In a stunning political upset, Democrat Emily Gregory has flipped a deeply conservative Florida state House district that includes Mar-a-Lago, the longtime residence of Trump.
Gregory narrowly defeated Trump-endorsed Republican Jon Maples in a special election for Florida’s 87th district, winning by roughly two percentage points in a race few Democrats were expected to seriously contest.
“When we started this, nobody thought it was possible. They thought we were crazy,” Gregory said to her supporters at her election night party. “I knew my community. I knew we deserved better. We deserve a leader who will fight for us.”
The result marks a dramatic reversal in a district that had comfortably favored Republicans in recent elections, with the previous GOP candidate winning by nearly 20 points in 2024. Political observers say the outcome underscores growing volatility ahead of the 2026 midterms, particularly as Democrats continue to notch unexpected gains in traditionally red areas.
The symbolic weight of the victory is hard to overstate: a district that includes Trump’s own backyard—and where he actively urged voters to support his preferred candidate—has now flipped blue. Democratic strategists quickly seized on the result as evidence that even strongholds once considered safely Republican are now competitive. Her win is already being framed as a warning sign for Republicans heading into November, and a potential bellwether for shifting political winds nationwide.
Meanwhile, while Trump wants voting by mail to be ‘illegal,’ he did a mail-in vote for the Florida Republican.
