Florida Special Elections: A Crucial Test for Democrats

Democrats in Florida are focusing on a special state House election for District 87, which encompasses President Donald Trump’s Mar-a-Lago residence. The election, scheduled for Tuesday, presents an opportunity for Democrats to secure a win in a traditionally Republican stronghold. Emily Gregory, a first-time candidate and small business owner, is challenging Republican Jon Maples, who has received Trump’s endorsement. The seat became vacant after former Republican state Rep. Mike Caruso was appointed as Palm Beach County clerk and comptroller. Trump won the district by approximately 11 points in the 2024 presidential election, yet the county narrowly supported former Vice President Kamala Harris.

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Both candidates are emphasizing affordability, a key issue that has resonated with voters in recent elections. Gregory has stated her intention to focus on the needs of the over 180,000 residents in her district, attempting to minimize the influence of Trump’s presence in the race.

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Simultaneously, a special election for Senate District 14 in Hillsborough County is drawing attention as both parties assess the political landscape ahead of the 2026 midterms. Democrat Brian Nathan is running against Republican state Rep. Josie Tomkow. Although the district leans Republican, Nathan's campaign aims to capitalize on dissatisfaction with current issues, including affordability and low approval ratings for Trump. Voter registration data indicates a Republican advantage, with GOP voters comprising nearly 39% of the electorate compared to 31% for Democrats.

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Despite the odds, Nathan has garnered support from several unions and has raised less than $65,000 for his campaign, significantly less than Tomkow’s reported $3 million. Early voting data suggests a Republican lead, but Democratic strategists are closely monitoring independent voter turnout, which could influence the election outcome.

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Both elections are critical for the Democratic Party as they seek to maintain momentum following recent successes in special elections across the country. A win in either district would not only bolster Democratic representation but also serve as a barometer for voter sentiment leading into the midterms. Recent trends indicate that Democrats have been able to mobilize voters effectively, which could signal challenges for Republicans in upcoming elections.

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The Democratic Legislative Campaign Committee has expressed support for Gregory, highlighting her as a candidate capable of connecting with voters. Meanwhile, Trump has publicly endorsed Maples, praising him as a successful businessman and civic leader. The contrasting endorsements reflect the high stakes of these elections for both parties.

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While early voting data shows a Republican advantage in both districts, the potential for Democratic overperformance remains a point of contention. Some analysts suggest that if Nathan can attract a significant portion of independent voters, he could narrow the gap against Tomkow. However, prediction markets currently favor Tomkow, indicating a 94% chance of her victory.

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“Jon is a very successful Businessman and Civic Leader, who is known and loved,” — Donald Trump, Former President

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“But it also shows signs of hope for Democrats, who, even if they don’t win, could walk away from Election Night feeling good about their prospects in November if Nathan overperforms.” — Political Analyst

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“exactly the kind of candidate who can defy the odds and connect with voters as a small business owner and mom” — Heather Williams, DLCC President

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The outcomes of these special elections will be closely monitored as indicators of the political climate in Florida and the broader national landscape heading into the 2026 midterms.

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