Trump’s next Florida rep could be Democrat Emily Gregory

Emily Gregory, a small business owner and first-time candidate for elected office, is looking to score an upset in a Florida special election on Tuesday to represent Mar-a-Lago in the state legislature.

Gregory is a Democrat running for state House District 87, which runs up the coast of southeast Florida and includes Palm Beach — where President Donald Trump’s home and resort is located — as well as South Palm Beach and Juno Beach.

“It is the kind of district that fits just kind of outside the bubble of what we’ve seen Democratic over-performance in these targeted races,” Heather Williams, president of the Democratic Legislative Campaign Committee, said in an interview with journalists from CNBC and MS Now. “We could win it. If we don’t win it it’s not going to be a surprise.”

Gregory is squaring off against Trump-endorsed candidate Jon Maples — a financial advisor and former college basketball player — in a district the GOP has controlled since 2022.

Republican Mike Caruso, who represented the area in the state House until his resignation in 2025, won reelection in 2024 by 19 points. But as Trump’s approval ratings dip and Democrats throughout the country are showing gains in special elections, Gregory and her supporters see an opportunity to play spoiler and potentially pick up a seat with major symbolic value.

But according to Gregory, Trump is not the focal point.

“It’s impacted people’s interest in talking to me about it,” Gregory said in an interview. “He is a constituent. But I am more focused on all 115,000 voters in District 87, not just the one.”

But in the MAGA era, Trump cuts a large figure even in some state and local races, particularly ones where the president has a personal stake. In January, Trump endorsed Maples, who last year stepped away from his seat on the Lake Clarke Shores Town Council.

Maples did not respond to multiple phone calls to his financial advisory office. His campaign did not respond to multiple emailed requests for comment. The Republican Party of Florida did not respond to an emailed request for comment.

“As your next State Representative, Jon will fight tirelessly to Grow the Economy, Cut Taxes and Regulations, Promote MADE IN THE U.S.A., Stop Migrant Crime, Safeguard our Elections, Support our Military, Veterans, and Law Enforcement, and Defend our always under siege Second Amendment,” the president wrote in a post to Truth Social in January.

Trump became a Florida resident in 2019, during his first term as president.

Maples has branded himself a “conservative outsider. America First patriot.”

On his campaign website, Maples says he would focus on “congested roads, polluted waterways” and “affordability challenges, from inflation to soaring insurance premiums to ever-increasing property taxes.” After notching Trump’s endorsement, Maples called the president “the most transformative leader I’ve seen in my lifetime” in a social media post.

“The positive impacts of his presidency will be felt for generations — from the liberation of Venezuela, to the incredible trade deals he’s negotiating, to securing the Southern Border after 4 years of open border policies. America is better off with Donald J Trump in the White House,” Maples posted to Instagram.

Gregory is eager to talk about affordability issues. She said she would be focused on addressing the state’s property insurance crisis and concerns about spiking health insurance costs with the expiration of Affordable Care Act tax subsidies earlier this year. She said the state legislature should expand Medicaid, stop gutting public education and focus more on kitchen table issues.

“The legislature is focused on attacking vulnerable communities and participating in culture wars and not solving the affordability crisis in the state,” Gregory said.

But Gregory has an uphill climb to win on Tuesday in a state where Republicans have a cash advantage and outnumber registered Democratic voters by more than a million. 

Gregory sees hopes in national trends of Democrats overperforming in special elections in the last year, including in ruby-red Florida.

Democrats outperformed 2024 Democratic presidential nominee Kamala Harris in nine special elections in Florida in 2025, in some cases by double digits, according to local outlet MCI Maps. And in December, Eileen Higgins became the first Democrat to win a mayoral race in Miami in nearly 30 years.

“We’ve knocked all of the doors, we’ve made all of the calls. I’m really proud of the campaign we ran. I think it’s going to be close, and I think we’re going to come out on the right side of it,” Gregory said.