In one of the most symbolically charged political upsets of 2026, Democrat Emily Gregory has captured a Florida state House seat in the very district that includes President Donald Trump’s Mar-a-Lago estate. It’s the kind of result that stops political operatives in their tracks — a first-time candidate, a small business owner, defeating a Trump-endorsed Republican in what was supposed to be safe GOP territory.
The race for Florida’s House District 87 was never meant to be competitive. The previous Republican occupant, Mike Caruso, had won his seat in 2024 by nearly 20 percentage points. Trump himself gave his opponent Jon Maples his “Complete and Total Endorsement” and personally urged supporters to turn out. And yet, when the votes were counted on March 24, 2026, Gregory led by 2.4 percentage points — 797 votes — with nearly all ballots tallied.
The message from Palm Beach County was impossible to ignore: even in Trump’s literal home district, voters are shifting.
Who Is Emily Gregory? The Underdog Who Flipped Mar-a-Lago
Emily Gregory is not a career politician. The 40-year-old grew up north of Palm Beach in Stuart, Florida, and built her career as the owner of a fitness company that serves pregnant and postpartum women. She is also a military spouse. This was her first run for elected office.
When she launched her campaign, few gave her a serious shot. The district had deep-red roots, and Trump’s personal involvement amplified the stakes considerably.
“When we started this, nobody thought it was possible. They thought we were crazy,” Gregory told her supporters on election night. “I knew my community. I knew we deserved better. We deserve a leader who will fight for us.”
Her win surprised even herself. Speaking after the result, she described feeling “pretty shocked” and having “a fairly out-of-body experience.” That candor resonated with voters who were tired of polished political messaging and eager for a voice that felt genuine.
The Mar-a-Lago District: What Made This Race So Significant
Florida’s House District 87 covers parts of Palm Beach County — the same stretch of coastline that houses Trump’s famous Mar-a-Lago club, which he has called his official residence since 2019. The president votes there by mail, keeps it as a base for weekend retreats, and has turned it into an informal hub for political allies and foreign dignitaries.
Winning here carries weight that goes far beyond the local legislative map.
Trump carried this Florida legislative district by about 11 percentage points in 2024, making Gregory’s victory a genuine swing — not just a narrow loss on favorable ground.
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.
The seat had sat vacant since August of last year, after Caruso stepped down to become Palm Beach County’s clerk and comptroller — creating the opening Gregory seized.
How Gregory Won: The Issues That Drove Voters to Flip
Affordability Was the Deciding Issue
Gregory and her Republican opponent Jon Maples both leaned heavily into economic concerns during the campaign. But the economic environment gave Democrats a clear advantage.
Democrats registered electoral gains in the November 2025 gubernatorial and mayoral elections, with the cost of living cited as a major issue on people’s minds. The US decision to join Israel in attacking Iran has driven up oil and gas prices, putting further inflationary pressures on Americans.
“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 Heather Williams, president of the Democratic Legislative Campaign Committee.
In Palm Beach County, where wealthy residents coexist alongside working families struggling with housing costs and grocery bills, that message landed hard.
Trump’s Approval Rating Was a Factor
Trump’s approval rating sits in the high 30s to the low 40s in most public polling, which has influenced elections throughout the U.S. over the past year.
Low approval numbers tend to energize the opposition. In a special election with characteristically low turnout, enthusiastic anti-Trump voters can punch well above their weight — and that appears to be precisely what happened in District 87.
Special Election Dynamics Favored Democrats
Special elections often feature low turnout, placing an especially high emphasis on voter enthusiasm that can swing results more effectively than in larger elections.
Democrats showed up. Republicans, perhaps lulled by the district’s deep-red history, did not turn out in the numbers needed to hold the seat.
The Bigger Picture: 29 Flips and Counting
Gregory’s win is not an isolated incident. It is part of a sweeping national pattern that has been building since Trump returned to the White House in January 2025.
Since Trump returned to the White House in January 2025, 29 seats in state legislatures around the country have been flipped from Republican control by Democratic candidates. Republicans, by contrast, have not flipped a single Democratic state legislative seat during the same period.
Here is a snapshot of notable Democratic flips in 2025 and 2026:
- Texas: Democrat Taylor Rehmet flipped a state Senate district Trump had won by 17 points in 2024.
- Arkansas: Democrats flipped a previously safe Republican seat earlier in 2026.
- New Hampshire: Another GOP-held seat fell to Democrats in a special election.
- Miami: In December 2025, Eileen Higgins became the first Democrat to lead Miami as mayor in nearly three decades, defeating a Trump-endorsed Republican.
- Florida HD-87: Emily Gregory’s win — in Trump’s own home district.
The pattern is consistent: Democrats are performing well above expectations in Republican territory, driven by economic anxiety, opposition to Trump’s policies, and high voter enthusiasm on the left.
Republican Reaction: Downplaying the Damage
The Republican National Committee moved quickly to frame the loss as a statistical anomaly rather than a warning sign.
“A low-turnout state House special election is a snapshot of local quirks, candidate dynamics, and turnout math — not some grand verdict,” said RNC Senior Adviser Danielle Alvarez.
There is a grain of truth to that. Special elections are not general elections. Candidate quality, local conditions, and turnout mechanics can all create results that don’t hold in November. Republicans held onto two other Florida special election seats on the same night Gregory won.
But 29 consecutive flips — zero in return — is hard to explain away as coincidence.
Democratic Reaction: Eyes on November
Democratic leaders were unrestrained in their celebration and immediately tied the win to the upcoming 2026 midterm elections.
“Donald Trump’s own neighbors just sent a crystal clear message: They are furious and ready for change,” said Democratic National Committee Chair Ken Martin.
“Mar-a-Lago just flipped red to blue, which should have Republicans sweating the midterms,” said Heather Williams, president of the Democratic Legislative Campaign Committee.
“If Mar-a-Lago is vulnerable, imagine what’s possible this November,” Williams added. “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.”
Florida Democratic Party chair Nikki Fried put it simply: “Democrats can run and win anywhere — including Donald Trump’s backyard.”
What This Means for the 2026 Midterm Elections
The midterm elections in November 2026 are shaping up to be a pivotal test for both parties. Here is what the Mar-a-Lago district flip signals for the road ahead:
1. Suburban and coastal districts are increasingly competitive. Districts once written off as safely Republican — particularly in high cost-of-living areas — are responding to economic frustration. Palm Beach County is a prime example.
2. Trump’s endorsement is not a guaranteed advantage. The president’s personal involvement in the District 87 race did not deliver a win. His endorsement may continue to mobilize his base in deep-red territory, but in competitive or swing-leaning districts, it can also energize opposition turnout.
3. Affordability is the dominant voter concern. Whether it is housing, gas prices, grocery costs, or inflation, the economic pain is real for ordinary families. Candidates who speak directly to those concerns — regardless of party — are connecting with voters.
4. First-time candidates can win. Emily Gregory had never run for office before. Her story as a small business owner and military spouse gave her authenticity that resonated in a community tired of career politicians.
5. Enthusiasm matters more than registration. Democrats are turning out in special elections at rates that outpace their registration share. If that enthusiasm holds into November, it spells trouble for Republicans defending seats in competitive districts across the country.
Key Takeaways: What Voters and Political Watchers Should Know
- Emily Gregory, a first-time candidate, flipped Florida’s House District 87 — which includes Trump’s Mar-a-Lago — defeating Trump-endorsed Republican Jon Maples.
- Gregory won by 2.4 percentage points in a district Trump carried by roughly 11 points in 2024.
- The win is part of a national trend: Democrats have flipped 29 Republican state legislative seats since Trump took office, with zero flips going the other way.
- Affordability — housing, gas, groceries — was the central issue driving voters.
- Democrats are treating the result as a bellwether for the 2026 midterms, with 650 state legislative seats in their sights.
Conclusion: Mar-a-Lago Flipped — What Comes Next?
The Democrat who captured Florida’s House seat in Trump’s Mar-a-Lago district did more than win a local legislative race. She sent a signal — from the president’s own neighborhood — that the political ground is shifting beneath the Republican Party’s feet.
Emily Gregory’s victory is not just a feel-good story about an underdog candidate. It is data. It fits a pattern. It reflects a national mood shaped by economic anxiety, falling presidential approval, and a Democratic base that is energized and organized.
The 2026 midterms are still months away, and a great deal can change. But if Democrats can win in Trump’s literal backyard, the political map for November has to be redrawn.
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