Democrats Flip Trump’s Mar-a-Lago District In Florida Special Election Upset

Democrats flipped a reliably red Florida state House seat that includes President Donald Trump’s Mar-a-Lago estate on Tuesday, scoring a narrow but symbolically significant victory in a special election that drew national attention.

Democrat Emily Gregory defeated Trump-endorsed Republican Jon Maples in House District 87 by just over 2 percentage points, according to unofficial results. The win marks an approximately 11-point swing toward Democrats compared to the 2024 performance in the Palm Beach County district.

Gregory, a first-time candidate who runs a fitness center for postpartum moms and has a background in public health and mental health administration, campaigned on affordability, taxes and kitchen-table issues. Maples, a financial planner and former local council member, had received an endorsement from Trump, who along with first lady Melania Trump and their son Barron voted by mail in the contest.

“I think it demonstrates where the Florida voter is,” Gregory told Politico after her victory. “They want someone who is focused on solutions and the issues and not focused on the noise.”

Democrats also picked up a narrow win in a Tampa-area state Senate seat, where union leader and Navy veteran Brian Nathan defeated former state Rep. Josie Tomkow by a slim margin despite being outspent roughly 10-to-1.

The two Democratic victories will not alter Republican supermajorities in the Florida Legislature. But they come as the latest data point in a series of special-election overperformances and flips for Democrats in the state since Trump’s 2024 victory there – and amid a broader national trend of Democrats gaining ground in state legislative races over the past year.

Florida Democratic Party Chair Nikki Fried credited the party’s sustained organizing with the win. 

“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 in a statement. “Floridians are tired of the chaos, corruption, and sky-high prices on everything from groceries to gas and health care.”

In 2024, the House District 87 race had been held by Republican Mike Caruso, who won it by 19 points before being appointed to a local post by Gov. Ron DeSantis, triggering the special election. The contest grew heated in its final days, with sharp exchanges in mailers and text messages.

Democrats poured significant resources into the Palm Beach County race, viewing it as a chance to compete in Trump’s home turf. Republicans, meanwhile, downplayed the significance of the low-turnout special election.

In the state Senate District 14 race, which opened after DeSantis appointed Lt. Gov. Jay Collins last August, Nathan’s upset win was described as a surprise even by some Democrats. Tomkow, a rancher who previously held a House seat in neighboring Polk County, faced questions about her residency in the district.

Nathan, a union leader and veteran, was outspent by roughly 10 to 1 in the race to replace Collins and had received scant support from state Democrats. He narrowly defeated former state Rep. Josie Tomkow, a rancher who had held a House seat in neighboring Polk County. Tomkow’s residency had come under question, although she said she planned to move into the district once she was elected. But even Fried acknowledged that Nathan’s win was in state Senate District 14 was a surprise.

A separate House race created by Tomkow’s departure was won by Republican Hilary Holley by nine points – a solid victory but narrower than Tomkow’s margin in 2024.

Tuesday’s outcomes add to Democratic momentum in Florida special elections, even as the GOP maintains firm control of state government. Party strategists on both sides will be watching whether the results signal anything larger heading into the 2026 midterm cycle.