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Four Things to Know About a Democrat’s Win in Trump’s Backyard

March 25, 2026
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Four Things to Know About a Democrat’s Win in Trump’s Backyard

In an upset filled with unmistakable symbolism, a 40-year-old Democratic mother and military spouse on Tuesday won a Republican-held Florida State House seat that includes President Trump’s Mar-a-Lago estate.

And in what would be another upset, a Democratic electrician is clinging to a 408-vote lead — or half a percentage point — in a bid to flip a State Senate seat in West Tampa.

Here’s what we know:

The political newcomers focused on Tallahassee.

Emily Gregory, the winner in Palm Beach County, highlighted her background in public health and as a small-business owner. Instead of focusing on the most famous constituent in her district, which runs along the Atlantic coast, Ms. Gregory, a 40-year-old mother of three who was a first-time candidate, said that the issues concerning her family and her neighbors — affordability, housing and health care — were being ignored in the state capital, Tallahassee.

Brian Nathan, the Democrat in West Tampa, is a Navy veteran and electrical workers union leader, part of a wave of working-class candidates running as Democrats this year. As wages stagnate and insurance rates soar, a major concern in Florida Mr. Nathan, 45, vowed to fight for working-class families because “too many legislators are distracted by divisive culture wars.”

A winning streak continues.

Republicans had been favored in House District 87 in Palm Beach County, which Mr. Trump carried by 11 percentage points in 2024. The previous state representative, Mike Caruso, had won by 19 percentage points. Gov. Ron DeSantis last year appointed Mr. Caruso as county clerk, which prompted Tuesday’s matchup between Ms. Gregory and Jon Maples, a financial planner. Mr. Trump endorsed Mr. Maples and hosted him at Mar-a-Lago.

But once again, Democrats overperformed. Since the 2024 election, Democrats have flipped more than two dozen seats in Republican-led or battleground states — including ones in Arkansas and New Hampshire this month, and Texas earlier this year. Republicans, meanwhile, have not captured any Democratic seats.

Heather Williams, the president of the Democratic Legislative Campaign Committee, said: “Even before the victories this week, the D.L.C.C. had Florida on our target map for the midterms. Our data shows us 650 statehouse seats are in play this year nationwide — including the opportunity to pick up seats and break both G.O.P. supermajorities in Florida.”

Republicans minimize special-election losses.

Republicans have said that the Democrats’ wins in special elections — when turnout is typically lower than normal — reflect a natural regression after their big gains in 2024 in Washington, D.C., and in state capitols across the country.

And success in special elections does not necessarily translate into victories in general elections. In January 2024, a Democrat captured a State House seat in Florida, only to lose it in a rematch in November.

Republicans also note that in the third state legislative special election on Tuesday, Hilary Holley, a 37-year-old Republican who leads a statewide agricultural association, defeated Edwin Perez, 66, a retired small-business owner, to represent a rural district between Tampa and Orlando. Ms. Holley won by almost 10 percentage points; the previous state representative, Josie Tomkow, won by almost 14 percentage points in 2024.

Is Florida in play?

The balance of power will not change anytime soon in Tallahassee, even if Mr. Nathan prevails. Still, the newest legislators will be involved in passing a budget before the July 1 deadline. They will also be on hand for a special session in April, called by Mr. DeSantis, to redraw Florida’s U.S. House map in time for the 2026 midterms.

Then comes November. Ms. Gregory and Mr. Nathan are expected to run again in the general election for a full two-year term, and they could face rematches against their Republican opponents.

Republicans hope that races for Florida governor and U.S. Senate draw out voters who did not show up for Tuesday’s special elections.

Democrats insist Florida is back in play, as it was when Barack Obama won it in 2008 and 2012. In a call with reporters on Wednesday, Ms. Gregory and Nikki Fried, the chairwoman of the Florida Democratic Party, said that Democrats were focused on pocketbook issues and better able to relate to regular Floridians.

Ms. Fried singled out two counties in northeastern Florida, Clay and Duval, which is home to Jacksonville, as places where Democrats were particularly bullish.

“If we can win in Donald Trump’s backyard, we can win anywhere,” Ms. Fried said.

David W. Chen is a Times reporter focused on state legislatures, state level policymaking and the political forces behind them.

The post Four Things to Know About a Democrat’s Win in Trump’s Backyard appeared first on New York Times.

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