Trump's Backyard Just Went Blue

Emily Gregory's upset in Florida House District 87 signals something Republicans are going to have a hard time explaining away.

Donald Trump voted by mail in Tuesday's special election for Florida House District 87. He voted for Jon Maples, the 43-year-old financial adviser and Trump-endorsed Republican running to hold the Palm Beach County seat. Maples lost anyway. The district, which runs along the coast through Palm Beach Gardens, Jupiter, Juno Beach, and Hypoluxo, includes Mar-a-Lago, where the president of the United States claims legal residency. That district is now represented by a Democrat.

Emily Gregory, a 40-year-old first-time candidate who owns and operates a Jupiter-based fitness center for pregnant and postpartum women, defeated Maples 51.15% to 48.85% in the final tally, pulling in 17,047 votes to his 16,281. This special election was Gregory's inaugural run for public office. She won in a district that Trump carried by roughly 9 percentage points in 2024, where incumbent Republican Mike Caruso won his last re-election by nearly 20 points.

The seat opened up after Caruso resigned in August 2025 when Gov. Ron DeSantis appointed him Palm Beach County Clerk of the Circuit Court and Comptroller. Under Florida law, DeSantis was responsible for calling a special election to fill the vacancy. He waited nearly two months to do so, long enough that Gregory filed a lawsuit arguing voters were being denied representation in Tallahassee during the 2026 legislative session. DeSantis eventually called the election. The lawsuit became moot. The seat still flipped.

Republicans pulled serious weight into this race. Rep. Byron Donalds, currently running for Florida governor, made campaign appearances alongside Maples. Florida Attorney General James Uthmeier endorsed him. Trump himself praised Maples at a Florida event the Saturday before the election, calling him up on stage. Then Trump mailed in his ballot, which Palm Beach County voter records confirmed was counted. Democrats brought in the Democratic Legislative Campaign Committee, retired Lt. Col. Alex Vindman held a virtual fundraiser for Gregory, and former Rep. Lois Frankel endorsed her campaign. Gregory's campaign was not without controversy either. A political text attacking Maples circulated in the days before the election, featuring what some criticized as racially charged imagery and misleading claims about his residency and voting record. The message was tied to a political committee with connections to Gregory's campaign vendor.

Florida Democratic Party Chair Nikki Fried called Gregory's win a nearly 11-point leftward swing in the district. Since Trump returned to the White House in January 2025, Democratic candidates have flipped 29 Republican-held seats in state legislatures across the country. HD 87 is the latest. The DLCC described it as a "rare flip opportunity" even against a Republican Party that holds a 1.48 million-voter registration edge statewide and a shrinking but persistent Democratic advantage of roughly 13,000 voters across Palm Beach County.

Gregory is expected to pursue a full two-year term in November. She will be sworn in between April 1 and April 4, at which point she will formally represent, among others, the sitting president of the United States.

The man who spent years telling Americans that mail-in voting was a corrupt, fraudulent system mailed in his ballot for a candidate who lost by 766 votes in his own neighborhood.

@Santitos

@salinasmariasantos

Copyright © 2026 Maria Santos Salinas for FRONTeras.

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