Summary (tl;dr)

Democrat Emily Gregory has won a special election for Florida House District 87, flipping a reliably Republican seat that includes former President Donald Trump's Mar-a-Lago estate, signaling potential momentum for Democrats ahead of the 2026 midterm elections.

Essential Background

The special election for Florida House District 87 was called after Republican Mike Caruso resigned from his seat in August 2025 to become the Palm Beach County Clerk and Comptroller. This district, which encompasses coastal areas of Palm Beach County, has historically leaned Republican, with Caruso winning by 19 percentage points in 2024 and President Trump carrying the district by approximately nine points in the same year. The race featured Democrat Emily Gregory, a first-time candidate, against Republican Jon Maples, who received an endorsement from former President Donald Trump.

The Full Story

Emily Gregory secured an upset victory on March 24, 2026, winning 51.15% of the vote against Jon Maples' 48.85%, marking the first time a Democrat has won this district this century. The election garnered national attention, partly due to President Trump's residence, Mar-a-Lago, being within the district, and his active endorsement of Maples. Gregory's campaign focused on local issues such as increasing public education funding, expanding healthcare access, and addressing rising property insurance and housing costs. The lengthy vacancy in the seat, due to Governor Ron DeSantis's delay in calling the election, prompted Gregory to sue, arguing that constituents were denied representation during the 2026 Legislative Session.

Why It Matters

Gregory's victory is seen by Democrats as a significant indicator of voter sentiment and potential momentum leading into the 2026 midterm elections, suggesting a broader turning away from former President Trump and the Republican party. National Democratic leaders have highlighted the win in Trump's "backyard" as a "crystal clear message" that voters are frustrated with rising costs and are ready for change. This win represents the 29th legislative seat Democrats have flipped from Republican control since Trump took office, emphasizing that even in traditionally red districts, Republicans may be vulnerable.

Geographic Location

• Florida House District 87 (special election held, encompassing Palm Beach Gardens, Jupiter, Juno Beach, Hypoluxo, and Mar-a-Lago), Palm Beach County, Florida, United States (Democrat Emily Gregory won a special election)
• Tallahassee, Leon County, Florida, United States (impact of legislative vacancy during the 2026 Legislative Session)