
Democrat Emily Gregory flips Florida House District 87, which includes Mar-a-Lago
Key Takeaways
- Democrat Emily Gregory defeated Trump-endorsed Jon Maples in Florida House District 87.
- The district includes Mar-a-Lago, President Trump's Palm Beach estate.
- The victory flips a Republican seat, signaling Democratic momentum ahead of the 2026 midterms.
Democratic Upset in Trump Backyard
Democrat Emily Gregory won the Florida House District 87 special election, flipping a district that includes President Donald Trump’s Mar-a-Lago estate.
“Democrat Emily Gregory won a Florida special election on Tuesday, flipping a state legislative district that is home to Mar-a-Lago, the Palm Beach estate that President Donald Trump counts as his residence”
The district had been represented by Republican Mike Caruso, who resigned to become Palm Beach County’s clerk.

With almost all votes counted, Gregory led by 2.4 percentage points, about 797 votes.
President Trump endorsed Maples and even voted by mail in the election, a reminder of the competitive stakes in his home turf.
This result marks a notable Democratic pickup in a district that Trump carried in 2024, and DLCC president Heather Williams framed it as a sign Republicans should worry: 'Mar-a-Lago just flipped red to blue, which should have Republicans sweating the midterms.'
National Signal of Momentum
The victory in Trump’s Palm Beach County backyard was widely framed as a sign of trouble for Trump’s faction of the GOP and a sign that Democratic energy is building heading into the 2026 midterms.
Al Jazeera called it 'the latest sign of strain for Trump’s Republican Party.'

The Hill described Democrats’ Florida gains as 'a good night' in districts Trump carried in 2024, signaling potential in red states more broadly.
Bloomberg framed the race as a landmark moment: 'A Democrat is poised to represent President Donald Trump and his Mar-a-Lago residence in the Florida state House of Representatives after Republicans lost a special election in a surprise upset.'
The Straits Times noted that Trump had won the district in 2024 and placed the results in the larger national energy.
The New York Times highlighted Democrats’ post-2024 momentum, noting that '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.'
Local Context and Significance
The district had been carried by Trump in 2024 and was previously held by Mike Caruso, who won by double digits in 2024.
“Democratic candidate Emily Gregory is projected to win a special election for a Florida state House of Representatives seat that includes United States President Donald Trump’s Mar-a-Lago resort, in the latest sign of strain for Trump’s Republican Party”
WTSP-TV Tampa highlighted that House District 87 includes Trump’s Mar-a-Lago residence.
WPTV noted that Florida Democrats claimed momentum after two upset wins in Tuesday’s contests.
The Mercury News emphasized the district’s long GOP dominance, noting it had been held by the GOP for decades and that Trump carried it in 2024.
The Orlando Sentinel framed Gregory’s win as a symbolic moment, calling it a very big deal and noting the district’s high-profile ties to Trump’s Palm Beach County home.
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