Democrat Emily Gregory’s stunning upset win on March 24 in the Florida House of Representatives district that includes President Donald Trump’s Mar-a-Lago home has made her a political bright light.
Her party and media outlets see her as a star, high-profile proof that Trump’s unpopularity will doom Republican Party prospects in state legislative and congressional races this fall. But Gregory’s recently defeated opponent, Jon Maples, is already at work in a bid to make Gregory a comet, a political flash whose light fades with a general election defeat in November.
For now, Gregory can still bask in the glow of that special election win on March 24, which will see her sworn into office — however briefly — next week and then join fellow legislators in Tallahassee.
The 40-year old mother of three, military spouse and small business owner was exuberant but unharried during a recent interview at her neat, elegant home in Jupiter. Her husband, U.S. Army Lt. Col. Andrew Gregory, was trying to corral the family’s spirited dogs for a walk that would give Emily Gregory a few quiet minutes to talk. Pictures of the couple’s three children and art hung on the wall.
The representative-elect was still processing the whirlwind loosed by her win over Maples, who ran with Trump’s endorsement in a Juno Beach-to-Manalapan coastal district Republican Mike Caruso won by 19 percentage points just two years ago.
Gregory shook her head and smiled when asked which television shows she’s been on since the election.
“I don’t want to leave anybody out,” she said. “There’s a spreadsheet somewhere. Alex Witt (of MS Now) I did the same day as Rev. (Al) Sharpton. I did Erin Burnett (of CNN) twice. I did Erin Burnett in the car on the way to my watch party before I knew for sure whether I’d won or not, which was crazy. And then I went on the next night. I did CNN yesterday morning. Did Bloomberg this weekend. And all of the locals.”
Limelight brighter than Emily Gregory expected
The appetite for the story of the political neophyte who beat a Trump-backed candidate in the president’s own state House district was insatiable.
“I anticipated about one one-hundredth of that,” Gregory said of media outlet interest. “I thought, like, maybe one. I thought articles, like local articles. I thought The Palm Beach Post would cover it. I tried to fundraise and generate excitement off this. I did not expect hundreds (of responses).”
Trump hasn’t been shy about attaching himself to any klieg light moment, as evidenced by his surprising White House welcome of newly-elected New York City Mayor Zohran Mamdani, whom he had earlier called a “100% Communist lunatic.”
Gregory, however, hasn’t gotten a moniker or a call from the president.
“I have said my number is probably not that hard to find, and I would welcome a call,” she said.
November election ahead for Gregory v. Maples, but other seats too
Maples, meanwhile, is waiting for a second shot at the District 87 seat. He has already filed to run in the November general election.
Given Republican pique at Maples’ defeat — and Democratic glee at Gregory’s surprise win — both candidates are expected to raise hundreds of thousands for the race, far more than is typical for a local legislative race.
Gregory said she just opened a new campaign account for the general election, as is required by law, and is hoping the attention of her victory will spur voters to stay engaged in her race.
“I do hope that, while people are thinking about this and they’re so excited, we can turn it into some material support,” she said.
Unlike Maples, Gregory will soon have to run for office while holding office. Gov. Ron DeSantis has called a special session in late April to take up congressional redistricting, and state legislators could also end up in Tallahassee earlier to finish the budget.
Gregory will have a vote in those battles.
For half a dozen years now, Democrats have had a vote in Tallahassee but not much of a voice. Republicans have super majorities in both the state House and the state Senate, giving them the power to introduce, amend and pass legislation with only the Democratic input they allow. And that hasn’t been much.
Gregory said she believes her win indicates that reality is about to change.
“I believe that, after November, we will no longer be in a super minority,” she said. “I am Democrat 34 (in the 120-member House), and I think we will pick up six or more seats in November. At the same time, I like our chances for the governor’s mansion. I think we’ll have a Democrat in the governor’s mansion, and I we’ll have 40 or 40-plus one, 40-plus something in the state House. I don’t know the seats in the state Senate that well. I think by the time the next legislative session happens, we can be a very different place. And that would be hugely beneficial to all Floridians.”
Gregory said she heard over and over on the campaign trail from voters who are tired of one-party rule in Tallahassee.
“When I talk to stakeholders, business, any advocacy group, they say, ‘We want the numbers to be closer. We want there to be mediation,'” she said. “Otherwise, with one-party rule, they don’t have to talk to the Democrats. They don’t have to negotiate, and they haven’t been for several years now.”
Gregory said she’s ready to work with all comers in Tallahassee.
“I’m a very pragmatic, work-across-the-aisle person in every aspect of my life — as a small business owner, on the school advisory council at my children’s school. I was the liaison for service members and their families in the Army to get them the support they needed. In all of those roles, I’m just looking for good ideas. I think partisanship and the toxicity that’s come with it has turned off a lot of people in the last 10, 20 years. If I can be a small part of changing that narrative, of saying we don’t have to operate this way, we can choose to operate a different way, then that’s part of my mission as I see it.”
Affordability in the time of $10k home insurance premiums
Priority No. 1, Gregory said, is affordability.
“The big thing I’ve been talking to with voters is just relief, relief from the cost of living, specifically with property insurance,” she said. “I think there’s real reform needed there. Some that help the insurance industry and some that hold them accountable. I support a state catastrophic fund in which the state self-insures against catastrophic loss and wind mitigation. We’re taking that hurricane giant risk off the back of private insurers. I’ve seen estimates that that would reduce our premiums 70%. Ours was like $3,000-ish and it’s like $10,000-ish now. That’s common. That’s, like, what I’m hearing. That just results in such a tightening of all of our household budgets. And then, of course, the first-time buyer has trouble entering the market, and then the senior has trouble staying in the market.”
Gregory talks with depth on issues like property insurance, public education and Medicaid expansion. For however long she gets to be in Tallahassee, she said she’s going to remember why she’s there and the family dynamics that make her service possible.
She credits her husband for taking up more of the kid and household tasks so she can get to work for constituents.
“We’ve been looking at service as a team sport, truthfully,” she said. “For the first 15 years of our relationship, his service and his career has been prioritized. And now, maybe this next 15 years — or at least, the next eight months — my service becomes the priority and then shifting the family.”
While Gregory did not display a zeal for sharp political attacks during the campaign, she did mix her fight for affordability with some shade directed at legislators for the recent renaming of Palm Beach International Airport in Trump’s honor.
“So just any way that I can bring costs down for District 87 families, that’s my only priority,” she said. “That’s the only reason I ran in the first place — to make all of our lives better. The leadership I saw in Tallahassee was not tackling any of these issues. They’re re-naming things.”
Wayne Washington is a journalist covering education and Riviera Beach development for The Palm Beach Post. You can reach him at wwashington@pbpost.com. Help support our work; subscribe today.
This article originally appeared on Palm Beach Post: Emily Gregory win in Trump district ignites frenzy she didn’t expect
Reporting by Wayne Washington, Palm Beach Post / Palm Beach Post
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