Emily Gregory, a 40-year-old first-time Democrat, upset Trump‑backed Republican Jon Maples to win Florida's District 87, which includes Mar‑a‑Lago. She will complete the term of Republican Mike Caruso and must run again in November. Gregory says she will oppose an April 20 legislative session to redraw congressional maps, calling it a "power grab." Democrats view the result as potential momentum ahead of the midterms.
Emily Gregory Upsets Trump‑Backed Candidate, Wins Mar‑a‑Lago District in Florida Special Election
In this screenshot taken from video Florida State Rep.-elect Emily Gregory speaks with the Associated Press from Palm Beach, Florida, about her special election win where she flipped a district that is home to President Donald Trump's estate, Mar-a-Lago, March 25, 2026. (AP Photo)(ASSOCIATED PRESS)
Emily Gregory, a 40-year-old first-time Democratic candidate and local fitness-business owner, pulled off an upset in a Florida special election to win State House District 87 — the seat that includes President Donald Trump’s Mar‑a‑Lago resort.
A Surprise Win With National Resonance
Gregory defeated Republican Jon Maples, who had been publicly endorsed by Trump and for whom the president cast a mail ballot. Her victory flips a seat previously held by Republican Mike Caruso, who resigned to become Palm Beach County clerk. Gregory will be sworn in to finish Caruso’s term and must run again this November if she wants to keep the seat.
FILE - An aerial view of President Donald Trump's Mar-a-Lago club in Palm Beach, Fla., on Aug. 31, 2022. (AP Photo/Steve Helber, File)(ASSOCIATED PRESS)
Despite the national attention on the district because of Mar‑a‑Lago, Gregory said she ran on local issues rather than focusing on the president. She emphasized constituent concerns such as rising home insurance in a hurricane-prone region, grocery and fuel prices, access to health care and support for public education.
“I will work as hard for every single one of 180,000 constituents in District 87, and not elevate anyone over the rest,” Gregory said.
Political Context And Reactions
Florida Democratic Chair Nikki Fried hailed the result as a sign of momentum for Democrats, noting a narrow lead in a Tampa-area state senate race for Democrat Brian Nathan that is within the state’s automatic recount margin. "If we can win in Donald Trump's backyard, we can win anywhere," Fried said.
President Donald Trump speaks during the swearing in for Homeland Security Secretary Markwayne Mullin in the Oval Office of the White House, Tuesday, March 24, 2026, in Washington. (AP Photo/Alex Brandon)(ASSOCIATED PRESS)
Republicans remain dominant across Florida state government and are widely seen as favorites to retain the governor’s office in November, but Democrats argue that recent special elections show tighter margins and voter openness to their message.
Gregory expects to be sworn in before an April 20 special legislative session that Republicans scheduled to redraw congressional maps. She called the session a "complete power grab" and said she will oppose efforts she views as gerrymandering to benefit Republicans.
On the Republican side, campaigns acknowledged the need to reassess strategy but emphasized their broader goals. Ryan Smith, chief strategist for Byron Donalds’ gubernatorial campaign, said the team would continue executing its plan to "deliver real results and defend the Florida Dream."
Gregory’s victory — in a district Trump carried in 2024 and one her predecessor had won by large margins — highlights how local issues, candidate quality and turnout can reshape expected outcomes in competitive districts.
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