March 24, 2026 — Palm Beach, Florida — In one of the most symbolically charged election results of Donald Trump's second term, Democrat Emily Gregory won the special election for Florida House District 87 on Tuesday night — a Palm Beach County district that includes Mar-a-Lago, the president's private club and legal residence. Gregory, a 40-year-old Army spouse and fitness center owner running for office for the first time, defeated Jon Maples — a Republican candidate who carried Trump's "Complete and Total Endorsement" — by 766 votes, flipping a seat Trump won by 11 percentage points just 16 months ago. It is Democrats' 30th state legislative flip since Trump returned to the White House in January 2025. Republicans have flipped zero.
📊 The Final Numbers: Closer Than Expected, But a Flip Is a Flip
The final results confirmed what the Associated Press, CNN's Decision Desk, and NBC News all projected Tuesday night:
| Candidate | Party | Votes | Percentage |
|---|---|---|---|
| ✅ Emily Gregory | Democrat | 17,047 | 51.15% |
| ❌ Jon Maples | Republican | 16,281 | 48.85% |
| Total votes cast | 33,328 | — | |
Gregory's winning margin of 766 votes — just 1.3 percentage points — reflected the difficulty of the terrain. Trump won this same district by approximately 11 points in 2024. The previous Republican incumbent, Rep. Mike Caruso, had won re-election here by 19 percentage points in 2024. The seat had been vacant since August 2025 when Caruso left to become the Palm Beach County clerk and comptroller.
The swing — from Republican +19 to Democrat +1.3 — represents an approximately 20-point shift toward Democrats in a single cycle.
🗣️ Emily Gregory: 'Nobody Thought It Was Possible'
Speaking to supporters at her election night party, Gregory was visibly emotional. "When we started this, nobody thought it was possible. They thought we were crazy," she said.
Gregory, a 40-year-old Army spouse who owns and runs a Jupiter-based fitness center for pregnant and postpartum women, ran as a first-time candidate focused entirely on kitchen-table issues. In an interview with CNN's Erin Burnett just after polls closed, Gregory said Trump was not a factor when it came to her campaign.
"Everyone is feeling that affordability crisis and the last thing that Florida families needed when they're struggling is $4 gas," Gregory said — a direct reference to the Iran war-driven gas price surge that has pushed the national average to $3.84 per gallon.
In a statement to the Washington Post, Gregory said: "Tonight's result sends a clear message that people want Florida to move in a new direction, one where leaders focus on lowering costs and standing up for working families."
🐴 Democrats Erupt: 'We Can Win Anywhere'
Democratic officials were barely able to contain their enthusiasm — particularly given the symbolic power of winning in the president's literal home district.
DNC Chair Ken Martin posted on X: "Donald Trump's own neighbors just sent a crystal clear message: They are furious and ready for change. While Trump is partying with his billionaire donors and building gilded ballrooms, Americans are being left behind and raising hell with their votes. If Democrats can win in Trump's own backyard, we can win anywhere. From now until November, Democrats are all gas and no brakes."
DLCC President Heather Williams was even more direct: "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."
Florida Democratic Party Chair Nikki Fried said: "Democrats can run and win anywhere — including Donald Trump's backyard. This victory reiterates an undeniable trend in Florida: with year-round organizing and infrastructure investment, Democrats can run and win anywhere."
🐘 Republican Spin: 'Low Turnout, Local Quirks'
The Republican National Committee moved quickly to downplay the result. RNC Senior Adviser Danielle Alvarez said in a statement: "A low-turnout state House special election is a snapshot of local quirks, candidate dynamics, and turnout math — not some grand verdict."
The RNC's argument — that special elections are unreliable predictors of general election performance — has some historical merit. Special elections often feature unusually low turnout, which can favor whichever party has more motivated voters at that particular moment.
However, the scale of the shift — and the pattern across 30 consecutive Democratic flips without a single Republican flip — is difficult to explain away with "local quirks."
✉️ The Trump Mail Ballot Irony
In a detail that immediately went viral, Trump voted by mail in Tuesday's special election — even as he continues to publicly denounce mail-in voting as fraudulent and pushes Congress to pass the Save America Act, which would sharply restrict the practice nationwide.
Palm Beach County voter records confirmed that Trump voted by mail and that his ballot was counted. A White House spokesperson said Trump's voter ID bill "has commonsense exceptions for Americans to use mail-in ballots for illness, disability, military, or travel" — and noted that Trump "is a resident of Palm Beach and participates in Florida elections."
One Palm Beach County voter, Hall, told CNN she was stunned: "Are you kidding me? I had no idea. If he's against something, why are you doing it?"
📈 The Bigger Picture: 30 Flips, 0 Republican Gains
Tuesday's result in Florida HD-87 is the latest data point in what has become one of the most consistent political trends of Trump's second term. Since Trump returned to the White House in January 2025:
- 🔵 Democrats have flipped 30 Republican state legislative seats
- 🔴 Republicans have flipped ZERO Democratic seats
- 📍 Flips have occurred in: Arkansas, New Hampshire, Texas (Trump +17 district), and now Florida (Trump +11 district)
- 📊 Trump approval rating: High 30s to low 40s in most public polling
- 🇮🇷 Iran war factor: Americans have largely taken a dim view of the war in public polling
Florida's 87th District is the 10th GOP-held state legislative seat Democrats have flipped around the country since Trump took office again last year. Mar-a-Lago will now be represented by a trio of Democrats across the Florida state House, Senate and US House — though Republicans maintain overall control of all three.
💡 Why Gregory Won: The Affordability Message
Political analysts point to three factors that drove Gregory's upset win:
1. The Affordability Crisis
Gregory focused relentlessly on cost-of-living issues — gas prices, grocery prices, property insurance, and housing costs. In a district where Trump's brand was supposed to be unassailable, the Iran war-driven gas price surge gave Democrats a concrete economic argument that cut through partisan loyalty.
2. No-Party Affiliated Voters Broke for Democrats
The race ultimately came down to turnout among no-party affiliated voters — who make up roughly a quarter of Florida's electorate and have shown signs of leaning Democratic in recent elections. Gregory won this group decisively, according to analysts.
3. Voter Enthusiasm Gap
Special elections place an especially high premium on voter enthusiasm. Democrats showed up. Republicans, despite Trump's personal endorsement post on Monday night, did not turn out in sufficient numbers to overcome Democratic energy.
📅 What It Means for November 2026
Democrats are heading into the 2026 midterm elections with a clear wind at their backs. A series of lopsided or improbable victories in special elections — including flipping a Texas district Trump won by 17 points, and now a Florida district Trump won by 11 points — suggests the political environment is significantly more favorable to Democrats than recent history in these states would suggest.
However, political strategists on both sides caution against over-reading special election results. The midterms in November will feature dramatically higher turnout — which historically benefits the party that has the larger base, not necessarily the party with more motivated voters at any given moment.
What is clear: the combination of the Iran war, gas prices, healthcare, and affordability has created a Democratic message that is working — even in places where it was not supposed to.
📊 Key Facts at a Glance
| Detail | Information |
|---|---|
| 🗳️ Race | Florida House District 87 Special Election |
| ✅ Winner | Emily Gregory (Democrat) |
| ❌ Loser | Jon Maples (Republican, Trump-endorsed) |
| 📊 Final margin | Gregory 51.15% — Maples 48.85% (766 votes) |
| 📍 District includes | Mar-a-Lago, Palm Beach, Jupiter |
| 📈 Trump's 2024 margin | +11 points |
| 📉 Previous R margin (2024) | +19 points (Caruso) |
| 🔄 Swing toward Dems | ~20 points |
| 🔵 Dem legislative flips (total) | 30 since Jan 2025 |
| 🔴 GOP legislative flips (total) | 0 |
| ✉️ Trump voted by | Mail ballot (despite opposing mail voting) |
| 👤 Gregory background | Army spouse, fitness center owner, first-time candidate |
Sources: CNN Decision Desk (March 24, 2026), Washington Post (March 24), NBC News (March 24), AP (March 24), Fox News (March 24), WFLX/Nexstar (March 24), WSLS/AP (March 24), Local10/WPLG (March 24), DNC official statement (March 24, 2026) — all data current as of 9:00 PM ET Tuesday March 24, 2026.
Last updated: March 25, 2026.
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