Democrats Score Upset Victories In Two Special Elections In GOP Stronghold

Florida Democrats secured a pair of special election victories on Tuesday.

Democrat Emily Gregory defeated Republican Jon Maples in a special election in Florida’s House District 87, a Palm Beach-area district that includes Mar-a-Lago.

The race was to fill the seat left vacant last August after Republican state Rep. Mike Caruso resigned to become Palm Beach County clerk and comptroller.

“Trump carried this district by 11 points in 2024,” Decision Desk HQ noted.

Tonight has seen several close elections in Florida.

In State House District 87 – home to Mar-a-Lago – Democrat Emily Gregory is projected to defeat Republican Jon Maples.

Trump carried this district by 11 points in 2024.https://t.co/52LoigPiR9 pic.twitter.com/RSSvv81uUD

— Decision Desk HQ (@DecisionDeskHQ) March 24, 2026

Fox News has more:

The ballot box battle was one of three special legislative elections being held in GOP-dominated Florida on Tuesday. And while the contests won’t change the balance of power in the state legislature, where for more than a quarter-century Republicans have held majorities in both the House and Senate chambers, bragging rights were up for grabs in the president’s home district.

Maples was backed by Trump, who moved his primary permanent residence in 2019 from Trump Tower in New York City to Mar-a-Lago in Palm Beach, Florida. He is also backed by a number of top Sunshine State Republicans.

“There is a very important Special Election tomorrow, Tuesday, March 24th, for Florida State House District 87 in beautiful Palm Beach County — JON MAPLES HAS MY COMPLETE AND TOTAL ENDORSEMENT!” the president wrote in a social media post on Monday evening.

The 43-year-old Maples, a financial planner and former Lake Clarke Shores Council member who, during his years at Palm Beach Atlantic University was an all-American athlete, made cutting taxes and government spending, reducing regulations, promoting private sector job creation and advancing school choice a priority.

Gregory, a 40-year-old Army spouse, owns and runs a Jupiter-based fitness center for pregnant and postpartum women. The first-time candidate made affordability, increasing public education, tackling rising property insurance and housing costs, and access to healthcare key parts of her campaign.

Maples was the favorite heading into the special election, thanks to his fundraising advantage in a district that leads to the right. Trump carried the district by roughly 10 points in his 2024 re-election victory. And Caruso won re-election in the district by 19 points.

Another Democrat victory came in the Tampa area to fill a state Senate seat.

“Democrat Brian Nathan, a Navy veteran and union leader, defeated Republican state Rep. Josie Tomkow to helm Florida Senate District 14, which includes part of Hillsborough County,” The Hill reports.

“Donald Trump carried this seat by 7 points in 2024,” Decision Desk HQ stated.

In State Senate District 14. Democrat Brian Nathan leads Republican Josie Tomkow by around 600 votes with almost all votes counted.

Donald Trump carried this seat by 7 points in 2024.https://t.co/35XeHdiRBy pic.twitter.com/8qJqKFYxo0

— Decision Desk HQ (@DecisionDeskHQ) March 24, 2026

The Hill noted:

Florida Lt. Gov. Jay Collins (R), now a candidate for governor, held the seat before he was tapped by Florida Gov. Ron DeSantis (R) to serve as his second in command.

In 2022, Collins defeated Democrat Janet Cruz by 9 percentage points, while the entire county narrowly went for President Trump in 2024 by 3 points.

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