Democrat Emily Gregory flipped House District 87 in Palm Beach County blue in an upset victory Tuesday, winning 51.15% of the vote to Republican Jon Maples’ 48.85% in a race that marks the first time a Democrat has won there this century. The district runs up the coast through Palm Beach Gardens, Jupiter, Juno Beach and Hypoluxo, encompassing the area around Mar-a-Lago where President Donald Trump cast his ballot through the mail. Gregory fills a seat Republican Mike Caruso left vacant in August when he departed for an appointed job as Palm Beach County Clerk and Comptroller.
“Donald Trump’s own neighbors just sent a crystal clear message: They are furious and ready for change,” said Democratic National Committee Chair Ken Martin in a statement. “While Trump is partying with his billionaire donors and building gilded ballrooms, Americans are being left behind and raising hell with their votes. Rep.-Elect Emily Gregory ran an incredible campaign focused on Florida families’ top concerns, from the skyrocketing cost of groceries and gas to the health care crisis Donald Trump has unleashed across Florida.” The extended vacancy became a defining issue in the race itself, with nearly two months passing before Gov. Ron DeSantis called the election in late October.
“Mar-a-Lago just flipped red to blue, which should have Republicans sweating the midterms,” said Democratic Legislative Campaign Committee President Heather Williams. “A Trump +11 district in his own backyard shouldn’t be in play for Democrats, but tonight proves Republicans are vulnerable everywhere. State Democrats have now flipped a staggering 29 districts red to blue since Trump’s election.” The delay in calling the election prompted Gregory to sue, arguing voters were being denied representation during the 2026 Legislative Session.
House District 87 has trended reliably Republican in recent cycles, with Caruso winning re-election by 19 percentage points in 2024 when Trump carried the district by roughly 9 points. Both Gregory and Maples advanced to the general election after overwhelming primary wins in January, each securing more than 80% of the vote in their respective contests. The race garnered national attention as the most likely red-to-blue flip among three legislative special elections in Florida on Tuesday.
“Congratulations to State Representative Elect Emily Gregory on flipping HD 87 in Palm Beach County! So thrilled to welcome her to our Democratic House caucus!” posted House Democratic Leader Christine Hunschofsky on X. Gregory, a 40-year-old South Florida native and first-time candidate, grew up in nearby Stuart and today owns and operates a small Jupiter-based fitness center for pregnant and postpartum women. She is also an Army spouse who framed her campaign around affordability and local quality-of-life concerns.
Gregory’s platform centered on increasing public education funding, expanding access to health care and addressing rising property insurance and housing costs. During her campaign, she drew a sharp distinction with Republicans on tax policy, opposing efforts to eliminate property taxes, which she argued would shift the burden onto renters through higher sales taxes and local fees. At the same time, Gregory signaled openness to more targeted relief, such as exemptions for first-time homebuyers.
The Democrat criticized the GOP-led Legislature’s focus on curbing diversity, equity and inclusion programs, arguing that such efforts eschew more pressing economic challenges facing residents. Her campaign reported raising about $176,000 directly, supplemented by roughly $82,000 in in-kind support, with total fundraising reaching $325,000 with additional help from a political committee. Her endorsements include U.S. Rep. Lois Frankel, Florida Senate Democratic Leader Lori Berman and several local officials, as well as backing from labor groups and progressive organizations.
“If Mar-a-Lago is vulnerable, imagine what’s possible this November,” Williams said. “Democrats are clearly on offense as we prepare for the most expansive midterm strategy ever down-ballot, with 650 seats in play. 2026 is shaping up to be an election for the history books.” The victory adds to Democratic momentum as the party prepares for the 2026 midterm elections with an expanded strategy targeting legislative seats nationwide.