Florida Special Election Could Deliver Democratic Representative for Trump's Mar-a-Lago Neighbourhood
President Donald Trump could soon find himself with a Democratic state representative in his own backyard as voters in Florida's House District 87 head to the polls for a special election on Tuesday.
Democrat Emily Gregory, a 40-year-old mother of three and small business owner, is hoping to pull off an upset victory against Republican Jon Maples, 43, who has received Trump's personal endorsement.
Vacant Seat Creates Opportunity
The special election was called to fill the state House seat vacated by Republican Mike Caruso, who was appointed by Florida Governor Ron DeSantis last summer to serve as county clerk and comptroller. The seat has remained empty since August, creating an unexpected opportunity for Democrats in a district that has traditionally leaned Republican.
If Gregory succeeds, it would represent a significant embarrassment for Trump, who changed his primary residence to Mar-a-Lago in 2019 during his first term. The exclusive club and estate sits squarely within the boundaries of House District 87.
Candidate Backgrounds and Controversies
Emily Gregory has leveraged her background in health and exercise science to build a successful small business, FIT4MOM Palm Beach, which offers specialised exercise classes for pregnant women and new mothers. She has also highlighted her experiences as a military spouse during her campaign.
The Palm Beach Post, the region's leading local newspaper, endorsed Gregory on Monday, giving her campaign a significant boost ahead of the election.
Her opponent, Jon Maples, received Trump's endorsement ahead of the January primary, with the former president describing him as a "very successful Businessman and Civic Leader" who would fight for economic growth, tax cuts, and support for military and law enforcement.
Residency Questions and Legal Requirements
The Florida Democratic Party has raised questions about Maples' residency, alleging that during the January primary he was using a voter registration address associated with a motel in Palm Beach Shores. The party claims this same address was used again in March and has called on Maples to withdraw from the contest.
Florida Politics reported that Maples has since stated he and his family have moved into a home in Jupiter, Florida, which falls within the district boundaries. Under Florida law, a representative only needs to establish residency in the district at the time of their swearing-in, not during the election campaign.
Political Landscape and Democratic Optimism
While the district has generally trended Republican—Trump won it by approximately nine points in the last presidential election, and Caruso secured victory by nineteen points—Democrats believe the seat could be flippable in a special election.
Maples maintains a fundraising advantage over Gregory, and Republicans still hold a statewide voter registration edge. However, Democrats point to recent successes in nearby races, including the election of Democrat Andy Thomson as mayor of Boca Raton, the city's first Democratic mayor in forty-five years.
The election has gained additional attention due to Trump's own voting method. The New York Times reported that the president voted in the special election by mail, despite having previously referred to mail-in voting as "mail-in cheating."
As voters prepare to cast their ballots, the outcome could signal shifting political dynamics in a region that has become symbolic of Trump's post-presidency life and political influence.
