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PoliticsElections

Meet the 40-year-old Democrat who owns a fitness company for pregnant and postpartum women and just won in Trump’s district

By
Bill Barrow
Bill Barrow
,
Mike Schneider
Mike Schneider
, and
The Associated Press
The Associated Press
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By
Bill Barrow
Bill Barrow
,
Mike Schneider
Mike Schneider
, and
The Associated Press
The Associated Press
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March 25, 2026, 4:15 PM ET
emily
In this screenshot taken from video Florida State Rep.-elect Emily Gregory speaks with the Associated Press from Palm Beach, Florida, about her special election win where she flipped a district that is home to President Donald Trump's estate, Mar-a-Lago, March 25, 2026. AP Photo
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After a surprise victory in a Florida special election, Emily Gregory said she’s excited to represent all of her constituents — and that includes President Donald Trump.

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“I would love to have a conversation,” the Democrat told The Associated Press on Wednesday. “He’s welcome to call me, as I am his new state representative.”

The president’s Mar-a-Lago resort is part of Gregory’s district, which is anchored by Palm Beach. Although state legislative races rarely get the national spotlight, Democrats across the country were positively euphoric at the irony of their Republican nemesis being represented by one of their own.

Gregory’s victory is the latest example of how Democrats have flipped seats in a series of special elections that could be a sign of momentum in a midterm election year that will provide a political verdict on Trump’s second term.

Here was a 40-year-old first-time candidate who owns a local fitness company for pregnant and postpartum women defeating a Republican whom Trump had endorsed by saying he was backed “by so many of my Palm Beach County friends.”

Gregory’s win was especially sweet for Florida Democrats, who have been beaten down by years of Republican domination in what was once the consummate battleground state. Democrats are also hopeful that Brian Nathan will win a state senate seat in the Tampa area; the AP has not yet called that race but he currently has a narrow lead that is within the state’s automatic recount range.

“The pendulum swings in both directions,” Florida Democratic Chairwoman Nikki Fried told reporters. “Last night it swung hard in the state of Florida.”

She added, “If we can win in Donald Trump’s backyard, we can win anywhere.”

Florida Republican Chairman Evan Power did not return a message seeking comment.

Gregory said she’s ‘embedded in my community’

For Gregory, it has been a stunning introduction to the national spotlight.

“I believed in myself the whole time,” Gregory said, describing her political “naiveté” about the district and its conservative leanings as an asset. She was elected to finish the term of Mike Caruso, a Republican who resigned to become Palm Beach County’s clerk, and she would need to run again in November if she wants to keep the seat.

Gregory told the AP she did not make her contest about the president specifically, focusing instead on constituents’ concerns involving the economy and everyday costs — from fast-rising insurance in the hurricane-prone district to groceries and gas.

She described herself as a lifelong “proud Florida Democrat” but said she did not view herself as a Trump opposition leader. She said she will go to Tallahassee focused on proposals to limit insurance rate hikes, expand health care access, support public education and lift “huge, crushing burdens on the average Florida family.”

“I just see myself as very embedded in my community, very representative of District 87,” she said. “And I’m so humbled and proud to be their representative.”

Trump endorsed Gregory’s opponent, Jon Maples, and cast a mail ballot in the contest. The president reiterated his support for Maples on the eve of the election with a social media post addressed to “ALL GREAT PATRIOTS.”

As of midday Wednesday, Trump had not mentioned the outcome of the race.

Gregory expects to be sworn in before a special legislative session that begins April 20 to redraw the state’s congressional map. It’s a Republican initiative intended to boost the party’s chances to hold onto its thin majority in the U.S. House, and Gregory said she plans to oppose the effort.

She described the session as a “complete power grab” resulting from “the president’s call to gerrymander in favor of Republicans.”

Florida Dem chair says candidates matter

Fried praised Gregory and Nathan, a 45-year-old veteran and union worker, as quality candidates who could capitalize on the broader political environment.

“The type of person and connection on the issues matters,” Fried said.

Gregory flipped a seat that her Republican predecessor had won by 19 percentage points. Fried said Trump carried the district by 11 points in 2024.

Republicans still dominate the Florida Legislature, and they have been considered heavy favorites to hold the governor’s office in November, four years after Gov. Ron DeSantis won a blowout reelection campaign.

But Fried and other Democrats insisted the trends suggest a competitive landscape. She noted that Tuesday’s victories followed two congressional special elections in 2025 when Florida Democrats lost but dramatically narrowed the usual margins in heavily Republican districts.

“You’ve seen tremendous overspending by Republicans,” Fried said of the current cycle. “It’s not working.”

Democratic gubernatorial candidate David Jolly said Wednesday the results demonstrate an upswing for the party as long as candidates address the economy.

“Change is here,” said Jolly, a former Republican congressman who switched parties. “Voters are giving us an opportunity in Florida that they haven’t given us in years.”

A spokesman for Republican U.S. Rep. Byron Donalds, whom Trump has endorsed for Florida governor, took at least some notice of the latest results.

“We constantly assess how we execute our strategy — that’s just good campaigns,” said Ryan Smith, Donalds’ chief campaign strategist. “What won’t change is our mission: President Trump endorsed Byron Donalds to deliver real results and defend the Florida Dream, and that’s what voters can expect to see from us.”

Gregory, meanwhile, said she’s ready to get to work, including for Trump.

“I will work as hard for every single one of 180,000 constituents in District 87,” she said, “and not elevate anyone over the rest.”

___

Barrow reported from Atlanta.

Subscribe to Fortune Gulf Brief. Every Tuesday, this new newsletter delivers clear-eyed, authoritative intelligence on the deals, decisions, policies, and power shifts shaping one of the world’s most consequential regions, written for the people who need to act on it. Sign up here.
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