Democrats flip Florida seat that includes Trump's Mar-a-Lago home

Emily Gregory’s projected victory comes in a legislative district which a Republican candidate won by 19 percentage points in 2024.

Emily Gregory's win in Florida's 87th district is notable, as the seat was previously held by a Republican who won by 19 percentage points in 2024.

Emily Gregory's victory in Florida's 87th House District marks a significant shift in a district previously held by Republicans.

An in-depth look at Emily Gregory, the Democrat who won the special election in Florida's 87th House District, which includes Mar-a-Lago.

In a surprising political upset, Democrat Emily Gregory won Florida's 87th district—a traditionally Republican stronghold and home to Donald Trump’s Mar-a-Lago estate—sparking concern among the GOP ahead of the 2026 midterms. Gregory criticized the Republican Party and President Trump for pushing fear tactics and hypocrisy, particularly accusing Trump of undermining trust in mail-in voting despite using it himself. She attributed her victory to a campaign focused on real issues like affordable housing and grocery prices, contrasting with her opponent Jon Maples’ Trump-centric approach. Her win adds to a growing Democratic trend, with 30 state legislative seats flipped from red to blue since January 2025, while Republicans have failed to capture a single seat. Political analysts and Democratic leaders see this as a significant shift, while some Republicans dismissed the result as an outlier. Others, including former Trump supporters, blamed the president for deviating from campaign promises. Democratic leaders emphasized the symbolic blow of flipping a district that includes Trump’s residence, asserting it reflects voters’ demand for change. Gregory, a public health expert, also gained support for bringing a science- and evidence-based approach to politics.

In a stunning political upset, Democrat Emily Gregory won a special election in Florida’s District 87, which includes Donald Trump’s Mar-a-Lago residence. Her victory over a favored Republican candidate, Jon Maples, reflects a 20-point swing from the previous Republican win. Gregory, focused on issues like property insurance, public health, and education, dismissed the significance of Trump as her constituent and emphasized her commitment to the broader electorate of over 115,000 voters. Despite Trump's endorsement and vote for her opponent, Gregory avoided personal attacks on the former president, whose administration has faced criticism for rising gas prices, prolonged Middle East conflict, and a mishandled release of the Epstein files. Democrats have now flipped 29 state legislative seats since Trump's second term began, including another recent victory in Tampa, while Republicans have not gained any. These developments signal potential trouble for the GOP ahead of the midterms, with prediction markets indicating a high likelihood of Democrats reclaiming the House and possibly the Senate. The Republican Party, still tied to Trump, faces increasing internal and external challenges as dissatisfaction with his leadership grows.

Former Trump supporter Marjorie Taylor Greene has publicly condemned the former president following Democrat Emily Gregory’s surprise victory in a Florida State House district that includes Trump’s Mar-a-Lago estate. Gregory’s win, which marks a significant 21-point swing in a previously Republican stronghold, signals growing dissatisfaction among voters and raises concerns for the GOP ahead of the 2026 midterms. Greene, formerly a staunch MAGA ally, criticized Trump on social media for abandoning campaign promises and attacking allies—particularly in relation to the handling of the Epstein files and military actions against Iran. Her rebuke underscores deeper rifts within the Republican Party, with Greene warning that continued neglect of key issues could hurt Trump and the party in future elections. GOP insiders note increasing uncertainty about retaining control of Congress, as Democratic wins in special elections have become more frequent. A Trump spokesperson dismissed Greene’s criticism, labeling her a quitter.

In a noteworthy political upset, Democrat Emily Gregory won a special election for a Florida state House seat that includes President Trump’s Mar-a-Lago estate, defeating Trump-endorsed Republican Jon Maples. This district, based in Palm Beach County, had previously favored Trump by an 11-point margin, making the Democratic victory especially significant. Since Trump took office last year, Republicans have faced considerable losses in various state legislative contests, indicating broader electoral challenges for the GOP. Despite the setback, Florida Republicans remain optimistic about retaining the governorship and a U.S. Senate seat in the upcoming fall midterms. Republican officials downplayed the implications of the special election, citing local factors and low turnout, while Democrats portrayed the result as a strong rebuke of Trump from his own community.

Democrat Emily Gregory won the special election for Florida State House District 87, flipping the district—including Mar-a-Lago, home of President Donald Trump—from red to blue. Gregory defeated Republican Jon Maples with 51% of the vote, despite the district’s strong Republican leaning in past elections. The seat was previously held by Republican Mike Caruso, who had won by a wide 19-point margin in 2024 before leaving for another state role. Gregory emphasized local issues like healthcare, education, and affordability, consciously avoiding a campaign centered around Trump, unlike her opponent, who heavily touted Trump’s endorsement. Trump, who voted by mail for Maples despite opposing mail-in voting publicly, has not yet commented on the result. Gregory, describing herself as a proud Florida Democrat, expressed openness to working with all constituents, including Trump. Her victory, alongside another Democratic win in Tampa, signals potential momentum for Democrats ahead of national elections, against a backdrop of dissatisfaction with the current Republican administration and Trump's ongoing Iran conflict.

Emily Gregory, a Democrat and first-time candidate, won a surprise victory in a special Florida state legislative election, flipping a Republican-held seat that includes Donald Trump’s Mar-a-Lago resort. Gregory's win is a significant morale boost for Florida Democrats, signaling possible momentum heading into the 2026 midterm elections. Her victory came despite Trump backing her Republican opponent, Jon Maples. Gregory, 40, owns a fitness business for pregnant and postpartum women and ran a campaign focused on economic issues like rising insurance costs, rather than opposing Trump directly. She emphasized her deep ties to the community and said she'd represent all 180,000 constituents equally. Florida Democrats see her win—and another potentially close state Senate race in Tampa—as evidence of shifting political winds in a state long dominated by Republicans. Democratic leaders praised Gregory’s grassroots appeal and the broader trend of narrowing margins in typically red districts. Gregory is set to be sworn in before an April 20 session focused on redistricting, which she opposes, calling it a Republican power grab. Her victory, in a district Trump won by 11 points in 2024, reflects a notable shift in voter dynamics.

Emily Gregory's victory in Florida's 87th district marks a significant shift, as the district was previously held by a Republican who won by 19 percentage points in 2024.

Since Donald Trump's return to office, Republicans have suffered a series of electoral defeats, signaling potential trouble ahead in the 2026 midterms. In a surprising upset, Democrats recently won two special elections in Florida, including one in Trump’s home district of Mar-a-Lago, where he had endorsed the GOP candidate. Nationwide, since January 2025, Democrats have flipped 30 state legislative seats from red to blue, while Republicans have failed to flip any. These local-level victories underscore growing dissatisfaction with the Trump administration, which is grappling with low approval ratings and criticism on issues ranging from economic affordability to international conflicts. Democratic leaders credit their success to a strong focus on local engagement and campaign agendas centered on economic concerns. With record fundraising and plans to compete in 42 legislative chambers, Democrats are optimistic about broad gains. Analysts, including CNN’s Harry Enten, predict the pattern of Democratic wins could expand nationally. The GOP’s close identification with Trump’s leadership appears to be a critical factor influencing voter decisions. Democratic strategists believe that shifting public sentiment creates an opportunity not just for typical swing districts but also for contesting deeper red areas previously considered unwinnable.