In a surprising turn of events, Emily Gregory has won a special election for Florida House District 87, flipping the seat from Republican to Democrat. The election, held on March 24, 2026, saw Gregory leading by 2.4 percentage points, or 797 votes, with nearly all ballots counted.
This district, notably including Donald Trump’s Mar-a-Lago estate, was previously held by Republican Mike Caruso, who resigned to take a position as Palm Beach County clerk. Caruso had won the district by a significant margin of 19 percentage points in the 2024 election, making Gregory’s victory particularly striking.
Gregory’s opponent, Jon Maples, received an endorsement from Trump, who has been a dominant figure in Florida politics. Despite this backing, the results indicate a potential shift in voter sentiment against Trump and the Republican Party as the midterm elections approach.
Gregory, a small business owner with no prior experience in elected office, has now positioned herself as a significant player in Florida politics. Her win is part of a broader trend, with Democrats having flipped 29 seats from Republican control since Trump took office.
In the election, Gregory secured 51.2% of the vote compared to Maples’ 48.8%. This close contest underscores the competitive nature of the district, which was redrawn two years ago to expand its size and previously favored Republican candidates.
Reactions to Gregory’s victory have been enthusiastic among Democratic leaders. Nikki Fried expressed her excitement, stating, “I’m thrilled to congratulate Representative-Elect Emily Gregory on this monumental victory.” Meanwhile, Christine Hunschofsky noted that this win reflects the broader momentum building across Florida.
Political analysts are interpreting this result as a clear message from voters, with Ken Martin commenting, “Donald Trump’s own neighbors just sent a crystal clear message: They are furious and ready for change.” Heather Williams added, “If Mar-a-Lago is vulnerable, imagine what’s possible this November.”
As Gregory prepares to seek election for a full two-year term in November, the implications of her victory could resonate throughout the upcoming midterm elections, where 650 seats are in play. This election serves as a bellwether for potential shifts in political power in Florida and beyond.
