Florida Man Loses Bigly

There is no joy in Trumpville after last night’s special elections in Florida.

The big loser in yesterday’s special Florida state legislative elections was Donald Trump. His personally endorsed candidate in House District 87, Jon Maples, lost to Democratic challenger Emily Gregory.

Unfortunately for Trump, this wasn’t the GOP’s only loss in the state. In Florida Senate District 14, Democrat Brian Nathan delivered a surprise upset over Republican Josie Tomkow.

Both races were close. Gregory won by just over two points while, as of this writing, Nathan leads Tomkow by just under half a percentage point, meaning it could head to a recount once all votes are counted.

But in 2024, races in these same districts weren’t close. There’s a big shift afoot nationwide—so big that even GOP candidates in ruby red Florida can’t take their seats for granted.

“MY COMPLETE AND TOTAL ENDORSEMENT”

Trump’s endorsement once carried significant weight, as the MAGA faithful came out in droves to support Dear Leader’s favored candidates. He tried to head off an upset in HD-87 by putting his finger on the scale in that race.

In a Truth Social post, which read differently than his cookie-cutter endorsements of other candidates, Trump gave Maples his “complete and total endorsement” and urged all “great patriots in the district to vote for Maples.”

He even brought Maples on stage with him at Mar-a-Lago:

But this time, it didn’t work. At least, not enough to stop the blue tide from sweeping in. A first-time candidate with a background in public health, Gregory defeated Maples by more than two points.

Blue accounts on social media celebrated the win, not just as a rare Florida flip, but as a personal loss for Trump. House District 87 encompasses Palm Beach and his home base of Mar-a-Lago. Trump will now be represented by a Democrat.

Emily Gregory’s win represents a stunning reversal. In 2024, Republican Mike Caruso won the district by 19 points. (Caruso resigned after Gov. Ron DeSantis appointed him clerk of the circuit court and comptroller of Palm Beach County.) Gregory swung the district 21 points toward Democrats.

Palm Beach was once staunchly Democratic, but in recent years Republicans have made significant inroads. Gregory’s win suggests that those may not have been permanent, especially with Republican enthusiasm down, Democrats fired up, and independent voters breaking toward Democrats.

In her first interview after winning, Gregory noted that while her opponent had put Trump at the forefront of his campaign, she focused instead on what ordinary voters need: lower property insurance, expanded healthcare and strong public schools.

March Madness-level upset

No one expected Brian Nathan, a union leader and veteran, to win his race for Senate District 14, which covers western Tampa and Hillsborough County. Republican voters outnumber Democrats in SD-14 by 22,000. And Nathan was outraised 10-1 by his Republican opponent, Rep. Josie Tomkow. Nathan also received little support from the state Democratic Party. Nikki Fried, who now leads that organization in Florida, even expressed surprise at the results.

She might be forgiven for this. Preliminary numbers had not predicted this flip. As Jacob Rubashkin of Inside Elections noted, the early vote seemed to favor Republican Tomkow heavily by some 3,000 ballots. But after 70 percent of the votes had been tabulated, Nathan was still leading! This led Rubashkin to a conclusion that should have the GOP sweating:

Republicans cast 3,035 more ballots tha[n] Democrats in the early vote for this race, but Democrats have a 3,069-vote lead. Back of envelope math (assuming most people vote their party) suggests the 9,493 unaffiliated ballots cast broke 2-1 Democratic.

We’ll need to unpack this after the smoke clears, but this result is consistent with a national pattern showing independents are deeply unhappy with Trump. In the latest poll by CBS/You Gov conducted March 17-20 on a survey size of 1,150 U.S. adults, Trump was 38 points underwater with independent voters. This is a little more than two to one disapproving—the same ratio Rubashkin noted in the SD-14 vote count.

In the end, Nathan came through, narrowly (unofficially) defeating Tomkow by just a few hundred votes.

Like Gregory, Nathan’s victory, if it is confirmed, represents a flip and a significant shift from 2024. In that election, the Republican won the race by seven points.

Florida adds to the GOP’s national woes

The Florida state Democratic Party has been in disarray for years. Nevertheless, in 2025 and now 2026, Democrats have racked up impressive performances. They handily beat expectations in special congressional elections and last year won the Miami mayorship for the first time in 30 years.

The twin victories by Democrats last night are giving ulcers to GOP incumbents and could strongly weigh against an attempted “dummymander” to try to eke out more congressional seats.

Nationally, the GOP is also rubbing its collective temples at the results. If candidates in the GOP’s big southeastern stronghold aren’t safe from an incoming Blue Tsunami, then they aren’t safe anywhere. Indeed, most of the legislative flips by Democrats have occurred in states controlled by the GOP, including Iowa, Arkansas, Mississippi, Texas, Georgia and now Florida.

Special elections aren’t necessarily indicative of what will happen in the midterms. And there’s a lot of time between now and November. But based on the track records of the parties on special state legislative elections over the past 16 months, I’d rather be us than them any day: The two wins yesterday in Florida bring the total seats flipped by Democrats since 2024 in special legislative elections to 30.

Republicans have flipped zero.