HD 87 voters to fill long-vacant seat as Emily Gregory, Jon Maples face off in Special Election

Voters in House District 87 head to the polls Tuesday to choose between Democrat Emily Gregory and Republican Jon Maples in a Special Election to fill a legislative seat left vacant for seven months.

The Palm Beach County district — which runs up the coast through Palm Beach Gardens, Jupiter, Juno Beach and Hypoluxo — has gone without representation since August, when Republican state Rep. Mike Caruso resigned to become the county’s 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.

HD 87 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.

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.

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, has run a campaign closely aligned with Republican priorities at both the state and national levels.

He has 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 focuses on cutting taxes and government spending, reducing regulatory burdens, expanding private-sector job growth and advancing school choice policies.

He has also embraced a broader GOP push to eliminate or significantly reduce property taxes and has sought to draw contrasts with Gregory on education policy, particularly around teachers’ unions.

Maples heads toward 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 total haul has since grown to $440,000, he told POLITICO, which reported that Maples’ spending on digital and TV ads nearly topped $100,000.

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.

Maples’ campaign faced questions in its final stretch regarding his residency. Reporting this month noted his listed home sits outside HD 87 and that he registered to vote at an in-district apartment in January. He has since said that he and his family recently 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, a 40-year-old first-time candidate, has framed her campaign around affordability and local quality-of-life concerns.

She’s a South Florida native who 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 centers on increasing public education funding, expanding access to health care and addressing rising property insurance and housing costs.

She has drawn a sharp distinction with Republicans on tax policy, opposing efforts to eliminate property taxes, which she argues would shift the burden onto renters through higher sales taxes and local fees.

At the same time, Gregory has 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.

Democrats have 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.

Last week, the Florida GOP celebrated flipping two municipal seats in the county. At the same time, Democrats touted the victory of Andy Thomson, who became the first person to turn the Boca Raton mayoralty blue in at least 45 years following a razor-thin race.

Maples remains the favorite on paper, due to his larger war chest, political experience, advertising activity and the organizational support he enjoys from an increasingly powerful state party already dominating the Capitol. The district has notably reddened in recent years; in 2020, Trump took HD 87 by 0.1 percentage points. Four years later, he won it by 10.6 points, according to Matt Isbell of MCI Maps.

Still, Special Elections are often less predictable than general contests, and turnout plays an outsized role. Considering less than 10% of the registered voters in HD 87 cast ballots in the Primary, Tuesday’s outcome could prove surprising.