The Local Special Election Sparking Intrigue In Donald Trump’s Backyard

Florida Democrats are trying to flip the Palm Beach state House district that includes Mar-a-Lago this month, in a race that could test President Donald Trump’s Sunshine State influence and symbolically hit him on his home turf.

A Democratic win on March 24 in the District 87 special election would embolden Florida’s beleaguered Democratic Party ahead of the midterms and add to a string of recent nationwide victories and overperformances. After a slew of losses in recent cycles, Florida Democrats in particular have tried to show they can return the state to swing status and end the Legislature’s GOP supermajority in November.

And in the district hosting Trump’s home and private club, the symbolism of a Democratic win could be overshadowed by a broader signal that Democrats have a chance to expand their midterm opportunities — across Florida’s gubernatorial and Senate races as well as nationwide.

Trump endorsed the Republican candidate in the race, former Lake Clarke Shores council member and financial planner Jon Maples. He’s up against Emily Gregory, a first-time candidate with a background in public health and mental health administration who now runs a fitness center for postpartum moms. The seat became available in August 2025 after Gov. Ron DeSantis appointed the former officeholder, Republican Mike Caruso, as the Palm Beach County clerk and comptroller.

DeSantis waited months to call a special election and announced it in October after Gregory sued over the delay.

Maples, a former All-American basketball captain at Palm Beach Atlantic University, likened the president’s surprise endorsement for him to reaching the “big moment” in a game — one that requires “tenacity and just a fearless effort to get it done.”

“In those big moments, athletes have to rise to that occasion,” he said. “And when you get the endorsement of the president, it's a call to rise to the occasion.”

Despite the endorsement and district’s conspicuous location, Trump isn’t a centerpiece of either campaign in a race both candidates concede is rooted in concerns about affordability. Still, national issues have crept into the race, especially since Trump spends weekends at the “Winter White House." Gregory said residents have complained about congestion and a new flight path that avoids Mar-a-Lago. And Democratic Senate candidate Alex Vindman, who helped trigger Trump's first impeachment, held a virtual fundraiser for Gregory on Thursday night.

Anti-Gregory mailers viewed by POLITICO show the state House’s GOP campaign arm arguing residents “can’t afford” to elect a Democrat and linking the race to the president by contrasting pricing on certain foods and gas during the Biden administration with where it is under Trump.

“Floridians are fired up and ready to elect President Trump’s endorsed candidate, Jon Maples, because they know he will fight for the president’s America First agenda and help keep Florida the best place to live, work and raise a family,” said Republican National Committee spokesperson Emma Hill, responding to an inquiry about the race POLITICO sent to the White House.

The seat’s partisan lean has shifted over time, depending on its boundaries, and Caruso won reelection there in 2024 by 19 points. In 2024, Trump won the district by more than 9 points. Yet Palm Beach County leans Democratic; it’s represented by Democrats Lois Frankel in the U.S. House and Lori Berman in the state Senate. Berman is also the upper chamber’s minority leader.

But Republicans have narrowed the registration gap in Palm Beach County to 13,000, and GOP state party Chair Evan Power predicted they would overtake Democrats before the midterms. On Tuesday, Republicans flipped two local area seats. More broadly, Republicans hold a nearly 1.5-million voter advantage statewide.

Power said he thought Maples was in a “great position” to win the seat and called Democrats’ push a “continued search for relevance.”

“Obviously, they are going to try to score what they think is a political win wherever they can,” he said.

Official spending on the race won’t be public until the April 10 filing deadline, but what candidates are sharing so far indicates the race is seen as competitive. Gregory shared that her campaign and political committee raised $325,000, while Maples’ campaign and political committee said he raised more than $440,000. Maples and supporting groups spent $99,000 on digital and TV ads, with nearly $32,000 of it coming after the primary, data from the ad tracking firm AdImpact shows. No TV ad spending was reported for Gregory.

Florida Democratic Party Chair Nikki Fried said the state party was backing Gregory “with everything we’ve got” and made the race a top priority by sending staff and volunteers to knock on doors, make calls and send texts to ensure voters “flip the president’s home district.”

The district has been without representation throughout the Legislature’s regular session, which was scheduled to end Friday but has been defined by GOP scraps over policy and budget. Whoever wins the special election will join lawmakers as they deliberate on new congressional maps during a special session in April and possibly another on property taxes.

Gregory said she would “absolutely be a vote against mid-decade redistricting” and has talked about a property tax cut as a “tax shift” that could cause sales taxes to increase. She also said she would consider “targeted relief" on property taxes, including for first-time homebuyers.

Maples supports DeSantis’ push to abolish property taxes on primary homes, saying his experience working on finances makes him qualified for the job. On redistricting, he said he wants to see the forthcoming details before making any commitment.

“I need more data to understand what's happening, what the changes are,” he said.

Gregory pointed to measures passed during this year’s session — including a ban on diversity, equity and inclusion in local governments — as a sign that the Legislature had the wrong priorities. She argued “people love their Lake Worth Pride Parade” and would view such measures as overreach and part of a pattern that shied away from addressing affordability. The military spouse and mom of three also said property insurance ranks at the top of people’s concerns and that she would support measures such as capping premium rate hikes.

“Since the Republicans gained a supermajority four years ago, we have not seen any of the affordability crisis issues, any of the housing — anything that would bring real relief to Florida families," she said. "And it feels like every session is more targeted on harming Florida families and vulnerable populations.”

Maples, a father of one who’s married to a teacher, touted his support for Florida’s universal school voucher program during an interview. In mailers, the state House’s GOP campaign arm has been hammering Gregory as a “partisan liberal” who “embraces the teacher’s union.” The mailers quote Gregory saying that "vouchers should be a lifeline for families who need them most, not a back door to undermine public schools."

Low turnout is often a challenge for special elections, leaving the candidates not only with the job of selling themselves, but also ensuring voters understand a race is happening. In this case, Maples said, some voters conflated Tuesday’s municipal races with the special election in 11 days. Whoever wins will also need to quickly launch a reelection campaign for the November 2026 race.

State Rep. Sam Garrison, the Republican next in line to be House speaker who’s in charge of shepherding state House races for the caucus, acknowledged in an interview at the Florida Capitol that a special election “provides challenges” but said the party was “working extraordinarily hard.” He praised Maples as part of “central casting,” and someone who “understands business, understands finance and is a perfect fit for his district.”

His Democratic counterpart, Leader-designate Christine Hunschofsky, said the lower chamber was “optimistic” about the election and praised Gregory as someone who understands voters “deserve a voice to provide practical solutions on the issues that matter.”