Democrat Emily Gregory Flips Trump's Mar-a-Lago District in Florida Special Election

Democrat Emily Gregory defeated Republican Jon Maples in a special election for Florida House District 87, flipping a coastal Palm Beach County seat that had been in Republican hands for decades and marking the first Democratic win in the district this century. Gregory received 17,047 votes, accounting for 51.15% of the total, while Maples received 16,281 votes, or 48.85%, in a final tally of 33,328 ballots cast.

Gregory, 40, has spent seven years running FIT4MOM Palm Beach, a fitness community for pregnant and postpartum women. A South Florida native who grew up in Stuart before settling in Jupiter, she holds a bachelor's degree in health and exercise science from Wake Forest University and a Master of Public Health in health policy and management from Columbia University, with a career spanning mental health, state government, and public health. She had never run for elected office before.

Although the shadow of the president loomed large in his home district, both Gregory and Maples mostly focused on the issue of affordability during the campaign, a subject that proved successful for Democrats in 2025 elections and one that Republicans have struggled to own during Trump's second term. In a statement Tuesday night, Gregory said: "Tonight's result sends a clear message that people want Florida to move in a new direction, one where leaders focus on lowering costs and standing up for working families. Floridians are being squeezed by rising housing costs, insurance rates, and everyday expenses, and that's what this campaign has always been about."

Maples, a 43-year-old financial planner and former Lake Clarke Shores town council member, emphasized cutting taxes and government spending, reducing regulations, and expanding school choice, and received endorsements from Trump, state Attorney General James Uthmeier, and several GOP legislators. Trump had praised Maples at an event in Florida on Saturday, calling the candidate up on stage. The Democrat's victory came after Trump himself cast a mail-in ballot, according to public records, despite his years-long criticism of voting by mail.

Mike Caruso, who won reelection in 2024 by 19 percentage points, left the seat to become the Palm Beach County clerk and comptroller. Trump had won the district by 11 points during the 2024 presidential election. Nearly two months passed before Gov. Ron DeSantis called the election in late October, a delay that prompted Gregory to sue, arguing voters were being denied representation, and the lag meant residents had no voice in Tallahassee during the 2026 Legislative Session.

The race drew significant attention and money, with more than $1 million spent between the two candidates, making it one of the more high-profile local contests in recent months. Gregory's campaign also drew criticism last week for a political text attacking Maples that some argued featured racially charged imagery and misleading claims about his residency and voting record, with the message linked to a political committee with ties to Gregory's campaign vendor, raising questions about coordination.

Florida Democratic Party Chair Nikki Fried identified the result as proof of a statewide pattern. She said she was "thrilled to congratulate Representative-Elect Emily Gregory on this monumental victory" and pointed to "a nearly 11 point swing to the left in this hard fought race" as evidence of Democrats' long-term investment in Florida.

Heather Williams, president of the Democratic Legislative Campaign Committee, declared, "Mar-a-Lago just flipped red to blue, which should have Republicans sweating the midterms," adding that "a Trump +11 district in his own backyard shouldn't be in play for Democrats, but tonight proves Republicans are vulnerable everywhere," and that state Democrats have now flipped 29 districts red to blue since Trump's election, as "gas prices are spiking, grocery costs are up, and families can't get by."

Gregory's victory narrows the GOP supermajority by one seat but is unlikely to alter the chamber's legislative direction. Gregory campaigned on increasing public education funding, expanding healthcare access, and tackling rising property insurance and housing costs, and Palm Beach County Democratic Party Chair Howard Richman pledged she would go to Tallahassee to "protect renters and homeowners, fix healthcare, and rebuild public education."

Gregory told reporters Tuesday night she still felt "pretty shocked" by the victory and noted she didn't think much about the president being one of her constituents, pointing out that Trump is "one of 115,000 registered voters in District 87." She is expected to be sworn in between April 1 and April 4.