Democrat Wins Special Election in Trump's Mar-a-Lago District

On March 24, 2026, Emily Gregory, a 40-year-old fitness center owner and first-time candidate, won a special election for Florida House District 87—the Palm Beach County seat whose constituents include President Donald Trump himself. Gregory defeated Jon Maples, a 43-year-old financial adviser endorsed by Trump, by a margin of 51.15% to 48.85%, flipping a district Republicans had held for decades [1][2].

The result carries symbolic weight: Trump voted in this election, casting a mail-in ballot that Palm Beach County records confirm was counted [3]. His endorsement of Maples—"JON MAPLES HAS MY COMPLETE AND TOTAL ENDORSEMENT!"—did not carry the day [4]. The district includes Mar-a-Lago, the president's private club and de facto second seat of government.

But beyond the symbolism, the race fits into a broader and more consequential pattern. Since Trump returned to the White House in January 2025, Democrats have flipped at least 29 state legislative seats nationwide from Republican control. Republicans have flipped zero [5][6].

The Numbers: A 30-Point Swing

The scale of the shift in HD-87 is striking. In November 2024, Republican incumbent Mike Caruso won reelection by roughly 19 percentage points [7]. Trump carried the district by approximately 11 points in the presidential race that same year [3]. In the March 2026 special election, Gregory won by 2.3 points—a swing of more than 20 points from the last state House result and roughly 13 points from Trump's own performance in the district [1][2].

Turnout was 28.82%, with 33,470 ballots cast from 116,128 registered voters [8]. As of election morning, Democrats had cast 7,457 early and mail ballots to Republicans' 7,176, with voters registered to no party accounting for more than 2,800 [9]. That narrow Democratic edge in early voting, combined with Gregory's performance among independents and her apparent ability to peel off some Republican voters, produced the upset.

The district had been in Republican hands continuously this century. Caruso first won it in 2018 by just 32 votes—a margin so thin it triggered both machine and manual recounts [10]. He went on to build large margins in subsequent cycles before resigning in August 2025 to become Palm Beach County clerk and comptroller, triggering the special election [1].

Source: Florida Division of Elections / AP

Data as of Mar 25, 2026CSV

Who Won and Why: A Grassroots Campaign vs. Party Infrastructure

The two candidates offered a study in contrasts—not just on policy, but in how they built their campaigns.

Gregory, a South Florida native who grew up in nearby Stuart, owns a Jupiter-based fitness center for pregnant and postpartum women. She is an Army spouse with no prior political experience [4][11]. Her campaign raised $389,822, powered by more than 4,500 individual contributions during the final reporting period alone, most under $50 [12]. The Florida House Democratic Campaign Committee contributed $30,000, the Florida Democratic Party $3,000, and the Florida Democratic Legislative Campaign Committee $10,000, with an additional $4,000 in in-kind party support [12].

Maples, a former Lake Clarke Shores council member and financial adviser, raised $276,208 in direct campaign contributions, including a $14,000 personal loan [12]. But the Republican institutional apparatus invested far more heavily: the Florida House Republican Campaign Committee and the Republican Party of Florida provided $204,795 in in-kind support. A separate political committee, Friends of Jon Maples, raised $115,300 and spent $39,342 [12]. In total, roughly $397,840 in outside support was tied to Maples's candidacy [12].

The spending totals tell a story: more than $1 million flowed into a single state House race [12]. Gregory's money came overwhelmingly from small donors. Maples's came overwhelmingly from party committees and affiliated PACs. Gregory outspent Maples from her direct campaign account ($315,369 spent vs. Maples's lower direct spending), while Maples benefited from a larger institutional support network [12].

The Residency Problem

Maples entered the race burdened by a controversy that dogged him through election day. Public records showed he changed his voter registration address to a motel in Palm Beach Shores on January 12, 2026 [13]. Neighbors at the address said they never saw him move in, and the Florida Democratic Party filed a formal complaint with the Florida Department of State's general counsel and the Office of Statewide Prosecution, alleging residency violations [13][14].

Maples acknowledged recent moves to establish district residency while maintaining property elsewhere [15]. Under Florida law, state House candidates must reside in their district, but enforcement of this requirement has historically been inconsistent.

The residency issue provided Gregory with a tangible line of attack—that her opponent was a carpetbagger selected by party insiders rather than someone rooted in the community. Whether this was decisive is impossible to isolate, but it was a persistent vulnerability that Maples never fully neutralized.

Affordability: The Issue That Dominated

Both candidates agreed on one thing: the top concern they heard from voters was affordability [15]. The district spans coastal Palm Beach County, including Jupiter and Palm Beach Gardens—areas where the median home value countywide is $491,500 and median household income is $84,921 [16]. But those county-level figures obscure enormous variation. The Town of Palm Beach, where Mar-a-Lago sits, has a median household income of $168,403 and a median property value of $2 million [17]. The communities surrounding it—Lake Worth Beach, Hypoluxo, Lantana—are far more middle-class.

Gregory centered her campaign on property insurance reform, housing costs, public education funding, and healthcare access [4][11]. On insurance specifically, she advocated for a state catastrophic fund and caps on insurance company profits and rate hikes, though she acknowledged she would need more stakeholder input to develop specific proposals [15].

Maples proposed eliminating property taxes entirely, arguing it would save residents thousands of dollars. He said the state could maintain services through budget discipline: "We have to absolutely have the conversation realistically about tightening our own belt" [15]. On insurance, he supported continuing existing legislative reforms aimed at increasing insurer competition [15].

Gregory also framed the election around Republican priorities in Tallahassee. She argued that GOP lawmakers had prioritized culture war legislation over the economic concerns of everyday Floridians—a message that appeared to resonate in a district where bread-and-butter costs are a daily reality even for relatively affluent households [11].

The National Pattern: 29 Flips, Zero Republican Gains

HD-87 is not an isolated result. It is the latest in an unbroken streak of Democratic overperformance in special elections since Trump's second inauguration.

By mid-March 2026, Democrats had flipped at least 29 state legislative seats from Republican control across the country, in states including Iowa, Pennsylvania, Mississippi, Georgia, Texas, Arkansas, New Hampshire, and Florida [5][6]. Republicans had not flipped a single Democratic-held seat during the same period [5].

In 2025 alone, Democrats flipped 21% of all GOP-held seats that appeared on special election ballots—a rate exceeding even the 20% flip rate of 2017, which preceded the 2018 midterm wave that swept 40 U.S. House seats into Democratic hands [6].

Source: NBC News / DLCC / Bolts Magazine

Data as of Mar 25, 2026CSV

Within Florida specifically, the pattern has been consistent. Across nine special elections held in 2025 for congressional and state legislative seats, Democratic candidates ran an average of 17 percentage points ahead of Kamala Harris's 2024 performance in those same districts [18]. In every district, Democrats achieved higher turnout relative to their registered voter base than they had in the 2024 general election—a reversal of the usual pattern in which Republican voters have shown superior off-cycle turnout in Florida [18].

The Tampa Race: A Second Potential Flip

HD-87 was not the only competitive Florida race on March 24. In Senate District 14, covering parts of Tampa, Democrat Brian Nathan—a Navy veteran and union leader—held a razor-thin lead over Republican Josie Tomkow as of election night [19]. The margin was narrow enough to trigger recount procedures, and a final result had not been declared as of March 25 [19].

If Nathan prevails, Democrats will have flipped two Florida legislative seats in a single night—one in deep-red Palm Beach County and one in the swing Tampa Bay region. Republican Hilary Holley held a Central Florida House seat in the third race on the ballot [3].

What It Means—and What It Doesn't

The Republican National Committee pushed back on the significance of Gregory's win. "A low-turnout state House special election is a snapshot of local quirks, candidate dynamics, and turnout math—not some grand verdict," an RNC spokesperson said [4].

There is merit to this caution. Special elections do feature lower and less representative turnout. The 28.82% participation rate in HD-87 was less than half of what a general election typically draws. Maples was a flawed candidate with a residency controversy and relatively weak direct fundraising. The seat's previous holder, Caruso, had deep community roots that Maples lacked.

The MCI Maps analysis of Florida's 2025 special elections acknowledged the same limitation: "It of course goes without saying that special election results cannot predict what will happen in a regular turnout general election" [18]. The analyst noted, however, that the consistency of Democratic overperformance across very different districts—rural and urban, North Florida and South Florida, congressional and state legislative—made the pattern harder to dismiss as a collection of one-offs.

Democratic strategists argue their candidates are winning not on an exclusively anti-Trump message but on economic issues. "They are not running on a sole anti-Trump agenda," the president of the Democratic Legislative Campaign Committee said. Instead, candidates "are looking for a path forward" on affordability and local concerns [5].

The historical parallel that haunts Republicans is 2017-2018. That cycle also featured consistent Democratic overperformance in special elections, followed by a midterm wave. Trump's current approval ratings, described in multiple reports as sitting in the 30s to 40s range [3], are comparable to or lower than his first-term numbers at a similar point.

The Structural Question for 2026

If the HD-87 result and the broader special election pattern represent something replicable in a general election environment, the implications for Florida—long considered a state trending Republican—are significant.

HD-87 had a Republican registration advantage, with Trump winning the district by 11 points in 2024. Numerous other Florida state House and state Senate districts share similar or narrower Republican margins. The Democratic Legislative Campaign Committee has publicly identified target districts for the 2026 cycle [20].

But replicability is the key question. General elections bring higher turnout, which in Florida has historically favored Republicans. Trump will not be on the 2026 ballot, which could depress GOP turnout—but could also remove the motivation that drove some anti-Trump voters to the polls in the special elections. The party registration landscape in Florida still shows a 1.48-million-voter Republican statewide advantage [9].

What is clear is that Democrats have found a formula that works in low-turnout environments: grassroots fundraising, a focus on affordability and insurance costs, and candidates who can credibly claim to be rooted in their communities. Whether that formula scales to a full election cycle remains the open question heading into November.