Democrats sent a race-baiting text message depicting Black Republican Jon Maples in front of a rundown motel – and the group behind it was tied to his Democratic opponent.
Now Emily Gregory is headed to Tallahassee to represent the district that includes Mar-a-Lago.
Here's what Democrats did to win Trump's backyard – and why Republicans need to understand exactly how it happened.
The Play That Flipped Trump's District
In the final days of the race, Palm Beach County voters received a text message that Florida House Speaker-designate Sam Garrison called a "13 on a scale of 10" for disgusting campaign tactics.
The text showed Republican Jon Maples – a Black man – digitally placed in front of a rundown motel.
It was a racially charged smear built to make Maples look like a RINO and suppress Republican turnout.
The group that sent it was tied directly to Democratic candidate Emily Gregory's campaign vendor.
Garrison said he was "stunned" – and that it was done with the "tacit knowledge" of Gregory's campaign.
No apology came from Gregory.
She won anyway.
51% to 49% – in a district Trump carried by roughly 9 points in 2024 and where Republican Mike Caruso won re-election by 19 points that same cycle.
https://twitter.com/EricLDaugh/status/2036589399215944180?s=20
First time a Democrat has won House District 87 this century.
Now here's the part the media is burying: the vacancy only existed because Ron DeSantis appointed Caruso as county clerk and comptroller in August, leaving the seat empty for seven months.
Gregory sued over the delay.
DeSantis blinked, scheduled the election – and handed Democrats their rallying cry on a silver platter.
Democrats Are Running This Playbook Everywhere
Democrats didn't stumble into this win.
They built a machine – dark money, race-baiting voter suppression dressed up as opposition research, and first-time candidates who've never held office but know how to talk about grocery bills.
That's the template Gregory ran.
It worked.
And Florida wasn't a one-off: this is the tenth GOP-held state legislative seat Democrats have flipped since Trump returned to the White House, in districts from Louisiana to Texas to Wisconsin.
Republicans have flipped zero Democratic seats in return.
The party that never shuts up about protecting democracy paid – in Garrison's words – criminal defense lawyers to send race-baiting texts against a Black Republican, then collected the win without a word of remorse.
Across state legislative special elections since January 2025, Democrats have shifted results an average of 5.6 points in their favor, according to Ballotpedia data – winning 67 of 96 contested races to Republicans' 29.
Republicans in Florida still hold a 1.48 million-voter registration edge statewide.
https://twitter.com/MeidasTouch/status/2036593745257439418?s=20
Special election turnout is low by design – and Democrats are weaponizing that, targeting exactly the kind of off-cycle race where an organized dark-money operation can move results before anyone's paying attention.
Here's what the media won't tell you: DeSantis, the FHRCC, and the Palm Beach County Republican Party handed Democrats every advantage in this race – the long vacancy, the awkward timing, the dark-money attacks on their own candidate going unanswered.
And Democrats still only won by two points.
Gregory didn't run away with Trump's backyard.
She scraped past the finish line using tactics that would end a Republican's career across every front page in America.
That's not a movement.
That's desperation with a $1 million war chest and no shame – and Republicans need to be ready for it in every district this November.
Sources:
- Caroline Vakil, "Democrats flip Florida state House district that includes Trump's Mar-a-Lago," The Hill, March 24, 2026.
- Florida Politics, "Democrat Emily Gregory wins Special Election for HD 87 in Palm Beach County," Florida Politics, March 24, 2026.
- Florida Politics, "Group tied to Emily Gregory sends race-baiting text; Dems should condemn it," Florida Politics, March 19, 2026.
- Florida Politics, "Speaker-designate Sam Garrison 'stunned' by racist campaigning in HD 87," Florida Politics, March 20, 2026.
- Ballotpedia News, "State legislative special elections show shift toward Democrats compared to previous regular elections," Ballotpedia, February 26, 2026.
- Palm Beach County Supervisor of Elections, official results, March 24, 2026.
