Democrat Emily Gregory knew her upset victory on Tuesday night in Florida was a big deal when her third-grader told her, “Mom, you really surprised me.”
Gregory, a first-time candidate and fitness business owner, defeated Jon Maples, a Republican endorsed by President Donald Trump and aligned with his policies. The two were going head-to-head in a Florida special election for a district that includes the president’s Palm Beach home, Mar-a-Lago. The Democrat’s win was an upset: Despite Palm Beach County leaning left, this district was a red enclave, with Republicans holding a significant voter-registration advantage and the Republican who vacated the seat last year winning it by 19 percentage points in 2024.
The Democratic win is part of a broader trend of the party overperforming in elections since Trump assumed his second term. In several races, from gubernatorial contests in Virginia and New Jersey to downballot races in such red states as Texas and Arkansas, Democrats have either won Republican-held seats or outperformed their previous numbers. In Florida, Gregory’s victory — along with that of Democrat Brian Nathan, who also narrowly pulled off an upset in a Tampa-area state Senate special election — has given the out-of-power party a needed boost and raised hopes that the 2026 midterms could bring significant Democratic wins nationwide.
“This is one in a trend that we have seen across the country,” said Rep. Suzan DelBene (Washington), chair of the Democratic Congressional Campaign Committee. “If you talk to folks on the ground across the country and you see what’s happened in special elections, it has been a consistent trend. … Republicans know they are losing.”
Democrats were not shy about their excitement. Reps. Lois Frankel and Kathy Castor — who represent the congressional districts that flipped in Palm Beach and Tampa, respectively — kicked off House Democrats’ weekly caucus meeting Wednesday morning by celebrating the wins. Minority Leader Hakeem Jeffries (New York) reminded colleagues that Democrats have flipped 30 legislative seats across the country since Trump took office last year.
While some Republicans have argued that small special election results are being overblown, others privately acknowledge that the signals are troubling for their party.
“Floridians want lower costs. They want their leaders focused on making Florida more affordable, solving real problems, not political distractions,” Gregory said. “That’s what the people really want their leaders focused on.”
So what trends are Democrats happy about?
Since the start of 2025, Democrats have used special elections to flip a dozen state legislative seats, while Republicans have not flipped one. When off-year elections in 2025 are included — in which Democrats dominated both statewide and downballot contests in Virginia and New Jersey — the number of flipped seats rises to 30.
This, coupled with Trump’s slumping approval ratings, has Democrats hopeful that November’s elections could be a chance to sweep Republicans out of power in the House and alter control of many state legislatures.
“If we put in the work like we did in these Florida races, the data tells us 650 flips could be in play this November — the largest gain for Democrats in over two decades,” said Heather Williams, head of the Democratic Legislative Campaign Committee, the group tasked with helping downballot Democrats. “2026 is our opportunity to transform the trajectory of the country for years to come.”
In some cases, the overperformance is purely symbolic. Republicans have continued to win in deep-red districts, but Democrats have kept the races closer than expected. In Florida, despite Gregory’s and Nathan’s wins, Republicans continue to hold a supermajority in the state House and Senate.
Why does winning Trump’s district matter?
Gregory’s win is dripping with symbolism: Trump’s neighbors rejected his brand of politics in a special election, and the president will be represented by a Democrat in the Florida House.
But this district and Florida in general represent the kind of places where Democrats have lost ground in the past decade. And Democrats acknowledge it is in places like this district where they will have to improve their standing with voters to have a shot at surprise wins in November.
“In Florida and nationwide, you don’t have to be a Democrat to vote for a Democrat. That is what we are seeing,” said David Jolly, the former Republican congressman who is running for governor in Florida as a Democrat. “Last night is consistent with a massive trend towards change here. Voters are telling us what they want. Voters are telling us that they need more attention paid to the economy, to health care.”
Given that Republicans enjoyed a double-digit voter-registration advantage in the district, Gregory was upbeat that registered Republicans turned out in a race in which the Democrat ultimately won, suggesting that some Republicans voted for the Democratic candidate.
“A lot of independents and Republicans must have voted for me, just looking at the returns,” Gregory said.
What does Gregory say about what her win means?
Gregory, who plans to run for reelection in November to keep her seat, is well aware of the national conversation about her contest.
“I went through the full spectrum of human emotions yesterday afternoon,” she said. “I was just thrilled because my theory of the case the whole time was my neighbors, my community … want a fairer, kinder Florida that truly works for all of us. And that is what has been my guiding light the whole time.”
The Democrat knew her race was a long shot. She told The Washington Post a few days before Election Day that while she viewed the seat as flippable, she understood she was the underdog.
Asked Wednesday about Republicans who are suggesting that her win is just a one-off, Gregory said, “Well, I think if I were in their shoes, that’s what I would also say.”
Are Republicans concerned?
Republicans, mostly, don’t want to talk about the Gregory win.
Trump, ever quick to take to social media, has not mentioned the Republican loss in his home district, despite having endorsed Maples and privately appearing alongside him at Mar-a-Lago before Election Day.
Maples has yet to concede to Gregory. Neither he nor the White House responded to a request for comment.
“The White House political shop knows how important turnout will be in the midterms, and that’s why they’ve gone so far as to hold a midterm convention to stress the importance of voter turnout,” said Chris Pack, a longtime Republican operative. “Anyone who says you can extrapolate general election turnout for U.S. House and Senate races based on a handful of local elections has no idea what they’re talking about.”
Why do Democrats do better in special elections?
Democrats have become the party that does better in low-turnout elections, a dramatic paradigm shift in political thinking, given that Republicans were seen not too long ago as the party that needed lower turnout to succeed.
Voter participation in special elections is always relatively low. The contests often happen at times not associated with voting, and spending on ads, campaign infrastructure and get-out-the-vote efforts pales in comparison with spending around a general election.
Turnout in the special election won by Gregory is expected to come in around 30 percent — dramatically lower than what the turnout will be when the seat is back on the ballot in November, when turnout will spike because of other competitive races.
Trump has been a significant driver of this change. Ever since he took to the political scene in 2015, he has turned out low-propensity voters at a dramatic rate, boosting nationwide turnout and creating a scenario in which his party does better when those unlikely voters head to the polls and turnout is high.
When Trump won in 2024, the U.S. Census found that 65.3 percent of eligible voters cast ballots, just slightly lower than the record-breaking 66.8 percent in 2020.
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