A Mar-a-Lago flip: Dems win Trump's hometown Florida House district

TALLAHASSEE, Florida — Democrats sent a jolt Tuesday through reliably red Florida, flipping two legislative seats including the district containing President Donald Trump's Mar-a-Lago home.

Democrat Emily Gregory defeated the Trump-endorsed GOP state House candidate in a hotly contested race that had seen Democrats pour money and support into an effort to take hold of the Palm Beach County district. But Democrats also narrowly squeaked out a win in a Tampa state senate seat that had been held by Lt. Gov. Jay Collins until last August.

The wins won’t change the overall control of the Florida Legislature's Republican supermajority. But the victories were quickly heralded by state and national Democrats after years of GOP domination in the Sunshine State and even jokes from Gov. Ron DeSantis that the state party was practically dead. And Tuesday's results add more tallies to a trend of Democrats flipping Republican-held seats in state legislatures across the country over the past 14 months.

Gregory, a first-time candidate with a background in public health and mental health administration who now runs a fitness center for postpartum moms, defeated Jon Maples, a financial planner who previously held a local council seat, by little more than 2 percentage points. She pulled off the victory even as Trump used his social media accounts to urge people to vote for Maples.

Back in 2024, the GOP incumbent — then-state Rep. Mike Caruso — won House District 87 by 19 points. While Democrats broadly wanted to win in Trump's backyard, the local campaign itself focused more on affordability and taxes. The contest got testy in the closing days, with supporters on both sides zinging their opponents in mailers and text messages.

The win continues a series of blue special election wins and overperformances in Florida since Trump comfortably won the state in 2024.

“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,” said Florida Democratic Party Chair Nikki Fried. “Floridians are tired of the chaos, corruption, and sky high prices on everything from groceries to gas and health care.”

State election records show that Trump, as well as first lady Melania Trump and Trump’s son Barron, all voted by mail in the House District 87 election. Trump requested his mail-in ballot on March 14, just days after he insisted that the SAVE America Act include limits on mail-in voting. Trump on Monday, during a stop in Memphis, referred to voting by mail as “mail-in cheating.”

Brian Nathan, a union leader and veteran, was outspent by roughly 10 to 1 in the race to replace by 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.

"We believe Brian just sent shockwaves across Florida," said Shawna Presley Vercher, a consultant for Nathan.

The special elections were prompted by DeSantis appointments. The governor appointed Collins last August, but he waited months before calling the special election to fill it. The Palm Beach County state House seat came open because he appointed the GOP legislator who held it to a local post.

Tomkow's decision to give up her House seat created a vacancy there that was filled by the election of Republican Hilary Holley on Tuesday. Holley won her election by nine points which was a smaller margin than Tomkow won the district back in 2024.