Battle in Mar-a-Lago's backyard threatens brutal wake-up call for Trump

Mar-a-Lago — President Donald Trump’s luxury “winter White House” private club and residence — sits in a narrowly drawn Florida state house district hugging the Palm Beach coast.

That strip represents one of the target districts where Democrats are hoping to send their latest message to Republicans and Trump, who faces a tanked approval rating, through a small business owner they hope can flip the seat in Florida House District 87.

The Democratic Legislative Campaign Committee (DLCC) boasts 28 state-level flips so far – and none for Republicans — since Trump was elected.

“This is a stark reminder that Democrats are not just winning in blue states or even in competitive districts. We are winning in red communities, and we're putting up a fight right in the president's backyard,” Heather Williams, DLCC president, told Raw Story.

“There's some groundswell opportunity there. This is also in the kind of district that we've been winning. We have been marching into Republican territory. We've been flipping seats, and we're leaving no stone unturned when it comes to that.”

The March 24 special election squares off Democrat Emily Gregory, a public health expert and Fit4Mom Palm Beach owner, against Jon Maples, a financial adviser and former All-American college athlete endorsed by Trump.

Emily Gregory (Photo courtesy of Emily Gregory for Florida)

“When people are given the option of a very extreme, far right-wing option or a pragmatic Democrat, I think they will choose the pragmatic Democrat,” Gregory told Raw Story.

“When we will win, it will send an incredibly powerful message to Democrats statewide and nationally.”

Maples and the Republican State Leadership Committee did not respond to Raw Story’s request for comment.

'Outcry and outrage'

After Florida Gov. Ron DeSantis appointed Mike Caruso, the incumbent Republican state representative for the district, to serve as Palm Beach County Clerk in August 2025, he failed to call a special election for months until after Gregory filed a lawsuit alleging the governor did not following state law.

Without representation for an entire legislative session, “people are really understandably outraged,” Gregory said.

Gregory said she’s campaigning on “pragmatic solutions” to address the affordability crisis and state housing issues.

When she knocks on doors, Gregory said voters talk about skyrocketing property insurance rates, access to affordable health care and funding public schools.

“More recently, we've really been hearing this outcry and outrage at democracy in peril,” Gregory said.

Residents in the district are concerned about the Trump administration’s aggressive handling of immigration enforcement that left protesters dead when U.S. Immigration and Customs Enforcement (ICE) sent thousands of federal agents to Minnesota.

“No one is okay with armed thugs being out in the streets, shooting American citizens,” Gregory said.

“No one is okay with the unregulated militia that is ICE.”

Emily Gregory (Photo courtesy of Emily Gregory for Florida)

State legislators are in charge of the drawing of congressional maps, and at least one-third of states have proposed redrawing maps since Republicans started a mid-decade gerrymandering war at the urging of Trump.

The winner of the Florida House District 87 race will participate in Florida’s April special session on congressional redistricting, said Gregory, who is against mid-decade redistricting.

“There's a lot to be fearful of in this power grab,” Gregory said.

“We have to maintain our civic duty and our decade pattern, and I think trying to do it halfway through the decade just shows how desperate the current administration is, and the implications of losing those congressional seats would be profound.”

Democrats hope their successes at the state-level are a bellwether for the November midterm elections when they look to take back control of the U.S. House of Representatives and even possibly the U.S. Senate.

The major super PAC for Senate Republicans skyrocketed their dark money contributions in order to protect their GOP majority, Raw Story first reported.

“If I were Republicans, I'd be deeply concerned about this. They benefited from this kind of environment in 2010, and we're knocking on the same door, only in the opposite direction this time, where we've got this incredible opportunity and we are ready to show up and meet the needs of voters across the country,” Williams said.

“Regardless of what the national narrative is like, Democrats can win elections, and we can win elections when we meet voters where they are and with a D behind our name.

“I think that's incredibly important as we think about officially now, transitioning into primary season, and how we think about winning up and down the ballot.”