Emily Gregory, a 40-year-old fitness business owner who had never run for office, flipped a Florida state House district that includes Donald Trump's Mar-a-Lago estate on Tuesday. She didn't make it about Trump. She made it about the cost of living.
Gregory won House District 87 with 17,113 votes (51.19%) against Trump-endorsed Republican Jon Maples, who collected 16,316 votes (48.81%) in unofficial results. Trump carried the district by about 10 points in the 2024 presidential election.
The previous Republican incumbent, Mike Caruso, won the seat by 19 percentage points in 2024 before resigning to become Palm Beach County clerk. Governor Ron DeSantis appointed Caruso to the role, triggering the special election.
A Campaign Built on Bills, Not Ballots
Gregory, a military spouse and South Florida native, runs a health and fitness company in Jupiter that works with pregnant and postpartum women. She built her entire campaign around one issue: the cost of living in Florida.
'Floridians are being squeezed by rising housing costs, insurance rates, and everyday expenses, and that's what this campaign has always been about,' Gregory said in her victory statement. 'Making Florida more affordable and making sure our state works for the people who live here.'
Her message landed in a state where the average annual home insurance premium hit $8,292 (£6,192) in 2025, an 18% jump from the previous year, according to Insurify's 2026 homeowner report. Florida has the most expensive home insurance market in the US, with premiums roughly three times the national average.
Trump's Endorsement Wasn't Enough
Maples, a financial adviser and former council member in Lake Clarke Shores, ran on tax cuts and leaned heavily into Trump's backing. Trump praised him at a Florida event days before the vote, called him 'a very successful Businessman and Civic Leader,' and urged voters to turn out.
Trump even voted by mail in the special election, despite calling the practice 'mail-in cheating' as recently as Monday.
Gregory's focus on kitchen-table issues outperformed the presidential endorsement in Trump's own back garden.
A Pattern That Keeps Repeating
The win in Palm Beach County wasn't the only Democratic flip on Tuesday night. In the Tampa area, Democrat Brian Nathan, a Navy veteran and union organiser, led Republican Josie Tomkow by just 408 votes in the Senate District 14 race in unofficial results.
Gregory's victory makes her district the 10th state legislative seat Democrats have flipped in special elections since Trump took office in January 2025. Republicans have not flipped a single Democratic seat in the same period.
'If Mar-a-Lago is vulnerable, imagine what's possible this November,' Democratic Legislative Campaign Committee President Heather Williams said.
What This Means for the 2026 Midterms
The affordability issue that powered Gregory's victory doesn't stop at the Florida state line. Home insurance premiums have climbed 46% nationally since 2021, roughly three times faster than inflation, Insurify data shows. Housing costs, grocery bills, and energy prices remain top voter concerns across the country.
Democratic candidates who've flipped Republican seats in recent special elections share a common thread. 'They are not running on a sole anti-Trump agenda,' Williams said. They talk about rent, insurance, and the bills that keep families up at night.
The Republican National Committee pushed back, arguing that special elections 'have never been predictive of general elections.' But for a first-time candidate who won Trump's own district by talking about housing costs, that line may be getting harder to sell.
