Democrats flipped a Florida State House seat Tuesday night that comfortably backed President Donald Trump in 2024 and also happens to include his Mar-a-Lago residence.
Democrat Emily Gregory beat Trump-endorsed Republican Jon Maples in the president’s home seat, which he carried by double digits during his successful reelection run. On the same night, Democrats appeared poised to flip a Tampa-based State Senate seat while Republicans held another State House seat in a more rural and conservative part of the state.
Sunshine State voters went to the polls for special elections in one state Senate and two state House districts, which became vacant due to a series of appointments by Republican Florida Gov. Ron DeSantis.
Gregory won 51.1% of the vote to Maples’ 48.9%, with over 95% of the vote counted, according to the Associated Press. She will succeed former Republican Florida State Rep. Mike Caruso, who resigned from House District 87 in August 2025 after DeSantis appointed him Clerk of the Circuit Court and Comptroller of Palm Beach County. More than a combined $1 million dollars had been spent between both candidates in the hotly contested special election.
Gregory is a mother of three and Army wife who owns a fitness business for pregnant and postpartum women, according to her campaign website. Her profile on the Democratic Legislative Campaign Committee’s website describes her as a “small business owner and public health professional.” The Democrat heavily emphasized affordability and cost of living— issues that have spurred Democratic election victories in recent months — during her successful run for office.
“An Army spouse and mom of three young boys, Emily knows the challenges Florida families face-from rising costs to limited support for working parents,” Gregory’s website states. “She’s ready to bring her experience and values to Tallahassee to fight for a healthier, more affordable Florida where families can thrive.”
Maples, a former member of the Lake Clarke Shores Town Council, meanwhile received a last-minute endorsement from Trump himself — a rare feat for a state legislative candidate.
“Jon is a very successful Businessman and Civic Leader, who is known and loved, and also endorsed by so many of my Palm Beach County friends, including by Great State Representative ‘MAGA’ Meg Weinberger. Jon will be a terrific Legislator!” the president wrote on Truth Social late Monday.
Texas Republican Leigh Wambsganss, whom Trump similarly endorsed for a state-level race, lost an early February Texas State Senate special election to a Democrat, also in a seat the president carried by double digits in 2024.
District 87 straddles the Atlantic coast and includes Palm Beach — where Trump’s estate sits — as well as North Palm Beach, South Palm Beach and a portion of West Palm Beach. Trump won it by nearly 11 percentage points in 2024, but carried it by razor-thin margins during his other two runs for the presidency, according to data on Dave’s Redistricting App (DRA).
Mar-a-Lago’s most famous resident won the district, including his club and resort. by just half a percentage point in 2020 and by a mere 33 votes in 2016, per DRA data. It voted for DeSantis by a landslide margin of 16.5 points in the 2022 gubernatorial election but supported his Democratic opponent Andrew Gillum by less than a point four years earlier.
Hits close to home….
The seat that Ms. Gregory won had been held by a Republican who won by 19 percentage points in 2024!
Florida Democrats Win Special Election in Mar-a-Lago’s District https://t.co/IFsuDy2iTs via @NYTimes
— Amy Klobuchar (@amyklobuchar) March 25, 2026
Should Democrats continue to target seats in traditionally Republican areas like Florida's District 87?
National Democrats including Minnesota Sen. Amy Klobuchar celebrated Gregory’s win on X.
“Donald Trump’s own neighbors in Florida just sent a message: They elected a Democrat, Emily Gregory, to serve as their representative in the Florida state House,” Democratic National Committee Chair Ken Martin wrote on the platform Tuesday night. “If Democrats can win in Trump’s backyard, we sure as hell can win anywhere across the country. Onward to November!”
About 200 miles from Palm Beach, a State Senate special election between Democrat Brian Nathan and 30-year-old Republican State Rep. Josie Tomkow remains too close to call per the AP, with Nathan narrowly leading. Decision Desk HQ, however, has called the race for the Democrat.
The Tampa-area Senate District 14, which Trump won by over seven points in 2024, was last held by Republican Florida Lt. Gov Jay Collins, whom DeSantis appointed in August 2025.
Not official yet, but Florida Democrats are on the verge of their best night in nearly 14 years.
They’re poised to flip a Trump+7 State Senate seat and a Trump+11 State House seat in the same night. https://t.co/ZLoRYMxUIs
— Zachary Donnini (@ZacharyDonnini) March 24, 2026
According to his campaign website, Nathan is “a proud Navy veteran and dedicated union leader” and a member of the International Brotherhood of Electrical Workers — making him the second member of his party with a military and labor background to flip a red-leaning State Senate seat in the past two months. Democratic Texas State Sen. Taylor Rehmet, who defeated Wambsganss in February, is also a military veteran and union leader.
Republicans held Tomkow’s State House seat, which Trump won by 13.6 points in 2024, as GOP nominee Hilary Holley easily defeated Democrat Edwin Pérez by an eight-point margin, according to the AP.
Tuesday’s election results represent a remarkable turnaround for the Florida Democratic Party which, less than a year ago, saw its state Senate Leader Jason Pizzo quit his role, register as an independent and declare the state party affiliate “dead.” An anonymous Florida Democrat told Politico in May 2025 that the state party was “such a goddamn shitshow.”
Nevertheless, DeSantis still holds strong GOP supermajorities in both houses of the Florida Legislature, heading into the midterms.
Even with the addition of Gregory, Democrats still control only 34 of the Florida State House’s 120 seats — accounting for 28% of seats, despite former Vice President Kamala Harris winning 43% of the vote in the Sunshine State in 2024. Assuming Nathan’s lead holds, Democrats will similarly control only 12 of 40 State Senate seats — just 30%.
In addition to the seats in Florida and Texas, Democrats have won special elections in seats Trump won by over 10 points in Georgia, Iowa and Pennsylvania, since the president began his second term in office.
This is a breaking news story and will be updated.
(Featured Image Media Credit: Screen Capture/CNN)
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