Democrat Emily Gregory won a special election on Tuesday for Florida House District 87, flipping the seat from Republican control in a district that includes President Donald Trump’s Mar-a-Lago estate. Gregory defeated Republican Jon Maples, a Trump-endorsed candidate, in a race that both parties quickly seized upon as a bellwether of the national political mood.
With more than 95 percent of the vote counted, Gregory led with approximately 51.2 percent to Maples’ 48.8 percent, according to CNBC. The margin translated to roughly 797 votes out of more than 33,000 ballots cast. The result stunned observers in a district where the previous Republican incumbent, Mike Caruso, had won by 19 percentage points in 2024.
Caruso vacated the seat after Florida Governor Ron DeSantis appointed him to serve as Palm Beach County’s clerk and comptroller in August, triggering the special election. Maples, a financial adviser and former council member in Lake Clarke Shores, secured Trump’s endorsement and appeared to have the advantage in a district that stretches along the coast through Palm Beach Gardens, Jupiter, Juno Beach, and Hypoluxo, as Newsweek reported.
Trump himself had personally campaigned for Maples, praising the candidate at an event in Florida on Saturday and calling him up on stage. The president also voted by mail in the special election, and Palm Beach County voter records confirmed his ballot was counted, according to PBS NewsHour. Trump moved his primary permanent residence from Trump Tower in New York City to Mar-a-Lago in 2019.
Gregory, reportedly 40 years old, is a small business owner in the health and fitness industry who works with pregnant and postpartum women. She had never run for elected office before. A native of Stuart, north of Palm Beach, she told reporters that Trump is one of 115,000 registered voters in District 87 and that her campaign focused on lower property insurance, expanded health care, and strong public schools.
The victory sent a jolt through Democratic circles. DLCC President Heather Williams stated that the race marked the 29th seat Democrats have flipped from Republican control since Trump took office, as U.S. News & World Report noted. Newsweek’s tally placed the total even higher, counting both the District 87 race and another Tuesday special election to put the number at 30 flipped state legislative seats.
That second race also delivered a blow to Republicans. Democrat Brian Nathan, a Navy veteran and union leader, defeated Republican former state Representative Josie Tomkow in a special election for Florida’s 14th Senate District, giving Democrats two significant pickups in a single night in a state long considered solidly red territory.
DNC Chairman Ken Martin was blunt in his assessment. “If Democrats can win in Trump’s backyard, they can win anywhere across the country,” he stated. Florida Democratic Party chair Nikki Fried echoed the sentiment, telling NBC News that Democrats can run and win anywhere, including Donald Trump’s backyard.
However, Republicans pushed back against the narrative that the results carried broader national significance. RNC Senior Adviser Danielle Alvarez described the outcome as “a snapshot of local quirks, candidate dynamics, and turnout math, not a grand verdict,” according to Fox News. Special elections historically draw lower turnout than general elections, and party strategists on both sides have long debated how much predictive power such contests hold.
Still, the broader context is difficult for the White House to dismiss. NBC News reported that Trump’s approval rating at the time of the election sat in the high 30s to the low 40s in most public polling, a figure that Democrats argue is fueling their success in down-ballot races across the country.
The string of Democratic special election victories has drawn comparisons to similar patterns during previous administrations, when the party out of power in Washington used local races to build momentum ahead of midterm elections. Gregory’s triumph in a district so closely associated with the sitting president adds a symbolic dimension that transcends the single seat, as The Hill noted.
For now, Gregory will head to Tallahassee as a first-time officeholder who turned a 19-point Republican stronghold into a competitive — and ultimately blue — battleground. Whether that shift endures beyond a low-turnout special election remains to be seen, but for Democrats searching for signs of a political wave, the result in Trump’s own backyard was hard to ignore.
