Key moments
In a remarkable political shift, Emily Gregory emerged victorious in a Florida special election held on March 24, 2026, flipping a state legislative district that includes Mar-a-Lago, the residence of former President Donald Trump. Gregory, a first-time candidate and owner of a fitness company for pregnant and postpartum women, defeated Republican Jon Maples, who had the backing of Trump himself. This election marks a significant moment in Florida’s political landscape, particularly in a district that has been a Republican stronghold.
As the votes were tallied, Gregory led by 2.4 percentage points, amounting to a margin of 797 votes, with almost all ballots counted. This victory is particularly striking given that the district was previously represented by Mike Caruso, a Republican who resigned to become Palm Beach County’s clerk. Caruso had won the seat by a substantial 19 percentage points in the 2024 election, making Gregory’s win all the more noteworthy.
The special election was necessitated by Caruso’s resignation in August 2025, leaving the seat vacant for several months. With approximately 115,000 voters in District 87, Gregory’s campaign focused on the rising costs of living, a strategy that resonated with constituents without directly attacking Trump, who remains a polarizing figure in the area.
Gregory’s victory is not just a personal achievement but also part of a larger trend, marking the 29th seat flipped by Democrats from Republican control since Trump took office. This trend signals a potential shift in voter sentiment, particularly in traditionally Republican areas. Political analysts are closely watching these developments, as they could foreshadow broader changes in the upcoming elections.
Reactions to Gregory’s win have been swift. Heather Williams, a local political strategist, stated, “If Mar-a-Lago is vulnerable, imagine what’s possible this November,” highlighting the implications of Gregory’s success for future elections. Ken Martin, chair of the Minnesota Democratic-Farmer-Labor Party, emphasized the significance of the results, saying, “Donald Trump’s own neighbors just sent a crystal clear message: They are furious and ready for change.”
In contrast, Trump himself downplayed the election’s impact, stating, “I’m not involved in that,” reflecting his ongoing detachment from local political dynamics. However, Gregory’s comments suggest a different narrative; she remarked, “It’s impacted people’s interest in talking to me about it. He is a constituent. But I am more focused on all 115,000 voters in District 87, not just one.” This statement underscores her commitment to representing the broader community rather than being defined by her opponent’s celebrity status.
The implications of this election extend beyond just one district. Gregory’s win could signal a shift in voter priorities and a growing dissatisfaction with the status quo, particularly in areas closely associated with Trump. As Democrats look to build on this momentum, the upcoming months will be critical in determining whether this victory is an anomaly or a sign of a larger trend.
As the political landscape in Florida continues to evolve, all eyes will be on how Gregory’s victory influences the dynamics of upcoming elections. The potential for further Democratic gains in traditionally Republican areas could reshape the political map, making this special election a pivotal moment in Florida’s electoral history.
