Emily Gregory’s victory in a district previously held by Republicans is the latest Democratic upset ahead of the November midterms.
Published: March 25, 2026
Democratic candidate Emily Gregory is expected to create tension among Trump’s Republican Party in the recent special election for the Florida House of Representatives, which includes President Donald Trump’s Mar-a-Lago resort.
With nearly all votes counted in Tuesday’s election, Gregory is leading his Trump-backed opponent, Jon Maples, by 2.4 percentage points, the Associated Press reported.
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Democrats hailed the victory in the previously Republican-held 87th House District as a sign that voters are turning against Republicans and Trump ahead of November’s midterm elections. Democrats have won electoral victories in the November 2025 gubernatorial and mayoral elections, with the cost of living a prominent issue on people’s minds.
The U.S. decision to join Israel in attacking Iran is driving up oil and gas prices, putting additional inflationary pressure on Americans.
“Imagine what will happen this November if Mar-a-Lago is vulnerable,” said Heather Williams, chairwoman of the Democratic Legislative Campaign Committee. She said Tuesday’s primary is the 29th seat that Democrats have wrested from Republican control since Trump took office.
“Gas prices are skyrocketing, food costs are rising, families are becoming unlivable, and it’s clear that voters at the polls are fed up with Republicans,” Williams said.
Gregory grew up north of Palm Beach in Stuart. She owns a fitness company targeting pregnant and postpartum women and has never previously run for elected office.
She told MSNOW after her win that she was “very shocked” and had “quite an out-of-body experience.”
Gregory’s victory is the latest in a series of improbable special election results across the country, including several notable Democratic victories in Republican-controlled Florida since Trump returned to the White House more than a year ago.
In December, Eileen Higgins won Miami’s mayoral election, the first time a Democrat has led the city in nearly 30 years. She defeated a Trump-backed Republican in a campaign that leaned heavily on criticism of the president’s immigration crackdown, a message that resonated with the city’s large Hispanic population.
Further west in Texas, Democrat Taylor Rehmet flipped a reliably Republican state Senate district in a January special election.
Despite supporting the Republican candidate, Trump immediately distanced himself from the 2024 loss in a district he won by 17 percentage points, saying, “I’m not involved in that.”
Trump, whose residence is Mar-a-Lago, voted by mail in Tuesday’s election and had his ballot counted, according to Palm Beach County voter records. He chose to vote by mail even though he publicly denounced the method as a source of fraud and urged Congress to reduce it.
