It looks like President Donald Trump will be represented by a Democrat in the Florida House.
Emily Gregory flipped House District 87 in Palm Beach County blue in an upset victory. With most votes totaled, she held a lead outside the recount margin. It marks the first time a Democrat has won there this century.
Gregory won 51.15% of the vote Tuesday to Republican Jon Maples’ 48.85% in a race where controversies arose for both candidates in the leadup to Election Day.
She fills a seat Republican Mike Caruso left vacant in August, when he left for an appointed job as Palm Beach County Clerk and Comptroller.
The extended vacancy became a defining issue in the race itself. Nearly two months passed before Gov. Ron DeSantis called the election in late October, a delay that prompted Gregory to sue, arguing voters were being denied representation.
While the lawsuit became moot once DeSantis scheduled the contest, the lag meant residents had no voice in Tallahassee during the 2026 Legislative Session.
The race in days leading up to the Special Election garnered national attention, thanks to a perception it was the most likely red-to-blue flip among three legislative Special Elections in Florida on Tuesday. It also drew press when Trump cast his ballot through the mail.
HD 87 — which runs up the coast through Palm Beach Gardens, Jupiter, Juno Beach and Hypoluxo — has trended reliably Republican in recent cycles. Caruso won re-election by 19 percentage points in 2024, when President Donald Trump carried the district by roughly 9 points.
Democrats nationally celebrated the victory in the President’s back yard.
“Donald Trump’s own neighbors just sent a crystal clear message: They are furious and ready for change,” Democratic National Committee Chair Ken Martin said in a statement.
“While Trump is partying with his billionaire donors and building gilded ballrooms, Americans are being left behind and raising hell with their votes. Rep.-Elect Emily Gregory ran an incredible campaign focused on Florida families’ top concerns, from the skyrocketing cost of groceries and gas to the health care crisis Donald Trump has unleashed across Florida. If Democrats can win in Trump’s own backyard, we can win anywhere. From now until November, Democrats are all gas and no brakes as we compete across every corner of Florida and the nation.”
“Mar-a-Lago just flipped red to blue, which should have Republicans sweating the midterms. A Trump +11 district in his own backyard shouldn’t be in play for Democrats, but tonight proves Republicans are vulnerable everywhere. State Democrats have now flipped a staggering 29 districts red to blue since Trump’s election. Gas prices are spiking, grocery costs are up, and families can’t get by – it’s clear voters at the polls are fed up with Republicans,” said Democratic Legislative Campaign Committee President Heather Williams
“If Mar-a-Lago is vulnerable, imagine what’s possible this November. Democrats are clearly on offense as we prepare for the most expansive midterm strategy ever down-ballot, with 650 seats in play. 2026 is shaping up to be an election for the history books.”
And House Democratic Leader-Designate Christine Hunschofsky cheered growing party ranks in Tallahassee.
“Emily proved that Floridians are ready for change and ready for leaders who will focus on delivering real results that help bring down everyday costs for working families,” she said, “We could not be more excited to welcome Representative Gregory to the House Democratic Caucus, where her voice will be critical as we head into upcoming Special Sessions on redistricting and passing the state budget.”
Both Gregory and Maples advanced to the General Election after overwhelming Primary wins in January, each securing more than 80% of the vote in their respective contests.
Gregory, a 40-year-old South Florida native and first-time candidate, framed her campaign around affordability and local quality-of-life concerns.
She grew up in nearby Stuart and today owns and operates a small Jupiter-based fitness center for pregnant and postpartum women. She is also an Army spouse.
Her platform centered on increasing public education funding, expanding access to health care and addressing rising property insurance and housing costs.
During her campaign, she drew a sharp distinction with Republicans on tax policy, opposing efforts to eliminate property taxes, which she argued would shift the burden onto renters through higher sales taxes and local fees.
At the same time, Gregory signaled openness to more targeted relief, such as exemptions for first-time homebuyers.
Gregory criticized the GOP-led Legislature’s focus on curbing diversity, equity and inclusion programs, arguing that such efforts eschew more pressing economic challenges facing residents.
Her campaign reported raising about $176,000 directly, supplemented by roughly $82,000 in in-kind support. She has said her total fundraising reached $325,000 with additional help from a political committee.
Her endorsements include U.S. Rep. Lois Frankel, Florida Senate Democratic Leader Lori Berman and several local officials, as well as backing from a passel of labor groups and progressive organizations. She also received a boost from a recent virtual fundraiser hosted by Alex Vindman, the whistleblower behind Trump’s first impeachment now running to supplant Republican U.S. Sen. Ashley Moody, and congressional candidate Pia Dandiya, who is running to unseat Republican U.S. Rep. Brian Mast.
The win grows a Democratic caucus in the House, a welcome development to House Minority Leader Fentrice Driskell even late in the legislative term.
““I could not be more excited to welcome Representative Emily Gregory to the House Democratic Caucus!” Driskell said. “Floridians have made it clear they want real action on the affordability crisis and while Republicans have ignored them. Emily ran a campaign focused on pragmatic solutions to lower costs, raise wages, and build a more affordable state for all working families and seniors that resonated with the people of Palm Beach County. We look forward to her joining us in Tallahassee as we continue to fight for our affordability agenda to provide Floridians with the relief their hard work has earned.”
Maples, a 43-year-old financial planner and former Lake Clarke Shores Council member who was an All-American athlete at Palm Beach Atlantic University, ran a campaign closely aligned with Republican priorities at both the state and national levels.
He leaned on his local government experience and community involvement, including leadership roles with Families First of Palm Beach County and other civic organizations.
His platform focused on cutting taxes and government spending, reducing regulatory burdens, expanding private-sector job growth and advancing school choice policies.
He also embraced a broader GOP push to eliminate or significantly reduce property taxes and sought to draw contrasts with Gregory on education policy, particularly around teachers’ unions.
Maples headed to Election Day with a sizable financial and institutional edge. Through mid-February, he raised $290,000 in outside contributions, which he added to $14,000 in self-loans through his campaign account and political committee, Friends of Jon Maples.
His haul grew further to $440,000, he told POLITICO, which reported that Maples’ spending on digital and TV ads had nearly topped $100,000 in the election’s home stretch.
Maples’ campaign also benefited from significant outside support, including roughly $184,000 in in-kind assistance from the Florida House Republican Campaign Committee (FHRCC).
His endorsement list reflects that backing. Trump, Attorney General James Uthmeier and a slew of GOP state lawmakers that includes Florida Speaker-designate Sam Garrison and state Reps. Anne Gerwig, Jon Snyder and “MAGA” Meg Weinberger are backing Maples, as are Lake Worth Beach Commissioner Mimi May and former state Rep. MaryLynn Magar.
Questions arose in recent weeks regarding his residency, with reporting this month noting his listed home sat outside HD 87 and that he’d registered to vote at an in-district apartment in January.
He has since said he and his family bought and moved into a new home in Jupiter within the district’s bounds.
Under Florida law, candidates must only live in the district they seek to represent by the time they are sworn in — which, in this case, is expected between April 1 and April 4.
Gregory’s campaign drew criticism last week for a political text attacking Maples that some argued featured racially charged imagery and misleading claims about his residency and voting record.
The message was linked to a political committee with ties to Gregory’s campaign vendor, raising questions about coordination.
Democrats characterized the HD 87 race as a “rare flip opportunity,” even as Republicans continue to hold a significant statewide registration advantage — a 1.48 million-voter edge statewide as of last month.
Across Palm Beach County, Democrats have a narrow but shrinking voter lead of about 13,000.
Florida Democratic Party Chair Nikki Fried said the win would power the party into the Midterms.
“I’m thrilled to congratulate Representative-Elect Emily Gregory on this monumental victory. A nearly 11 point swing to the left in this hard fought race shows the impact of Democrats’ long-term investment in Florida, and now the people of HD 87 will have a champion in Tallahassee,” Fried said.
“This victory reiterates an undeniable trend in Florida: with year round organizing and infrastructure investment, Democrats can run and win anywhere–including Donald Trump’s backyard. Floridians are tired of the chaos, corruption, and sky high prices on everything from groceries, to gas, and healthcare. They are voting for trusted leaders like Emily to steady the ship and return common sense, people-centered solutions back to our communities.”
Locally, Democrats in Palm Beach County also saw the moment as a turn in fortune.
“The Palm Beach County Democratic Party is thrilled that Emily Gregory has won a seat in the Florida House and will be representing her constituents in District 87,” said Palm Beach County Democratic Party Chair Howard Richman.
“This success was only possible through a seamless partnership between the Gregory campaign, the Florida Democratic Party, and the tireless local organizers of the PBC Democratic Party. We want to recognize the incredible dedication of our local volunteers: those of you who spent hundreds of hours knocking on doors, making calls, and mobilizing your neighbors were the true engine of this win. Together, we are sending Emily to Tallahassee to protect renters and homeowners, fix healthcare, and rebuild public education.”
And U.S. House Minority Leader Hakeem Jeffries suggested the win signaled a blue wave in November, when Democrats hope to take back a majority in the U.S. House.
“Democrats FLIPPED a state House seat in Palm Beach that Trump won by 11 points in 2024,” the New York Democrat said. “Mar-a-Lago will now be represented by Emily Gregory, a strong Democratic voice. We will crush House Republicans in November if (Gov. Ron) DeSantis tries to gerrymander the Florida congressional map.”
___
Jacob Ogles contributed to this report
