First-time candidate Emily Gregory flipped a seat in a district that includes President Trump’s own Mar-a-Lago estate in a special election on Tuesday.

Gregory won her seat in the Florida House of Representatives after running a campaign focused on the ongoing affordability crisis.

The Democratic Party described the result as an “earth shattering victory for Florida Democrats.”

The seat had previously been held by former GOP State Representative Mike Caruso, who resigned after he was appointed as a county clerk by Governor Ron DeSantis.

In winning Florida’s House District 87, Gregory defeated Republican Jon Maples, whom Trump had endorsed in a Truth Social post.

Who is Emily Gregory?

Gregory was born on Florida’s Treasure Coast, according to her website. She grew up in Stuart, a city which is just 20 miles from the town of Jupiter, where she now lives.

The 40 year-old is a mother of three, Catholic and small business owner.

She holds two degrees, a BS in Health and Exercise Science from Wake Forest University and a Master of Public Health in Health Policy and Management from Columbia University.

The Democrat runs FIT4MOM Palm Beach, a fitness community that aims to support pregnant and postpartum women. Through her business, Gregory offers a range of classes, including 60-minute workouts named Stroller Strides.

Her other classes focus on improving posture and building her clients’ confidence, according to the FIT4MOM website.

Who is Emily Gregory’s husband?

In December 2025, Gregory revealed on Instagram that her husband Andrew had been promoted to the position of Lieutenant Colonel in the U.S. Army.

“Congratulations, LTC Gregory,” she wrote. “We are so proud of you and your service to our nation.”

Gregory often referred to her husband’s career on the campaign trail, dubbing herself an “army spouse.”

In early March, she made a reference to her husband’s career in a Facebook video thanking VoteVets.org for their endorsement.

“As a military spouse, I know that service is a team sport,” she said, before pledging to fight for lower property insurance and expanding healthcare.

The couple share three children, who have been featured prominently throughout the latter’s House seat campaign.

On November 1, 2025, Gregory posted an image on Instagram showing her family dressed up as characters from Star Wars for Halloween.

Gregory was dressed as the franchise’s heroine, Princess Leia, while her sons and husband were dressed as other heroes and villains from Star Wars.

“Happy Halloween from a galaxy far, far away,” she captioned the post.

What does Emily Gregory believe?

Although she did criticise Trump in her recent campaign, Gregory focused much of her House bid on the ongoing cost-of-living crisis.

“I think my opponent put it front and center, and I focused on the issues that matter most to Florida families,” Gregory told CNN.

“Everyone is feeling the affordability crisis, and the last thing that Florida families needed when they’re struggling is $4 gas.”

However, Gregory told the network that she is “happy” to speak to Trump, whose gilded Mar-a-Lago estate lies within the boundaries of her district.

On her website, Gregory said that she had experienced many of the same problems as others in her community, including rising costs and limited access to affordable healthcare.

Gregory has repeatedly waded into debates over schooling in Florida, calling for greater investments into educational institutions on her Facebook page.

The Democrat has also shared on social media that she was “deeply concerned about efforts to eliminate vaccine mandates” in the state’s schools.

“Removing these safeguards puts vulnerable children at serious risk and turns classrooms into potential outbreak sites,” she added.