Democrat Emily Gregory Wins Florida House Special Election at Mar-a-Lago District
Democrat Emily Gregory won the special election to represent a Florida state House district that includes President Donald Trump's Mar-a-Lago home, a stunning upset signaling Democratic momentum ahead of the 2026 midterms.
Objective Facts
Gregory secured the seat by a 2.4 percentage point margin, or 797 votes, winning 51.2% of the votes against Maples' 48.8%. Gregory is the owner of a fitness company that works with pregnant and postpartum women, and she has never run for elected office before. The special election was held to fill the seat previously held by Mike Caruso, a Republican who resigned in August to become Palm Beach County clerk. Caruso, who won District 87 in the 2024 election by nearly 20 percentage points, was appointed by Gov. Ron DeSantis. Florida's 87th District is the 10th GOP-held state legislative seat Democrats have flipped around the country since Trump took office again last year. Republicans have not flipped any Democratic state legislative seats during that time.
Left-Leaning Perspective
Democrats hailed the victory in the previously Republican-controlled House District 87 as a sign voters are turning against Republicans and Trump before November's midterm elections. Democratic Legislative Campaign Committee President Heather Williams stated: "If Mar-a-Lago is vulnerable, imagine what's possible this November." She said Tuesday's race was the 29th seat that Democrats have flipped from Republican control since Trump took office, adding "Gas prices are spiking, grocery costs are up, and families can't get by – it's clear voters at the polls are fed up with Republicans." After her win, Gregory received congratulatory phone calls from Democrats across the country, including former President Joe Biden. She explained her motivation: "I felt that the leadership in Tallahassee and the legislature was not listening to us. I felt they were very distracted on culture war issues and not solving the very real affordability issues that us average Floridians are struggling with, like property insurance and health care and education." Florida Democratic Party chair Nikki Fried said: "Democrats can run and win anywhere — including Donald Trump's backyard." Left-leaning outlets frame this as evidence of a broad anti-Trump and anti-Republican sentiment emerging in reliably red areas. They emphasize affordability messaging resonated with voters despite Republican resource advantages. They largely omit Trump's substantial local popularity—he won the district by 11 points in 2024—and the unique dynamics of low-turnout special elections, instead treating the result as indicative of November momentum.
Right-Leaning Perspective
The Republican National Committee stated that special elections are not always the best barometer of things to come, with Senior Adviser Danielle Alvarez emphasizing that a low-turnout state House special election is a snapshot of local quirks, candidate dynamics, and turnout math—not some grand verdict. Florida House Republican Campaign Committee Chair and Speaker-Designate Sam Garrison acknowledged: "Jon fought valiantly in the face of low Republican turnout due to awkward Special Election timing, and despicable, dark-money racial attacks from Democrat criminal defense lawyers pretending to be Republicans." Republican strategist Jesse Hunt told Fox News: "Historically, special elections have been a poor barometer for what will occur during regularly scheduled midterm or presidential elections. Specials have unique dynamics that don't play as much of a factor when the broader electorate feels the muscle memory of showing up to vote in November." Longtime Republican strategist Colin Reed pointed to the GOP's One Big Beautiful Bill Act, the massive measure passed along party lines last summer by Republicans, which includes numerous tax cuts that many voters will feel this spring. Right-leaning voices contextualize the loss as a product of special election dynamics and timing rather than broader Republican weakness. They argue Democrats are overplaying the significance and point to Republican structural advantages that will matter more in general elections.
Deep Dive
This special election occurred in the context of broader Democratic momentum in state legislative special elections since Trump's 2025 return to office. Florida's 87th District is the 10th GOP-held state legislative seat Democrats have flipped around the country since Trump took office again last year, while Republicans have not flipped any Democratic state legislative seats during that time. The district itself was heavily Republican: GOP incumbent Mike Caruso won re-election by 19 percentage points in 2024, and President Donald Trump carried the area by about 9 points that year. Yet former Vice President Kamala Harris did win Palm Beach County by less than a point in the last presidential election, suggesting underlying shifts in this coastal area. Both narratives capture real dynamics: Democrats genuinely have flipped 29 state legislative seats since Trump took office—an unusual pattern—while Republicans correctly observe that special elections have fundamentally different electorates and dynamics than general elections. The left accurately identifies that affordability messaging resonated even in a Trump-won district, but may overstate how much this applies to November's general electorate. The right appropriately notes special election limitations but underestimates whether declining Trump approval and persistent inflation concerns could actually reshape November turnout patterns. The vacancy itself—lasting seven months—likely suppressed Republican enthusiasm in a low-turnout race where such enthusiasm typically decides special elections. Gregory's specific victory appears driven less by anti-Trump sentiment than by granular local organizing around insurance costs, housing, and education, combined with low special election turnout favoring the more engaged Democratic base.