After upset HD 87 flip, Emily Gregory says Dems ‘have the momentum’ to win more in November

Emily Gregory believes her upset win in House District 87 last week can be a blueprint for other Democrats, who are now on a roll in the Sunshine State.

Speaking on CNN News Central, Gregory said her 2.3-percentage-point victory last Tuesday in the home district of Republican President Donald Trump — where no Democrat had previously won this century — shows Florida’s Midterm odds are increasingly in Democrats’ favor.

“I like our chances,” she said Monday when asked by anchor John Berman about her party’s chances in the Midterms.

“Maybe I’m a half-glass-full kind of gal, but I saw the pathway forward for me in this district eight, nine months ago when I filed. And I see a different pathway forward for Florida. And I think that Florida Democrats are on the right side of the issues and we have the momentum.”

Gregory made clear that for other Democrats to replicate her win in November, they’ve got to employ a comparably strong ground game, which in her case included personally knocking on “a few thousand doors” and enlisting the help of “200 volunteers.”

“It’s not as complicated as maybe the political punditry class thinks it is,” she said. “It was just talking to as many voters as I could. And I think that it started with just a small group. And it’s the definition of grassroots. It grew from there.”

Gregory defeated Republican Jon Maples, a former Lake Clarke Shores Council member, with 51.15% of the vote in a Palm Beach County district whose previous Representative, Republican Mike Caruso, last won re-election by 19 points.

Trump, who endorsed Maples in the race, carried the district by roughly 9 points in 2024.

She won despite having less than half the campaign funds Maples did and with far less help from her state party, whose resources have dwindled in recent cycles.

How? Strong messaging, according to Gregory, who said she eschewed engaging in noisy political rhetoric and instead focused on kitchen-table issues affecting most voters.

“I asked, you know, what are you struggling to, you know, make ends meet? Are you struggling to save for the future? Because I know we are, and my friends are,” she said. “So, we talked about property insurance. It has skyrocketed over the last five, six years. … At the same time, health care has just gotten more expensive and harder to maintain, (and) public education has really come under fire in the state, and we’re really gutting it.”

She said Democrats must be more specific and avoid a one-size-fits-all message, even if the overriding problem is universal.

“Affordability is an issue nationally, but you can’t just plug and play what the affordability issues are here in coastal Palm Beach County,” she continued. “I don’t know what the affordability issues are in Wisconsin or South Carolina. You will only know that by going and talking to as many voters as you possibly can and helping them inform, you know, your message and your policy solutions.”

As for whether she’s received a call from Trump — who has repeatedly expressed concerns about mail-in vote tampering despite voting by mail in the HD 87 race himself — Gregory said no, at least not yet.

“I would welcome the call,” she said. “And I’m sure my phone number is not that hard to get.”

Berman did not ask Gregory about the Saturday arrest of Democratic election volunteer John Panicci, whom authorities accuse of stealing voting equipment days before the March 24 Special Election in HD 87.

Notably, investigators said the encrypted access key Panicci allegedly took was solely for training databases, though some officials have suggested the key could be reverse engineered to access live voting systems.

The Republican Party of Florida said in an X statement Sunday that it expects a “full, thorough investigation” and that it “will be closely monitoring every development to ensure complete accountability.”

Gregory’s win, which came the same day as another upset by Brian Nathan in Senate District 14, added to other recent Democratic victories in Florida. Those include Andy Thomson’s win as Boca Raton Mayor this month and Eileen Higgins’ landslide triumph in December, when she became the first woman ever elected Mayor of Miami.

Thomson’s win marked the first time a Democrat won the Boca Raton mayoralty in at least 45 years. Higgins is the first registered Democrat to win the Miami Mayor’s race in nearly 30 years.

On Monday, the Democratic National Committee announced it is launching a first-ever Midterm year partisan voter registration effort in Florida, as well as a new playbook to guide operational best practices for candidates and staff.

Party officials say the effort is part of a broader strategy to rebuild Democratic infrastructure in Florida, where the number of registered Democratic voters since 2018 has fallen by 18.6%, while Republicans — who now hold a nearly 1.5 million-voter advantage statewide — increased their rolls by more than 17%.