In an unexpected turn of events that has reverberated far beyond Florida’s borders, Democrat Emily Gregory clinched victory in the special election for Florida House District 87 on March 24, 2026, flipping a seat that not only encompasses the famed Mar-a-Lago estate—President Donald Trump’s Palm Beach residence—but has also been a Republican stronghold for decades. Gregory’s win, by a margin of 2.4 percentage points (51.15% to Jon Maples’ 48.85%), marks the first time this century that a Democrat will represent the district, sending shockwaves through both parties as the nation eyes the upcoming midterm elections.
District 87, which stretches up Florida’s Atlantic coast to include communities such as Jupiter, Palm Beach Gardens, Riviera Beach, Juno Beach, Lake Park, Palm Beach Shores, and parts of Lake Worth Beach, has long been considered safe GOP territory. Just two years ago, Republican Mike Caruso secured the seat by a commanding 19-point margin, and Trump himself carried the district by roughly nine points in 2024. The seat became vacant in August 2025 when Caruso resigned to become Palm Beach County Clerk and Comptroller, leaving residents without representation for nearly two months—a delay that prompted Gregory to sue Governor Ron DeSantis for failing to call a timely election. The lawsuit was rendered moot when DeSantis eventually set the election date, but the episode became a rallying point for voters frustrated by the lack of a voice in Tallahassee during a critical legislative session.
Gregory, a 40-year-old South Florida native and first-time candidate, grew up in Stuart before settling in Jupiter. Her background is as varied as it is impressive: she holds a Bachelor of Science in Health and Exercise Science from Wake Forest University and a Master of Public Health in Health Policy and Management from Columbia University. For the past seven years, she has owned and operated FIT4MOM Palm Beach, a fitness community supporting pregnant and postpartum women. Her career has also spanned mental health, state government, and public health, all fueling her commitment to what she calls "practical, evidence-based solutions." She is also an Army spouse, adding yet another layer of relatability in a region with a significant veteran population.
Gregory’s campaign was anchored in addressing the everyday concerns of working families: affordability, public education funding, healthcare access, and skyrocketing housing and property insurance costs. She championed targeted relief for first-time homebuyers and criticized the GOP-led Legislature for focusing on divisive issues like curbing diversity, equity, and inclusion programs instead of bread-and-butter economic challenges. Her message clearly resonated, as she managed to draw support in a district where Democrats have trailed in voter registration and Republicans have long held sway.
The race itself was anything but quiet. More than $1 million was spent between the two campaigns, with Maples raising a reported $440,000 (including significant outside support from the Florida House Republican Campaign Committee) and Gregory’s total fundraising reaching approximately $325,000, bolstered by labor groups, progressive organizations, and a host of local and national endorsements. Both candidates advanced to the general election after dominating their respective primaries in January, each securing more than 80% of the vote.
Jon Maples, a 43-year-old financial planner and former Lake Clarke Shores Council member, ran on a platform closely aligned with state and national Republican priorities—cutting taxes and government spending, expanding private-sector job growth, and advancing school choice. He enjoyed the backing of high-profile GOP figures, including Trump, Attorney General James Uthmeier, and Florida Speaker-designate Sam Garrison. Yet, his campaign was not without controversy: questions arose about whether he lived within the district, prompting a formal complaint to state officials and scrutiny over his last-minute move into a Jupiter residence. Meanwhile, Gregory’s camp faced criticism over a political text message that opponents argued used racially charged imagery and misleading claims about Maples’ residency and voting record. The message was linked to a political committee associated with Gregory’s campaign vendor, raising eyebrows over potential coordination.
Despite the high stakes and intense spending, voter turnout was relatively low, with only about 15% of eligible voters casting ballots. According to the Palm Beach County Supervisor of Elections, roughly 4,400 people voted early and about 13,000 submitted mail ballots. Democratic voters slightly outpaced Republicans with 7,457 ballots cast to the GOP’s 7,176, while more than 2,800 votes came from those with no party affiliation. Notably, Trump himself voted by mail—despite his frequent public denunciations of mail-in voting as a source of fraud—adding an ironic twist to an already charged contest.
The result was met with jubilation from Democrats, who see Gregory’s win as a harbinger of shifting tides in Florida and beyond. “Donald Trump’s own neighbors just sent a crystal clear message: They are furious and ready for change,” declared Democratic National Committee Chair Ken Martin, as reported by Florida Politics. Heather Williams, president of the Democratic Legislative Campaign Committee, noted, “If Mar-a-Lago is vulnerable, imagine what’s possible this November… State Democrats have now flipped a staggering 29 districts red to blue since Trump’s election.” She added, “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.”
Florida Democratic Party Chair Nikki Fried called it a “monumental victory,” pointing to a nearly 11-point swing to the left in a district Trump won by double digits just two years ago. “This victory reiterates an undeniable trend in Florida: with year-round organizing and infrastructure investment, Democrats can run and win anywhere—including Donald Trump’s backyard,” Fried said. Local Democratic leaders echoed this optimism, with Palm Beach County Democratic Party Chair Howard Richman crediting a “seamless partnership” among the campaign, state party, and local volunteers for the win.
Republicans, meanwhile, acknowledged the sting of defeat but vowed to regroup. House Speaker-Designate Sam Garrison praised Maples for running “an extremely strong campaign” and attributed the loss to “low Republican turnout due to awkward special election timing, and despicable, dark-money racial attacks from Democrat criminal defense lawyers pretending to be Republicans.” Garrison pledged to learn from the outcome and return stronger in November, signaling that the GOP is far from conceding the district in the long run.
With her victory, Gregory expands the Democratic caucus in the Florida House and will soon head to Tallahassee to represent a diverse district that has, until now, been a Republican bastion. Her win is being hailed as both a repudiation of the status quo and a signal that, even in the heart of Trump country, voters are open to change. As the 2026 midterms approach, all eyes will remain fixed on Florida, where the political landscape appears more fluid than ever.
Emily Gregory’s upset win in District 87 stands as a vivid reminder that in American politics, even the most entrenched strongholds can shift—sometimes overnight—when voters decide it’s time for something new.