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President Trump woke up to a political gut-check Tuesday night as Democrats snatched a Florida state House seat right in his own backyard, according to election results from the Florida Division of Elections. Emily Gregory, a 40-year-old Army spouse and fitness center owner, defeated Republican Jon Maples in a special election for District 87—a Palm Beach district that literally includes Mar-a-Lago, Trump’s permanent residence. Maples wasn’t some random candidate either; the 43-year-old financial planner had Trump’s ‘complete and total endorsement,’ as posted by the president on Truth Social just a day before the election.
Trump carried this district by roughly 10 points in 2024, per data from the Florida Division of Elections, and the previous Republican representative won re-election by 19 points in the prior cycle. Yet Gregory still pulled off the upset. The Democratic National Committee immediately crowed about an ‘earthshattering victory’ and ‘humiliating defeat for Donald Trump,’ with DNC Chair Ken Martin stating in a press release, ‘Donald Trump’s own neighbors just sent a crystal clear message: They are furious and ready for change.’ Is this a sign of trouble brewing for Republicans in the midterms, or just a low-turnout special election fluke?
Gregory’s campaign focused on affordability—property insurance, housing costs, healthcare access—as detailed in her campaign materials. It’s the same playbook Democrats have been running in special elections since Trump returned to office, and it’s been working, based on analyses from Politico. Republicans downplayed the loss, with RNC Senior Adviser Danielle Alvarez calling it ‘a snapshot of local quirks, candidate dynamics, and turnout math—not some grand verdict’ in a statement to reporters.
But here’s what should worry the GOP: this isn’t an isolated incident, as reports from Fox News show Democrats have been overperforming in special elections across the country for months. The pattern is real. The question is whether Republicans can reverse it before November.
Providence watches over the bold.
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