Seven years after officially decamping to his Palm Beach estate from New York, President Donald Trump will be represented by a Democrat in the Florida statehouse for the first time.

Emily Gregory, a small-business owner and first-time candidate, notched an upset win on Tuesday evening, defeating the Trump-backed nominee Jon Maples to flip Florida House District 87, a long-standing Republican state legislative district that contains Trump’s Mar-a-Lago estate. Gregory received 51 percent of the vote to Maples’s 48 percent in the district, which spans Palm Beach, Lantana, and Jupiter, among other towns.

Gregory’s victory likely comes with a bit of a personal sting for Trump. The president issued a full-throated endorsement of Maples on Monday, calling him a “very successful Businessman and Civic Leader” and urging Floridians to head to the polls to support him. And county records show that Trump voted in the special election via mail ballot, just days after he revived his frequent complaint that mail-in voting constitutes “cheating.”

The seat has been vacant since last August, when former Republican state representative Mike Caruso was tapped by Governor Ron DeSantis to serve as Palm Beach County clerk. In 2024, Caruso won reelection to the seat by 19 points over his Democratic challenger, a sign of the party’s traditional hold over the area. That same year, Trump carried the district by 11 points during his presidential bid.

But Gregory was not an outlier on Tuesday. As of Wednesday morning, Democrat Brian Nathan is leading in a special election for a Tampa state-senate district, a seat left open after DeSantis appointed its previous holder, Jay Collins, as his new lieutenant governor.

The Democratic Party has had a string of successes with special elections this cycle, winning red districts in Arkansas, Texas, and New Hampshire. The party was quick to tout Gregory’s win as a sign of its strength as the midterms approach. “Mar-a-Lago just flipped red to blue, which should have Republicans sweating the midterms. A Trump +11 district in his own backyard shouldn’t be in play for Democrats, but tonight proves Republicans are vulnerable everywhere,” Democratic Legislative Campaign Committee president Heather Williams said in a statement. “If Mar-a-Lago is vulnerable, imagine what’s possible this November.”

In an interview with MS NOW shortly after the race was called, Gregory said she was still “pretty shocked” about the result. When asked about Trump now being one of her constituents, the incoming state representative appeared unfazed.

“I mean, I don’t think all of that much about it. He’s one of 115,000 registered voters in District 87. My opponent made him forefront in his campaign, and I focused more on the voters in District 87 — what everybody needs, what all of us will do better with: with lower property insurance, with expanded health care, and with strong public schools,” she said.

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