Democrats Flip Trump’s Mar-a-Lago District in Stunning Florida Special Election Win
The 2026 midterm elections gained a defining moment this week. Democrat Emily Gregory defeated Trump-endorsed Republican Jon Maples in a Florida special election to claim House District 87 — the Palm Beach district that includes President Donald Trump’s Mar-a-Lago estate. Gregory won by 2.4 percentage points, shocking political observers and sending a clear signal about Democratic momentum heading into November.
The previous Republican representative, Mike Caruso, won this same seat by 19 percentage points in 2024. Trump himself carried the district by 11 points that same year. Gregory’s victory marks the first time a Democrat has won the district this century — and for Democrats, the implications reach far beyond one state legislative seat.
A First-Time Candidate Beats the President’s Pick
Gregory, 40, is a small business owner and public health professional who had never sought elected office before this race. She focused her campaign squarely on affordability — rising housing costs, spiking gas prices, and soaring insurance premiums — rather than national politics. The approach resonated deeply with voters in a district home to one of the most prominent addresses in American politics.
Trump endorsed Maples the day before the election, posting on social media that the candidate had his “complete and total endorsement.” He also appeared at a Florida event days earlier, calling Maples on stage. None of it proved sufficient. Gregory won 51.2% of the vote to Maples’ 48.8% — a margin of just 797 votes.
“Not a lot of people thought this was possible. We believed our community deserved a leader willing to go to Tallahassee and fight for them with no other agenda than to lower costs.”
— Emily Gregory, the morning after her winMail-In Voting Contradiction Draws National Attention
The Florida result carried an additional subplot that quickly dominated national coverage. Palm Beach County voter records confirmed that President Trump cast a mail-in ballot in the special election — the same vote in which he endorsed Maples. The irony was sharp. Trump has repeatedly called mail-in voting a form of “cheating” and has pressed Congress to pass the SAVE America Act, legislation that would significantly restrict absentee voting nationwide.
One Republican voter at the polls, told by a CNN reporter that Trump had voted by mail, responded: “Are you kidding me? I had no idea.” The revelation highlighted the tension between the president’s public rhetoric on voting methods and his own electoral behavior — a tension that Democrats quickly amplified.
Gregory addressed her most famous constituent with measured diplomacy: “I will work as hard for every single one of the constituents in District 87 and not elevate anyone over the rest.”
The 29th Flip: What It Means for the 2026 Midterms
Gregory’s win is part of a broader pattern. Since Trump returned to the White House in January 2025, Democrats have flipped 29 seats in state legislatures across the country — from Republican control in Arkansas, New Hampshire, Texas, Georgia, and now Florida, in Trump’s own backyard.
“Mar-a-Lago just flipped red to blue. A Trump-plus-11 district in his own backyard shouldn’t be in play for Democrats, but tonight proves Republicans are vulnerable everywhere.”
— Heather Williams, DLCC PresidentDemocrats also recorded strong results in the November 2025 off-cycle elections, flipping more than 20 state legislative seats and winning gubernatorial races in Virginia and New Jersey by wider-than-expected margins. Affordability — not partisan identity — has been the consistent theme across these Democratic wins.
In November, all 435 U.S. House seats and 35 Senate seats are on the ballot. Democrats need a net gain of just three House seats to retake the majority. Republicans can afford to lose no more than two. The Florida result did not change the math — but it changed the mood.
Looking Ahead to November
The special election in Palm Beach County is one data point. But it is a loud one. Candidates in both parties are watching closely. For Republicans, the result raises a difficult question: Can Trump’s endorsement reliably move votes in districts where affordability, not ideology, drives turnout?
For Democrats, Gregory’s win is a test case. She did not run against Trump — she ran on local costs, local issues, and local accountability. If that formula travels from Palm Beach to suburban Ohio to competitive districts in Georgia and Michigan, the 2026 midterm elections could produce a significant shift in Congress.
AccuPay Systems will continue to track the election landscape and bring you the most important developments each week.
Additional Stories This Week
Senate Debates SAVE America Act as States Pass Their Own Proof-of-Citizenship Voting Laws
The U.S. Senate began floor debate on March 17 on the SAVE America Act — sweeping legislation that would require documentary proof of citizenship to register to vote in federal elections. The House passed the bill on February 11 by a narrow 218-to-213 vote. In the Senate, Republicans do not have the 60 votes needed to overcome a Democratic filibuster.
While debate stalls in Washington, Republican-led states are moving ahead independently. Florida passed its own proof-of-citizenship voter registration law this month, and Governor Ron DeSantis is expected to sign it. Critics argue the requirements could disenfranchise an estimated 9% of eligible voters who lack ready access to documents such as passports or certified birth certificates.
Read the full NPR report on state SAVE Act replicasWisconsin Governor Calls Special Session to Ban Partisan Gerrymandering
Wisconsin Governor Tony Evers signed an executive order calling the state legislature into a special session on April 14 to vote on a constitutional amendment that would permanently ban partisan gerrymandering. The move comes as a national redistricting battle intensifies — President Trump has pressured Republican-led states to redraw congressional maps mid-decade, while Democratic-led states are responding in kind.
Evers, who is retiring at the end of 2026, wants to lock in Wisconsin’s current fair maps before the next redistricting cycle in 2031. For the amendment to reach voters, it must pass two consecutive legislative sessions. Republican Assembly Speaker Robin Vos expressed cautious support for the concept but raised concerns about the proposal’s lack of procedural detail. The special session on April 14 will be a key test.
Read the full NPR report on Wisconsin’s gerrymandering push