President Donald Trump’s Mar-a-Lago property in Palm Beach, Florida.
Marco Bello | Reuters
Emily Gregory, a small business owner and first-time candidate, is aiming for an upset in Tuesday’s special election for a Mar-a-Lago seat in the Florida House of Representatives.
Gregory is a Democrat running for the state’s 87th Congressional District, which stretches along the southeastern coast of Florida, including Palm Beach, President Donald Trump’s home and resort, as well as South Palm Beach and Juno Beach.
“This is the kind of district that fits right outside the bubble of Democratic overperformance in targeted campaigns that we’ve seen in the past,” Heather Williams, chair of the Democratic Legislative Campaign Committee, said in an interview with reporters from CNBC and MS Now. “There’s a chance we can win. I wouldn’t be surprised if we don’t.”
Gregory is facing Trump-backed candidate John Maples, a financial advisor and former college basketball player, in a district that has been held by Republicans since 2022.
Republican Mike Caruso, who represented the area in the state Legislature until resigning in 2025, won reelection in the 2024 election by a 19-point margin. But with President Trump’s approval ratings declining and Democrats across the country making gains in special elections, Mr. Gregory and his allies see an opportunity to play spoiler and potentially win a seat with great symbolic value.
But Gregory said Trump is not the focus.
“It influenced what people were willing to talk to me about,” Gregory said in an interview. “He’s a voter. But I’m more focused on all of the 115,000 voters in the 87th District, not just one of them.”
However, in the MAGA era, President Trump has significantly reduced his numbers in some state and local elections, especially those in which the president has a personal stake. In January, Trump endorsed Maples, who vacated her seat on the Lake Clark Shores City Council last year.
Mr. Maples did not respond to repeated calls to the financial advisor’s office. His campaign did not respond to multiple emailed requests for comment. The Florida Republican Party did not respond to an emailed request for comment.
“As your next state representative, John will work tirelessly to grow our economy, lower taxes and regulations, promote MADE IN THE USA, stop crime on immigration, protect our elections, support our military, veterans, and law enforcement, and protect the Second Amendment, which is always under siege,” the president wrote in a January post on Truth Social.
Trump became a resident of Florida in 2019, during his first term as president.
Mr. Maples describes himself as a “conservative outsider. America’s first patriot.”
Maples says on his campaign website that he will focus on “congested roads, polluted waterways” and “affordability challenges, from inflation to rising insurance costs and ever-increasing property taxes.” After acknowledging Trump’s endorsement, Maples called the president “the most transformational leader I have ever seen in my life” in a social media post.
“From liberating Venezuela to the incredible trade deals he is negotiating to securing our southern border after four years of open borders, the positive impact of his presidency will be felt for generations. America is better off with Donald J. Trump in the White House,” Maples wrote on Instagram.
Affordability as an issue in state elections
Gregory is passionate about speaking about issues of affordability. He said he would focus on addressing the state’s property insurance crisis and concerns about rising health insurance costs with the expiration of Affordable Care Act tax subsidies earlier this year. He said the state Legislature should expand Medicaid, stop watering down public education and focus more on food issues.
“Congress is focused on attacking vulnerable communities and engaging in culture wars, not solving the affordability crisis in our state,” Gregory said.
But it will be an uphill climb for Mr. Gregory to win Tuesday in a state where Republicans have a financial advantage and more than 1 million more Democratic registered voters.
Mr. Gregory is pinning his hopes on the national trend of overwhelming Democratic wins in last year’s special elections, including in ruby-red Florida.
According to local media outlet MCI Maps, in Florida’s nine special elections in 2025, Democrats outperformed 2024 Democratic presidential candidate Kamala Harris, in some cases by double digits. And in December, Eileen Higgins became the first Democrat to win Miami’s mayoral race in nearly 30 years.
“We knocked on every door and made every call. I’m really proud of the campaign we ran. I think it’s close, and I think we’ll be on the right side,” Gregory said.
