Democrat Emily Gregory Flips Florida House District 87 Including Mar-a-Lago

Democrat Emily Gregory secured a stunning upset victory in Florida's House District 87 special election on March 24, 2026, flipping a Republican-held seat that includes President Donald Trump's Mar-a-Lago estate.

“Those dates are concurrent with the regular election for a two-year term”

270toWin

Gregory defeated Republican Jon Maples by a narrow margin of 51% to 49%, winning by just 797 votes out of more than 33,000 cast, according to final tallies reported by multiple sources.

270toWin

This victory represents an extraordinary 11-point political swing in a district where Trump won by approximately 11 percentage points in the 2024 presidential election and where Republican Mike Caruso had previously won reelection by 19 percentage points just months earlier.

The race drew national attention as a bellwether for political momentum in Florida and potentially the broader United States heading toward the November 2026 midterm elections.

Gregory, a first-time political candidate and South Florida native, emerged victorious despite Maples' significant financial advantage and Trump's personal endorsement.

The 40-year-old Gregory is a public health expert, Army spouse, and mother of three who owns FIT4MOM Palm Beach, a fitness company specializing in programs for pregnant and postpartum women.

AP News

Her campaign centered on affordability issues, rising property insurance costs, healthcare access, and rebuilding public education.

In contrast, Maples, a 43-year-old financial planner and former Lake Clarke Shores Council member, ran as an America First conservative with a platform focused on cutting taxes, reducing government spending, and advancing school choice policies.

Maples benefited from substantial outside support, including $440,000 in contributions and nearly $100,000 in digital and TV ad spending, while Gregory's campaign emphasized grassroots organizing and local connections.

The special election was triggered by Republican Mike Caruso's resignation from the seat in August 2025 to become Palm Beach County's clerk and comptroller, creating a vacancy in a district that encompasses Jupiter, Palm Beach Gardens, Riviera Beach, Juno Beach, Lake Park, Palm Beach Shores, and parts of Lake Worth Beach.

“It was the 29th seat Democrats had flipped from Republican control since Mr Trump regained office”

Australian Broadcasting Corporation

Despite the district's Republican leaning and Trump's strong personal endorsement of Maples—including a social media post declaring 'JON MAPLES HAS MY COMPLETE AND TOTAL ENDORSEMENT!'—Democrats framed the contest as a referendum on affordability and economic hardship.

The victory marked the 29th state legislative seat that Democrats have flipped from Republican control since Trump returned to the White House in January 2025, continuing a pattern of Democratic success in special elections across the country.

Florida Democratic Party Chair Nikki Fried celebrated the win as demonstrating that 'Democrats can run and win anywhere—even in Donald Trump's own territory,' while national Democrats saw it as evidence of growing momentum against the Republican Party ahead of the 2026 midterms.

The election was not without controversy, as questions were raised about Maples' residency within the district boundaries.

Democrats alleged that Maples had used a voter registration address associated with a motel in Palm Beach Shores during the primaries, prompting a complaint to state officials that remained under review.

BBC

Maples countered that he and his family had purchased and moved into a new home in Jupiter within the district's bounds, citing Florida law that requires candidates to reside in the district only by the time they are sworn in.

Additionally, Gregory's campaign drew criticism for a political text message that some argued featured racially charged imagery and misleading claims about Maples' residency and voting record, linked to a political committee with ties to Gregory's campaign vendor.

Despite these controversies, voter turnout remained relatively low, with only about 15% of eligible voters casting ballots ahead of Election Day—roughly 4,400 participating in early voting and about 13,000 submitting ballots by mail, according to the Palm Beach County Supervisor of Elections Office.

Gregory's victory carries significant symbolic weight as Mar-a-Lago, Trump's primary residence since 2019, will now be represented by a Democrat in the Florida House of Representatives.

“Democrats flip Florida seat that includes Trump's Mar-a-Lago home Democrats are projected to win a special election for a Florida legislative district that includes Donald Trump's Mar-a-Lago home in Palm Beach, marking another upset in the president's backyard”

BBC

The result adds to Democrats' string of special election successes in Florida, including Eileen Higgins' historic win as Miami mayor in December 2025 and Brian Nathan's narrow victory in a Tampa-area state Senate race on the same night.

BBC

National Democrats immediately seized on the win as evidence of growing momentum against Trump and the Republican Party, with Democratic Legislative Campaign Committee President Heather Williams declaring that 'Mar-a-Lago just flipped red to blue, which should have Republicans sweating the midterms.'

Meanwhile, Trump's own voting behavior drew attention as he cast a mail ballot despite his frequent criticism of mail-in voting as 'mail-in cheating,' a position reflected in his push for the SAVE America Act that would limit universal mail-in voting.

The White House defended the practice as falling under 'commonsense exceptions' for illness, disability, military service, or travel, though critics noted the apparent hypocrisy in Trump's actions.