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By Sam Stevenson
Associate News Editor
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The Florida Democrat who flipped President Donald Trump’s backyard has told Newsweek her party cannot rely on momentum alone in the midterms, warning that "nothing replaces doing the work."
Fresh off flipping a long‑held Republican district that includes Trump’s sprawling 17-acre Mar-a-Lago Club, Emily Gregory says her colleagues must stop looking for shortcuts ahead of the midterms.
Why It Matters
Gregory’s upset win in a district long seen as safely Republican has been cited as evidence of Democratic momentum ahead of November.
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But she warns against reading recent results as a substitute for grassroots effort.
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What To Know
Gregory, who was officially sworn into office on Tuesday this week, did not set out to run a nationally symbolic campaign.
Her decision to seek office in Florida’s 87th District grew from daily pressures closer to home—rising costs, struggling public schools, and an insurance system she says is failing ordinary families.
"I really found the state legislature to be what is impacting my life day today the most," Gregory told Newsweek, speaking via video link.
With three children in public schools, she said policies passed in Tallahassee—from universal school vouchers to health care access—had more immediate consequences than anything happening in Washington.
Property insurance played a central role in her decision to run.
Gregory said her own premiums had jumped more than 300 percent, a strain she said mirrors what thousands of her neighbors are facing.
Health care access, particularly Florida’s refusal to expand Medicaid, was another recurring concern she heard while campaigning.
That focus on tangible, local issues—rather than national political fights—shaped how she ran her race.
Gregory said she refined her message not by following party dogma, but by speaking directly with voters across the district.
"I talked to thousands of District 87 voters," she said. "If there’s one message I want to underscore, it’s that nothing replaces doing the work. You have to knock every single door, make every call, and show up."
She cautioned Democrats against assuming that tools like social media or high‑profile endorsements can replace face‑to‑face campaigning.
Listening, she said, often changed her own thinking—including on questions like targeted property tax relief for first‑time homebuyers locked out of an increasingly expensive market.
‘Earn Every Single Vote’
Gregory’s victory came amid a series of recent Democratic wins in special elections, which party leaders have pointed to as signs of momentum heading toward the midterms.
But she rejected the idea that such outcomes signal an inevitable "blue wave."
"We can look at momentum, and we can say we’re on the right side of the issues," she said. "But if Democrats expect some blue wave to sweep them up and they don’t have to earn every single vote, that’s not the takeaway."
Instead, Gregory argued, recent elections show both sides something different: that special elections should not be dismissed, but also should not be treated as guarantees of future success.
Voters, she said, were far more interested in practical concerns—insurance costs, taxes, and public services—than in national political symbolism.
Endorsements from prominent figures did not appear to carry much weight at the door.
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Focus on Issues Voters Care About
On policy, Gregory said one of her top priorities is holding insurance companies accountable, including reining in steep year‑over‑year rate increases and scrutinizing profits while families struggle.
She supports exploring a state‑backed catastrophic insurance model that could remove hurricanes from private insurers’ risk pools—a change she said could dramatically stabilize premiums.
She also criticized proposals to abolish property taxes as a cost‑of‑living fix, calling them misleading and dangerous.
Eliminating property taxes, Gregory said, would simply shift the burden elsewhere—through higher, more regressive sales taxes or other revenue measures—while jeopardizing funding for essential services like schools, public safety, water systems, and sanitation.
"Across‑the‑board abolition is irresponsible," she said. "Our trash still has to be picked up. We still need municipal services."
While she supports Florida’s homestead exemption as sound policy, Gregory said long‑standing exemptions can create sticker shock for first‑time buyers when aging properties finally change hands.
That, she argued, is where focused relief should be considered—not in sweeping tax cuts that obscure tradeoffs.
Trust Matters More Than Branding
Underlying her approach is a broader belief that trust matters more than party branding, particularly as more voters register as independents.
Gregory said she did not expect everyone to agree with her on every issue, but promised transparency in how she reaches decisions.
"Not everyone will agree with me, but I will always explain my thought process," she said. "People may not love every outcome, but they understand how you got there."
She also warned candidates against campaigning on issues beyond the scope of the office they are seeking.
Foreign policy, Gregory noted, is not something a state legislator can meaningfully influence.
"There’s a lot you can do from Tallahassee," she said. "There’s also a lot that’s just outside the scope."
What Happens Next
Gregory said her immediate focus will be on securing resources for District 87 as Florida lawmakers return to Tallahassee to pass a delayed state budget.
She expects to advocate for infrastructure funding, including sewage and water projects in communities that went unrepresented during the last legislative session.
Property taxes are also likely to return to the agenda in upcoming special sessions, along with the possibility of renewed congressional redistricting efforts—fights she said she is prepared to take on.
Looking further ahead, Gregory said she hopes that after seeking reelection, she will be able to introduce legislation of her own during a full legislative session in 2027.
Despite her district’s growing national profile, she dismissed the idea that it has changed her priorities.
"My boss is the voters of District 87," Gregory said. "That’s who I get up in the morning to serve."
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