington and in state assemblies.
Democrats see the results as a sign of growing dissatisfaction with Trump, which could last until November and influence the midterm elections. Gregory’s victory takes this trend to the former president’s “backyard”, in a state that, after years as a swing state, has clearly started to lean towards the Republican side.
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“Floridians are tired of chaos, corruption and skyrocketing prices, from supermarkets to gasoline to health insurance,” Nikki Fried, chair of the state Democratic Party, said in a statement. “They are choosing trusted leaders like Emily to stabilize things and bring back common-sense, people-focused solutions.”
A Democrat has not won the presidential race in Florida since 2012, but the state has shown signs of a blue wave in 2026. Boca Raton, about 50 km from Palm Beach, this month elected its first Democratic mayor in 45 years, in a tight race. In December, Miami voters elected, by a wide margin, the first Democratic mayor in 30 years.
Palm Beach County, where Gregory won, was once a Democratic stronghold, but Republicans have advanced strongly in recent local and federal elections. The seat she won — District 87, on the county’s coast — was held by Republican state Rep. Mike Caruso, who he had won by 19 points in 2024.
Caruso resigned in August after being appointed county clerk by Gov. Ron DeSantis, which led to the special election being called. Trump voted by mail in the race despite his national campaign against voting by mail.
At age 40, Gregory campaigned around the theme that became a Democratic mantra in 2026: cost of living. She focused on housing and health, and also explored her personal profile: mother of three children, military wife and small business owner.
His opponent, Jon Maples, 43, a financial planner and former councilman in Lake Clarke Shores, presented himself as a “conservative outsider” and an “America First patriot.” Trump had boosted his candidacy at a Republican event in Palm Beach days before the vote, even as Maples faced a formal complaint that he did not live in the district.
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In West Tampa, Nathan was trying to turn around former state representative Josie Tomkow, Republican, despite the disadvantage of resources and low projection. The vacancy in dispute arose after Jay Collins, also a Republican, was appointed lieutenant governor.
Republicans, however, won another special election for the state House, to replace Tomkow herself: Hilary Holley handily defeated Democrat Edwin Perez and went on to represent a district between Tampa and Orlando.
In practice, Gregory’s victory does not change the correlation of forces in Tallahassee, where Republicans maintain a qualified majority. Even so, her buffer mandate, which runs until the end of the year, should be busy. The Assembly still needs to pass the budget before July 1, and DeSantis called an extra session in April to redraw Florida’s electoral map for the U.S. House in time for the 2026 midterms.
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Gregory is expected to run again for the seat in the November general election, this time for a full two-year term. A reunion with Maples at the polls is a concrete possibility.
This text is an adaptation of a report originally published in The New York Times.
