Democrat Emily Gregory won a special election for Florida’s House District 87, flipping a Republican-held seat that includes President Donald Trump’s Mar-a-Lago estate in Palm Beach. Gregory defeated Trump-endorsed Republican Jon Maples, securing 51% of the vote to Maples’ 49%, according to election results.
The district, which Trump carried by double digits in the 2024 presidential election, had been held by Republicans for years. Former state Rep. Mike Caruso, a Republican, won the seat by 19 percentage points in 2024 before resigning to take a county position, triggering the special election.
Gregory, a first-time candidate and small business owner, campaigned on affordability issues, including rising costs of living, healthcare, and support for working families. Maples, a financial planner and former local council member, focused on cutting taxes, reducing regulations, and promoting private sector job creation.
Trump endorsed Maples and urged voters to support him, calling him a “very successful Businessman and Civic Leader.” Despite the president’s backing, Gregory’s victory marks a significant shift in a district that has historically leaned Republican.
Democrats have performed well in special elections during Trump’s second term, flipping nearly 30 Republican-held state legislative seats since he took office in 2025. The midterm elections, scheduled for November, will feature races for the U.S. House of Representatives, a third of the U.S. Senate, and multiple state races for governor and legislature.
Gregory’s win adds to a string of Democratic gains in state legislative races, raising questions about Republican vulnerabilities ahead of the midterms. The Democratic National Committee celebrated the victory, with Chair Ken Martin calling it a sign of momentum for the party.
Republicans maintain a majority in the Florida House, but the flip highlights potential challenges in districts that have traditionally favored the GOP. The race drew national attention due to its location and the symbolic significance of flipping a seat in Trump’s home district.