Trump’s next Florida rep could be 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 — 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…