Tuesday, March 24, 2026

BREAKING: Florida Democrats flip Donald Trump's home district in Palm Beach

                                                                                                            

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More than a month ago, we called your attention to an unusual special election:

Morning Digest: The next big special election is happening in Trump's backyard

Morning Digest: The next big special election is happening in Trump's backyard

·
Feb 18
Read full story

Well, it did indeed turn out to be big—very big indeed, as we explain in our breaking news alert below.

No other outlet covers special elections as closely as we do, and we do so for a very important reason: They can tell us a lot about the political environment today and how it might look come November.

If you appreciate being the first to know about critical races like this one, then we hope you’ll consider supporting our unique work by upgrading to a paid subscription today. We ask for just $7 a month or a heavily discounted $60 a year.

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The Downballot team


BREAKING: Florida Democrats flip Donald Trump's home district in Palm Beach

Emily Gregory will now represent Mar-a-Lago—and Trump himself


Florida Democrat Emily Gregory, second from left (Emily Gregory campaign site)

Florida Democrat Emily Gregory scored a major upset on Tuesday night, flipping the legislative district that includes Donald Trump’s waterfront lair of Mar-a-Lago.

Gregory, a first-time candidate who runs a fitness business serving pregnant and postpartum women, defeated her Republican opponent, financial planner Jon Maples, by a 51-49 margin to win the 87th House District in Palm Beach County.

The race for this slice of the South Florida beachfront was both caused by and delayed by Gov. Ron DeSantis, who appointed one of his few loyalists in the state legislature, Rep. Mike Caruso, as Palm Beach County clerk to fill a vacancy last August.

As he often has in the past, though, DeSantis refused to call a special election, very possibly because he feared how it might turn out. Only after Gregory filed a lawsuit did he finally act, nine weeks after Caruso resigned.


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If DeSantis was worried, he was right to be. Even though Republicans poured resources into the race and outspent Democrats by a wide margin, it wasn’t enough to save Maples, who earned Trump’s endorsement in January.

Trump also cast a ballot—presumably for Maples—and he did so by mail.

"Mail-in voting means mail-in cheating. I call it mail-in cheating, and we got to do something about it all," Trump said at an event on Monday. For weeks, he has demanded that Congress pass legislation mandating “NO MAIL-IN BALLOTS EXCEPT FOR MILITARY - ILLNESS, DISABILITY, TRAVEL.”

Trump experienced a surge in popularity in his own backyard in his last election, but it appears to have been temporary. In 2020, he carried the 87th District by just a hair, 49.8 to 49.3. Four years later, by contrast, he jetted out to a 55-44 win, while Caruso prevailed by an even wider 59-41 margin in his final reelection campaign.

Gregory, though, overcame that deficit by emphasizing her plans to address the soaring cost of living, particularly the skyrocketing cost of property insurance in this environmentally vulnerable coastal community.

Notably, she prevailed even though registered Republicans accounted for about 46% of the electorate, with Democrats making up 36% and independents 18%.

Republicans will still retain their supermajority in the state House, but Gregory’s victory offers a much-needed boost to Florida Democrats, who are hoping for similar upsets in even higher-profile contests on the November ballot. They’ll also have the chance to break the GOP’s supermajorities in both chambers of the legislature.

And they’ll take a measure of satisfaction in knowing that the state’s most famous resident is now represented by a Democrat.

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Today in Politics, Bulletin 339. 3/30/26

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