Emily Gregory, a first-time candidate and business owner, won the special election for Florida's 87th District on Tuesday, beating Trump-endorsed Republican Jon Maples 51% to 49% and flipping a seat that includes President Trump's Mar-a-Lago resort. The Associated Press called the race for Gregory, marking the tenth GOP-held state legislative seat Democrats have flipped nationwide since Trump began his current term.

Trump carried the district by about 11 percentage points in the 2024 election, according to The Downballot. He personally cast a ballot in the special election and backed Maples in both the special primary and the special general, urging social media followers to turn out. It wasn't enough.

What Happened in Palm Beach County

The seat had been vacant since August, after Palm Beach County Clerk Mike Caruso resigned from the legislature and was appointed to his current office. Gregory's campaign focused on rising costs, promising to prioritize the issue if elected. Maples, a former council member in Lake Clarke Shores, touted his business experience and pledged to cut taxes.

According to NBC News,  A two-point margin in a district Trump won by double digits is the kind of result that gets national attention, and Democrats will make sure it does. The race was one of three legislative special elections on ballots across Florida on Tuesday, with a fourth decided by default after the Republican candidate ran unopposed. In the Tampa area, Democrat Brian Nathan was leading Republican Josie Tomkow for a state Senate district previously held by the GOP, though that race remained too close to call. Republican Hilary Holley held a state House seat in Central Florida for her party.

The Pattern That Matters

Ten flipped seats is a number worth taking seriously, even if special elections are imperfect barometers of broader political sentiment. Low-turnout races reward enthusiasm, and right now the enthusiasm gap favors Democrats in certain pockets of the country. That's a tactical problem, not an existential one, but it's a problem Republicans ignore at their peril.

The more interesting question is why. Most public polling places Trump's approval rating in the high-30s to the low-40s, and the war with Iran has dominated media coverage for a month. Special elections in off-cycle windows tend to attract voters with a grievance, and the party out of power at the federal level almost always has a deeper well of grievance to draw from. This is the mirror image of what Republicans did to Democrats throughout 2021 and 2022 in Virginia, in school board races, and in state legislative contests across the country.

None of that means the underlying political landscape has fundamentally shifted. It means Democrats are showing up for low-profile races and Republicans, in some of these districts, are not. The cure for that is straightforward: show up.

The Cost of Complacency

Gregory's victory is a reminder that endorsements, even presidential ones, do not substitute for candidate quality and ground-game execution. Maples ran on tax cuts and business experience. Gregory ran on kitchen-table costs. In a district where voters are watching grocery bills and insurance premiums climb, the candidate talking about what hurts right now edged out the candidate talking about what might help eventually.

Republicans in Florida have enormous structural advantages. The state's legislative supermajorities are not in danger from a handful of special election losses. But complacency is how structural advantages erode. Every seat flipped in a low-turnout special becomes a Democratic incumbent with name recognition, constituent services, and a fundraising base heading into the next cycle.

The Florida GOP should treat this as a fire alarm, not a house fire. The building isn't burning. But the smoke is real, and the people smelling it are the voters Republicans assumed would always be there.

Ten seats in one cycle. The eleventh will be easier than the first.