Jon Maples launches new HD 87 bid, will retool strategy for November race

Less than a week after falling short in a Special Election for House District 87, Republican Jon Maples is regrouping and running it back.

Maples just filed to run for HD 87 again in November, by which time he hopes a retooled campaign strategy will deliver him a rematch win over Democrat Emily Gregory.

“I’m focused right now on making the case that I’m the best choice to represent our community in Tallahassee,” Maples told Florida Politics.

“We filed today, and I’m making the case to every voter starting right now. I’m not done.”

Maples, a financial planner and former Lake Clarke Shores Council member who earned All-American honors as a college athlete, said he and his campaign team are going to evaluate his Special Election performance to refine his game plan for the Midterm.

“I take full responsibility, and there will be some changes as we move forward now,” he said. “No question is not going to be asked. We’re looking at everything, and that means what I could have done better and what my team could have done better. We’re going to evaluate the situation line item by line item, tighten our belts, make it competitive and give the voters a reason why I’m a better fit to represent them in Tallahassee.”

As they did ahead of Election Day last Tuesday, Republican apparatuses at the local, state and federal levels are again lining up behind Maples as their preferred GOP candidate.

House Speaker-designate Sam Garrison of Fleming Island called Maples “a fighter” and confirmed he has the Florida House Republican Campaign Committee’s (FHRCC) full endorsement.

“His support for a strong economy, safe streets, and quality schools is the exact kind of common-sense, conservative leadership we need in the Florida House,” Garrison said in a statement. “The FHRCC is proud to support Jon’s campaign all the way through to victory in November.”

Republican Party of Florida Chair Evan Power praised Maples’ “commonsense, business-minded approach to state government,” which he said will be a boon to state policymaking.

“Jon is a great candidate for HD 87 as he is passionate about serving the community and ensuring every child has the opportunity to succeed,” he said in a statement. “An American Dream success story, he knows what it takes to make Palm Beach work for all families.”

Maples entered Tuesday as many political observers’ favorite to win the Special Election for HD 87, a coastal Palm Beach County district that includes President Donald Trump’s Mar-a-Lago home.

But Gregory, a first-time candidate, won in an upset, becoming the first Democrat to take the Republican-leaning district that Trump and former Republican Rep. Mike Caruso won in 2024 by 9 and 19 points, respectively.

While Maples led with Election Day and early, in-person voting, Gregory received significantly more mail-in ballots — a voting method Trump has frequently criticized despite repeatedly using it himself.

Questions about the election result arose over the weekend, following the arrest of a Democratic election volunteer whom authorities accused of stealing voting equipment days before the March 24 Special Election.

Investigators say an encrypted access key the man allegedly took was solely for training databases, but some officials have suggested the key could be reverse engineered to access live voting systems.

The Republican Party of Florida said in a statement that it expects a “full, thorough investigation.” Maples said the same.

“Election security is a major concern, but I do have faith that it will be fully investigated by law enforcement,” he said. “Voters should have 100% confidence in our election, and questions remain about the outcome of my race. That tells me there’s more work to do in the election-integrity department.”

Maples acknowledged other issues with this month’s Special Election. In the race’s home stretch, Gregory’s campaign drew criticism for a political text that some argued featured racially charged imagery and misleading claims about his residency and voting record.

Maples called the text “distasteful at best,” but said he resisted responding in kind because “that isn’t who I am.”

“This isn’t always easy. You get beat up, oftentimes, but you have to continue to do what you know is right. People wanted me to retaliate,” he said.

“I just wasn’t going to respond, because the moment I respond to something like that, people begin to think, ‘Oh, we just do this and you’ll respond and do all those things.’ No, I’m not doing that. Was it wrong? Yes. But what can I do? I’d rather them be making fun of me than my family. That’s what I signed up for, so it is what it is.”

HD 87 runs up the coast through Palm Beach Gardens, Jupiter, Juno Beach and Hypoluxo. Prior to Gregory’s win, the district trended reliably Republican in recent cycles.

Across Palm Beach County, Democrats have a narrow but shrinking voter lead of about 13,000. Statewide, Republicans continue to hold a significant registration advantage — a 1.48 million-voter edge as of last month.

Gregory said Monday that she believes her upset win could be a blueprint for other Democrats, who she said “are on the right side of the issues” and “have the momentum.”

Also on Monday, the Democratic National Committee announced the launch of its first-ever Midterm-year partisan voter registration effort in Florida and debuted a new playbook to guide operational best practices for candidates and staff.

Many eyes will be on HD 87 in the coming months.