In a political twist that has sent shockwaves through Florida and beyond, Democrat Emily Gregory clinched a narrow but consequential victory in a special election for the Florida House District 87 seat on March 24, 2026. This Palm Beach district, which notably includes former President Donald Trump’s Mar-a-Lago residence, had been considered a Republican stronghold, making the Democratic win all the more remarkable.
Gregory, a first-time candidate, small business owner, and military spouse, defeated Trump-backed Republican Jon Maples with 51% of the vote to Maples’ 49%, according to official tallies reported by BBC and CNN. The margin was slim, but the implications were anything but. Just two years prior, Republican Mike Caruso had carried the district by nearly 20 points, and Trump himself won the area by 11 points in the 2024 presidential contest. Caruso vacated the seat in August 2025 to become Palm Beach County clerk, setting the stage for this high-stakes special election.
Gregory’s campaign, as she told MSNBC on election night, was built on a belief in the district’s potential for change. “When I started this nine months ago, I obviously thought it was possible. I might have done some crazy calculus to decide that this was a flip opportunity, but it was. And we did it. So my math worked,” she said with a sense of satisfaction and disbelief. Her campaign focused heavily on economic issues, especially the rising cost of living, which she argued was squeezing Florida families. “Everyone is feeling that affordability crisis and the last thing that Florida families needed when they’re struggling is $4 gas,” Gregory told CNN’s Erin Burnett. “Floridians are being squeezed by rising housing costs, insurance rates, and everyday expenses, and that's what this campaign has always been about: making Florida more affordable and making sure our state works for the people who live here.”
Despite the district’s deep red history, Gregory’s message resonated with voters weary of economic pressures. She emphasized that her campaign was not about Trump, despite the former president’s high-profile endorsement of her opponent and his status as a constituent. “He’s one of 115,000 registered voters in District 87,” Gregory quipped to MSNBC, downplaying the significance of Trump’s presence in the district. After her win, she reiterated her commitment to serving all residents, saying, “I would be happy to have a conversation. And you know, all 180,000 residents of District 87 are my priority if I’m so lucky to serve. I will put them all with equal weight.”
For Republicans, the loss was a stinging setback. Maples, a former Lake Shores council member, had received Trump’s “Complete and Total Endorsement” as early as January, and the former president even praised him at a campaign event just days before the vote. Republican Congressman Byron Donalds, now running for governor, also appeared in campaign ads urging voters to support Maples. Trump himself took the unusual step of voting by mail in the special election, despite his vocal opposition to mail-in voting and his party’s efforts to restrict the practice through the SAVE America Act. As CNN reported, this contradiction did not go unnoticed among local voters, with one Republican, Michelle Hall, expressing surprise: “If he’s against something, why are you doing it?”
The Democratic win in District 87 is part of a broader trend of special election upsets during Trump’s second term. Since his return to the White House in January 2025, Democrats have flipped 29 state legislative seats nationwide, according to CNN. In Florida alone, the March 24 special elections saw Democrats flip not just District 87 but also Senate District 14, where Navy veteran and union organizer Brian Nathan edged out Republican Josie Tomkow in another come-from-behind victory. Nathan’s win was similarly dramatic: he prevailed by just 408 votes in a district that had favored Republicans by double digits in recent cycles. “Brian is the kind of person we need in the legislature. His history of service as a Navy Veteran and union leader ensures that the needs of everyday people will be at the heart of every vote he takes in Tallahassee,” said Florida Democratic Party Chair Nikki Fried.
National Democratic leaders were quick to highlight the significance of Gregory’s victory. “If Democrats can win in Trump’s backyard, we sure as hell can win anywhere across the country. Onward to November!” Democratic National Committee Chairman Ken Martin declared on social media. Heather Williams, President of the Democratic Legislative Campaign Committee, echoed the sentiment: “A Trump +11 district in his own backyard shouldn’t be in play for Democrats, but tonight proves Republicans are vulnerable everywhere. If Mar-a-Lago and Tampa are vulnerable, imagine what’s possible this November.”
Gregory’s win was also celebrated by advocacy groups like Ruth’s List Florida, which works to elect pro-choice Democratic women. Christina Diamond, the group’s CEO, called the result “a direct rejection of the Florida GOP’s failed, out-of-touch agenda and proof that their politics of division are losing ground.” She added, “Across Florida and the country, women are stepping up, building winning campaigns, and leading the way forward and this is just the beginning.”
Yet, the night was not a clean sweep for Democrats. In House District 51, located in northern Polk County—a region that went for Trump by over 13 points in 2024—Republican Hilary Holley defeated Democrat Edwin Pérez by eight percentage points, 54% to 46%. This result underscored the persistent strength of the GOP in Florida’s more conservative areas, even as Democrats notch high-profile victories elsewhere.
Special elections, often marked by low turnout, place a premium on voter enthusiasm and campaign organization. In this cycle, Democrats’ focus on affordability and economic issues appears to have struck a chord, particularly in districts where voters feel left behind by rising costs and political gridlock. Gregory’s background in public health and small business, combined with her outsider status, may have helped her connect with voters seeking a change from established political figures.
With the 2026 midterm elections looming, the stakes are high for both parties. Gregory is expected to seek a full two-year term in November, as are other recent Democratic winners. For Republicans, the losses in districts like 87 and 14 serve as a wake-up call, highlighting the need to recalibrate their message and strategy in the face of shifting voter priorities.
As the dust settles, one thing is clear: the political landscape in Florida—and perhaps the nation—is far more dynamic and unpredictable than many had assumed. The results from Palm Beach and beyond suggest that even the most entrenched political strongholds are not immune to change when voters feel the pinch of everyday life and demand new leadership.