Emily Gregory is a first-time Democratic candidate who on Tuesday pulled off one of the most politically symbolic upsets in recent Florida history — flipping a state House seat in President Trump’s own Palm Beach County backyard.
Ms. Gregory, 40, defeated Trump-endorsed Republican Jon Maples in the special election for Florida House District 87, capturing 51.15% of the vote to Mr. Maples’ 48.85%. The district includes Mr. Trump’s Mar-a-Lago estate, where he holds legal residency.
Background and education
Ms. Gregory is a South Florida native who grew up in Stuart, on the Treasure Coast, about 20 miles north of where she would eventually settle in Jupiter. She holds a bachelor’s degree in Health and Exercise Science from Wake Forest University and a Master of Public Health in Health Policy and Management from Columbia University.
Her professional background spans mental health services, state government and public health policy, experience she leaned on throughout the campaign to position herself as an evidence-based problem solver.
Small-business owner and Army spouse
Before running for office, Ms. Gregory spent seven years as the owner of FIT4MOM Palm Beach, a fitness community offering programs such as Stroller Strides for pregnant and postpartum women. She is married to Lt. Col. Andrew Gregory of the United States Army, and the couple have three sons.
The campaign
Ms. Gregory ran on a platform centered on affordability, expanding health care access, increasing public education funding and tackling Florida’s rising property insurance and housing costs. She largely steered clear of national partisan politics, telling CNN’s Erin Burnett after polls closed that Mr. Trump was not a factor in her campaign — that she focused on her opponent and “issues that matter most to Florida families.”
“Everyone is feeling that affordability crisis, and the last thing that Florida families needed when they’re struggling is $4 gas,” she said.
Her path to the ballot wasn’t without controversy. When the seat was vacated in August after Republican incumbent Mike Caruso resigned to become Palm Beach County clerk and comptroller, nearly two months passed before Gov. Ron DeSantis scheduled the special election — a delay that prompted Ms. Gregory to file a lawsuit arguing voters were being denied representation in Tallahassee. Her campaign also drew criticism in its final stretch over a political mailer that some argued contained racially charged imagery and misleading claims about Mr. Maples’ residency.
The victory and its significance
District 87, which covers Jupiter, Palm Beach Gardens, Riviera Beach, Juno Beach and parts of Lake Worth Beach, had not been represented by a Democrat since at least 2000. Mr. Caruso had won reelection there by 19 percentage points in 2024, and Mr. Trump carried the district by roughly 9 points that same year. Florida Democratic Party chair Nikki Fried said the result represented a nearly 11-point swing to the left.
The race also drew attention after it emerged that Mr. Trump had voted by mail in the contest — despite publicly criticizing the practice as “mail-in cheating” and backing the Republican-supported SAVE America Act, which would eliminate no-excuse mail-in voting. White House spokesperson Olivia Wales called the matter “a non-story,” noting the president is a Palm Beach resident who participates in Florida elections.
Mar-a-Lago will now be represented by Democrats in the Florida state House, Senate and U.S. House — though Republicans retain overall control of all three chambers. District 87 is the 10th GOP-held state legislative seat Democrats have flipped nationally since Mr. Trump returned to the White House.
“When we started this, nobody thought it was possible. They thought we were crazy,” Ms. Gregory told supporters Tuesday night. “I knew my community. I knew we deserved better. We deserve a leader who will fight for us.”
Ms. Gregory is expected to be seated in the Florida House in early April and will seek election to a full two-year term in November.
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