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CNN’s Harry Enten Reveals What Democrats’ Stunning Mar-A-Lago Flip Means For Midterms

Screenshot/Rumble/CNN

CNN senior data analyst Harry Enten said a Democrat’s stunning flip of a red Florida State House seat that includes Mar-a-Lago signals a broader trend suggesting November’s midterms could be a blue wave.

Democratic candidate Emily Gregory bested Trump-endorsed Republican Jon Maples in a major upset Tuesday night, winning a special election to become the president’s state representative. During an appearance on CNN’s “Erin Burnett OutFront” that same night, Enten said Gregory’s two-point victory was “emblematic” of a “massive shift” from fewer than two years ago, when the South Florida district’s most famous resident carried it by double digits in the 2024 presidential election.

“In a district that [President] Donald Trump won by 11 points. That is a massive shift, right?” Enten asked host Erin Burnett. “That is a double-digit shift towards the Democrat.”

“And what I will say, what is so important, It is happening now in Donald Trump’s backyard, but it has been happening across the country. We have seen these massive shifts in these special elections,” the CNN data analyst continued. “I looked at all of them. So far to date, the state legislative, the federal special elections.”

“No matter what it’s for? Any special election?” Burnett asked for clarification.

“Correct. For state legislative or federal for Congress,” Enten said. “And what we’ve seen so far is a shift to the Democrats on average of 12 points. We have seen a shift of 12 points from the Kamala Harris baseline from what we saw. … It’s emblematic, Erin, of what we’ve seen nationwide.”

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Since Trump began his second term, Democrats have picked up a host of state legislative seats Trump carried by double digits in 2024, including those in Florida, Texas, Georgia, Iowa and Pennsylvania. The party has also over-performed expectations in many state and federal special elections, including ones where it came up short, such as the December 2025 race for Tennessee’s Seventh district.

Burnett then asked Enten what this all means for the midterm elections.

“There’s a reason we’re talking about this, and it’s not just because it’s in Donald Trump’s backyard, though. That’s part of the reason why. It is because, historically speaking, special elections have forecasted what will happen in the midterm elections,” the analyst said. “I went all the way back since I was in high school, back to the 2005-2006 cycle. And every single time that a party outperformed the presidential baseline in the next midterm election, what we saw was five out of five times that party went on to win the U.S.House of Representatives.”

“So, what is happening right now in Mar-a-Lago is unlikely to stay at Mar-a-Lago. It is likely to expand nationwide and to expand in the midterm elections as well,” Enten said.

Immediately before beginning her segment with Enten, Burnett interviewed Gregory, who was in her car on the way to her election night party. At the time, the race had yet to be officially called, although the Democrat was clearly leading.

“We’re feeling confident. What we’re confident in is that we were talking about the right issues, and we were knocking all of the doors and doing all of the things to get in front of voters and really hear their concerns,” Gregory told the CNN host. “And we heard over and over again, property, insurance, health care and education. And that’s what we focused on. And we’re feeling hopeful for tonight.”

Burnett also asked the Florida Democrat if Trump’s presence and Mar-a-Lago factored into the race.

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“For me, not so much. My opponent put it front and center, and I focused on the issues that matter most to Florida families,” Gregory responded, referring to defeated Republican candidate Jon Maples who received Trump’s “complete and total endorsement” on Truth Social the night before Election Day.

“Everyone is feeling that affordability crisis, and the last thing that Florida families needed when they’re struggling is $4 gas,” she continued, naming the issue that thus far has dominated the midterms. “So, that is what I spoke about, and that is what I talked to voters about, so it [Trump’s presence] wasn’t as much a factor for me, but perhaps my opponent focused on it.”

The CNN host also said the president is poised to be one of Gregory’s constituents and asked if she had anything to say to him.

“I would be happy to have a conversation. And you know, all 180,000 residents of District 87 are my priority if I’m so lucky to serve, so I will put them all with equal weight,” the Democrat answered.

Finally, Burnett asked Gregory how the president’s war on Iran affects her family, given that her husband is in the Army.

“We as a family are very concerned about another endless war. Of course, it’s outside the scope of the State House, but it does have personal ramifications for my family. So, I pray for our troops, and I pray for our family, and I hope a resolution comes sooner rather than later,” she said.

(Featured Image Media Credit: Screenshot/Rumble/CNN)