Democrats on Tuesday flipped a Florida legislative district that includes President Trump’s Mar-a-Lago estate in Palm Beach, pulling off another upset in a state house election but this time one with obvious symbolic power.
Emily Gregory, a first-time candidate with a public health background, became the latest Democrat to win a special election and claim a statehouse seat previously held by a Republican.
Since the 2024 presidential election, Democrats have flipped more than two dozen seats in Republican or battleground states — including ones in Arkansas and New Hampshire earlier this month — while the Republicans have not captured any Democratic seats.
Republican strategists have framed the losses as a natural regression following big gains in 2024 in Washington, D.C., and in state capitals across the country.
But Democrats see in the results a mounting anger in the electorate over Mr. Trump that could carry through November and the midterm elections. Ms. Gregory’s victory brought the trend into Mr. Trump’s backyard, in a state that has trended heavily Republican since its days as a perennial battleground.
A Democratic presidential candidate has not won Florida’s electoral votes since 2012, but this year, Florida has not been immune from the Democratic surge. Boca Raton, about 30 miles down the Atlantic coast from Palm Beach, elected its first Democratic mayor in 45 years earlier this month. That margin was narrow, but Miami voters in December overwhelmingly elected their first Democratic mayor in 30 years.
Palm Beach County, where Ms. Gregory scored her victory, used to be a Democratic stronghold, but Republicans have made major inroads in recent federal and local elections. The seat that Ms. Gregory won — District 87, along coastal Palm Beach County — had been held by State Representative Mike Caruso, a Republican, who won by 19 percentage points in 2024.
Mr. Caruso resigned in August after being appointed by Gov. Ron DeSantis as county clerk, prompting Tuesday’s special election. Mr. Trump voted by mail in the race earlier this month, despite his ongoing national efforts to end vote by mail.
Ms. Gregory, 40, centered her campaign on the Democrats’ favorite word in the 2026 cycle, affordability, and zeroed in on housing and health care. She also highlighted her background as a mother of three, military spouse and small business owner.
Her opponent, Jon Maples, 43, a financial planner and former council member in Lake Clarke Shores, billed himself as a “conservative outsider” and “America First patriot.” Mr. Trump promoted his candidacy a few days ago at a Palm Beach Republican event, as Mr. Maples was facing a formal complaint that he did not live in the district.
Beyond the symbolism, Ms. Gregory’s victory is not going to change the balance of power in a state legislature where Republicans hold a supermajority. Still, her term, which runs through the end of the year, promises to be eventful. Legislators still need to pass a budget before the July 1 deadline. Mr. DeSantis has also called for a special session in April to redraw Florida’s congressional map, in time for the 2026 midterms.
Ms. Gregory is also expected to run again in the November general election for a full two-year term. A rematch against Mr. Maples is possible.
David W. Chen is a Times reporter focused on state legislatures, state level policymaking and the political forces behind them.
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