Democrats have largely given up the hope of notching a major win in Florida anytime soon as the state solidifies its deep-red status, but according to one conservative writing for The Hill, one of President Donald Trump's many enemies has a legitimate shot at winning a seat in the Sunshine State.

Myra Adams is a regular contributor for The Hill who previously worked on the creative teams for Republican presidential campaigns in 2004 and 2008. In her latest piece from Friday, she advised that people should "expect the unexpected" when it comes to the results in the fast-approaching November midterms, and that includes a potential Democratic upset in Florida, the newest GOP stronghold state.

"Nationally, President Trump’s gloomy average job approval rating of 39 percent is linked to rising gas prices," Adams wrote. "Meanwhile, in his adopted home state of Florida, his approval is 43 percent, yet 70 percent of Floridians say they are 'falling behind' the cost of living. These figures do not bode well for an easy Senate race, which is currently ranked 'solid Republican' but likely to tighten."

She added: "In November 2024, Trump won Florida by a 13-point margin. Now, the appointed incumbent, Sen. Ashley Moody (R-Fla.), must appease the state’s irate electorate. Moody served as Florida’s attorney general until Republican Gov. Ron DeSantis (R) tapped her in January 2025 to fill the Senate seat vacated by Marco Rubio when named Secretary of State."

While Moody remains tipped to retain her seat for the time being, she is facing considerable competition from the leading candidate for the Democratic nomination: Alexander Vindman, a retired Army lieutenant colonel who boasts a contentious history with Trump. In 2019, Vindman was one of the key whistleblowers who testified against Trump for the phone call with Ukrainian President Volodymyr Zelensky that ultimately led to his first impeachment.

Despite the red-state headwinds, Vindman has built up major momentum in the race, with "optimistic" internal polling numbers and nearly the same fundraising haul as Moody.

"The Vindman versus Moody race pits a Trump 'yes-woman' placeholder against an enemy of the president. Vindman suffered for what he believed was his patriotic duty," Adams wrote. "Vindman’s unique story could resonate with voters as Trump slides toward authoritarian rule, unleashing the Justice Department to reward his allies and punish his enemies. Florida is a red state, but Democrats have recently prevailed in several local races. local races."

Vindman is also not shying away from taking his message straight to GOP voters, vital in a state where the party has a major lead in voter registration. Adams noted how impressed she was to see him campaigning in The Villages, an epicenter for Florida's older, retired and white Republican voters. Those sorts of connections, she argued, "sound the MAGA alarms."

“When I say we are not just going to blue districts, but ruby red, too, I mean it," Vindman said. "It’s why I was in The Villages earlier this month, walking the line of people waiting to attend a Trump rally, connecting with registered Republicans who are also fed up with rising costs, corruption in D.C., and foolish wars of choice that are not just putting our service members’ lives at risk, but causing costs to skyrocket for families who are already struggling to get by.”

President Donald Trump's wife and youngest son have now also been caught voting by mail in Florida despite the president's ongoing campaign to ban vote-by-mail, the Daily Beast reported.

“Mail-in voting means mail-in cheating. I call it mail-in cheating, and we've got to do something about it all,” Trump said on Monday while participating in his crime task force roundtable.

It was after Trump and his family submitted their mail-in ballots, records show.

There was a special election in Florida's House District 87 on Tuesday, where a Democrat won in a huge upset. Trump previously won the district with 11 points above Vice President Kamala Harris. Winner Emily Gregory scored two points above Trump's 2024 percentage.

Her new district covers Trump's Mar-a-Lago country club. Trump had endorsed the Republican, and he significantly outspent Gregory, CBS12 reported.

Trump has been pushing the SAVE Act, a measure that would "prohibit universal mail voting, requiring all mail voters to submit an application in order to receive a mail ballot. This would end the longstanding principal method of voting in eight states and Washington, DC," the Brennan Center explained.

Trump's voting bill would also require Americans to bring some kind of proof of citizenship to register to vote. As it stands, most Americans can use their driver's license when registering to vote. But 45 states, 16 territories, and Washington, D.C. don't indicate citizenship on the driver's license. So, Americans would be required to bring either a passport or a birth certificate along with their driver's license to register to vote.

It's unknown whether every American would be required to re-register to vote.

NPR news reported that Trump has cast mail-in ballots throughout his time in the White House, dating back to 2020.

In August, Trump wrote on Truth Social he would “lead a movement to get rid of MAIL-IN BALLOTS,” claiming the U.S. was “the only Country in the World that uses Mail-In Voting” and that “ELECTIONS CAN NEVER BE HONEST WITH MAIL IN BALLOTS/VOTING.”

Many polls released in March showed the Democratic Party struggling badly from an approval standpoint. The number of U.S. voters who held a "favorable" view of the Democratic Party in March ranged from 31 percent (Quinnipiac) to 39 percent (YouGov) to 37 percent (Yahoo News). And yet, Democratic candidates have been enjoying a series of victories in special elections in 2026 — even in some red states.

Two of those victories came on Tuesday, March 24, when Democrats Emily Gregory and Brian Nathan won Florida State Legislature races in GOP-friendly districts. Gregory won in the district where President Donald Trump's Mar-a-Lago resort is located.

MS NOW's Ryan Teague Beckwith, in an April 1 opinion column, stresses that these victories don't mean the Democratic Party is growing in popularity but rather, indicate that many conservative voters are so frustrated that they are staying home on Election Day.

"Last Tuesday," Beckwith explains, "the Democratic candidate won the state legislative district that includes Trump's Palm Beach estate, Mar-a-Lago; beat a Republican candidate whom Trump had just wholeheartedly endorsed, flipping the district from GOP control; and had a 2-point winning margin in a district Trump won by 17 points in 2024. After her win, Gregory told MS NOW that she was 'pretty shocked' and 'having a fairly out-of-body experience'…. Even apart from the election's unusually direct tie to Trump, though, there's a reason why special elections like Gregory's — and another in Florida that flipped a state Senate seat Monday — get such outsize attention."

Beckwith continues, "Research shows they really are predictive of what may happen in the midterm elections, but not for the reason you may think."

Gregory's victory over Trump-backed Republican Jon Maples, Beckwith argues, reflects GOP voters in Florida sitting out the election — not Republicans taking a liking to Democrats.

"Since the 2024 election," the MS NOW columnist writes, "Democrats have flipped 30 seats that were held by Republicans everywhere from New Hampshire to Texas, including a state Senate seat in Florida declared on Monday, according to a tally by The New York Times. For their part, Republicans have not flipped any Democratic seats. That's a bad sign for Republicans running in November, but not because their supporters have changed their mind about voting for them. It's because their supporters have changed their mind about voting at all."

Once known as an unpredictable swing state that former President Barack Obama carried in both 2008 and 2012, Florida has turned increasingly Republican in recent years and become a major source of frustration for Democrats. Gov. Ron DeSantis ran a far-right campaign and was reelected by roughly 19 percent in the 2022 midterms; then, in 2024, Donald Trump defeated Democratic presidential nominee Kamala Harris in Florida by roughly 13 percent.

Republicans have been seriously dominating Florida politics. But on Tuesday night, March 24, two Democrats prevailed in special elections for Florida House of Representatives seats in GOP-friendly districts: Brian Nathan in the Tampa area, Emily Gregory in Mar-a-Lago's own district. Gregory only won by 2 percent, but she did so in a district that Trump won by double digits in 2024.

In an article published by The Bulwark on March 25, Never Trump conservative Bill Kristol emphasizes that the importance of Nathan and Gregory's victories goes way beyond Florida — as they are symptomatic of a broader "rebuke" of Trump's policies.

"To add a well-deserved insult to the electoral injury," Kristol argues, "House District 87 includes Mar-a-Lago. It's Trump’s home district…. In any case, Tuesday's secret ballots in Florida were a rebuke to Donald Trump. And at the national level, a Reuters/Ipsos poll completed Monday had Trump's approval rating at 36 percent — down 4 points in the past week — with 62 percent of Americans disapproving. This was Trump's worst showing in this poll since he returned to the White House."

Kristol continues, "Are things going to get better soon for Trump? It seems doubtful."

The Never Trumper predicts that the war with Iran will only add to Trump's unpopularity if it expands.

"Trump’s war is unpopular," Kristol writes. "The same Reuters/Ipsos poll showed 35 percent approval and 61 percent disapproval of the strikes against Iran…. Meanwhile, Democrats forced another vote in the Senate yesterday to require congressional approval of Trump's war. Republicans defeated the measure. So we now have a major war, well into its fourth week, which Trump is threatening to expand to a ground war — all being done without congressional approval, and all the sole responsibility of Donald Trump and his Republican Party."

Though it's unclear if Florida can once again become a swing state, Republicans have "a lot of nervousness," while Democrats are feeling newly energized after the results of another election in President Donald Trump's own backyard, per a new report from The Hill.

On Tuesday, Democrat Emily Gregory won a state legislative district in Florida, besting the Trump-endorsed Republican Jon Maples and flipping the seat in the process. The Democratic Party had put considerable effort into the race, given that the district encompasses the part of Palm Beach County where Trump's Mar-a-Lago is located. While the area is more politically purple than many parts of Florida, it was still a district previously held by a Republican, and which Trump won handily in 2024.

This race represents the latest in a growing string of elections wherein Democrats have pulled off major victories or come much closer to winning than anyone could have anticipated. Party leaders say this trend is a sign that voters are fed up with Trump's leadership and the GOP overall, and that the midterms will see serious gains in the upcoming midterms.

Gregory's win has also given Democrats a much-needed dose of optimism about the future chances to be competitive in Florida again. While it was once viewed as a swing state, ever since 2016, Florida's major statewide election results have consistently favored Republicans. Speaking with The Hill Friday, some in the party stressed that the state is not becoming purple again anytime soon, but the latest Democratic win has emphasized their "nervousness."

“There’s a lot of nervousness among Republicans with the fact that he’s so underwater with only seven months to go for the midterms because they’re on the ballot,” an anonymous former Trump campaign adviser told the outlet. “He’s not.”

They added: “There’s no real chance of losing the state, let’s say at the governor level. Florida is such a red state right now, has gone that way in the last 10 years that it’s hard to see Florida… even turning purple again.”

Despite that prediction, the former adviser admitted that Gregory's win was "a sign of unpopularity" for Trump and the GOP.

Fernand Amandi is a Democratic strategist currently working on the Florida gubernatorial campaign of David Jolly, a former Republican congressman now running as a Democrat. He told The Hill that Gregory's win left some "indisputable" takeaways.

"The reason is that we are now seeing in Florida what is happening everywhere else across the country, which is a double-digit Democratic over-performance in every single election since Donald Trump has retaken the presidency," Amandi said. "It doesn’t mean that Florida is now a purple state or a blue state, but it does mean for the first time, I think since 2018, you can start to now say that Florida is back in play."

With the 2026 midterms a little over seven months away, Democratic strategists are feeling cautiously optimistic. Democratic candidates have enjoyed a series of special-election victories in 2026, including some in GOP-leaning districts — and President Donald Trump continues to suffer from weak approval ratings in poll after poll.

In an op-ed published by The Hill on April 1, Democratic strategist Brad Bannon argues that the worse GOP infighting becomes between now and November, the better it will be for his party.

"Two dramatic and traumatic events in recent days illustrate the fragility of the unholy coalition which brought Donald Trump to power only ten years ago," Bannon explains. "These divisions increase the odds for a big Democratic win this November. The first mega MAGA meltdown occurred at the annual confab of the Conservative Political Action Committee. The group's chair, Matt Schlapp tried to warn the crowd that a Democratic midterm takeover of the House of Representatives would lead to Trump's impeachment. Failing to read the room, he asked the right-wing faithful if they favored their Dear Leader's removal. The crowd reacted with cheers and applause. Schlapp responded that was the 'wrong answer.'"

Bannon continues, "It certainly wasn't the response he expected…. Then, things got really ugly with a sharp split between House and Senate Republicans just before the congressional holiday recess. The Republican congressional majority left our nation's capital without passing a new budget for the immigration enforcement agencies."

Bannon argues that while Democrats are "singing in harmony," Republicans "sound discordant notes."

"There also exists a sharp split between Republican identifiers and MAGA supporters," Bannon observes. "One out of every five rank-and-file Republicans disapprove of Trump's performance, but only one in ten MAGAs give him a bad grade. Midterm elections loom like the Sword of Damocles over the right-wing extremists that call Trump 'daddy.'"

Bannon adds, "April showers bring May flowers, and Republican divisions in the spring bring Democratic additions for the fall."

Although the Democratic Party is suffering from low approval ratings, many of their candidates have been performing well in a series of special elections in 2026 — including two for seats in the Florida House of Representatives on Tuesday, March 24. Florida has grown increasingly Republican in recent years, yet in those races, Democrats were victorious in two districts known for being very favorable to President Donald Trump.

Brian Nathan won in the Tampa area, while fellow Democrat Emily Gregory prevailed in the Palm Beach-area district where Mar-a-Lago is located. Similarly, Democrat Taylor Rehmet enjoyed a double-digit victory in a Texas State Senate special election in February, which was a shocker considering that Trump won that district in the conservative Fort Worth suburbs by 17 percent in 2024.

Some political analysts believe that Democrats' recent winning streak doesn't mean that their party is popular, only that Trump is so unpopular.

In his March 27 column for the Washington Post, Never Trump conservative George Will argues that Democrats have an advantage going into the 2026 midterms. But he warns that they could blow it.

"Sen. Daniel Patrick Moynihan, a liberal with a conservative disposition — he thought conservatism is a disposition — once said, 'Liberals are people who would like to see things improved, and conservatives are people who would like to see things not worsened,'" Will writes. "Today, many voters at both ends of the ideological spectrum primarily want the same thing: to see the other side lose…. The Democrats' gains are largely from former Republicans switching parties out of disgust with Trump. The Republicans' gains include many former blue-collar Democrats, but 'more disaffected nonvoters coming out of political inactivity to vote for a once-in-a-lifetime candidate.'"

Despite all that "disgust with Trump," Will argues, Democrats could blow the midterms.

"Now, never underestimate the Democrats' ability to make a sow's ear out of a silk purse," Will writes. "As an Israeli diplomat once said of the Palestinians, they never miss an opportunity to miss an opportunity. If many Democratic candidates try to pump up deflated hysterias — democracy is dying, the planet is frying — they can make themselves resemble a, to recycle a phrase, basket of deplorables. Failure is a choice."

Democrats are once again making a major push to flip a state-level office in a special election, this time in Donald Trump's own backyard.

Per a Friday report from Politico, a special election will be held on March 24 in the Florida state house district that contains the part of Palm Beach where Trump's Mar-a-Lago resort is located, after its previous GOP representative was elevated to Palm Beach County clerk and comptroller by Gov. Ron DeSantis. The previous officeholder won reelection in the district by 19 points, while Trump carried it by 9 points in 2024. Despite those recent numbers, Politico noted that Palm Beach leans Democratic overall, setting the stage for a major upset.

Florida Democratic Party Chair Nikki Fried said that the party is backing nominee Emily Gregory "with everything we’ve got," making the race a top priority to "flip the president’s home district" and send a major symbolic message ahead of the midterms. Aside from the message to Trump, such a win, Politico explained, would also help embolden the state's "beleaguered" branch of the Democratic Party and set them up to break the GOP's supermajority in the Florida legislature in November. It would also help grow the nationwide party's midterm momentum as another in a growing trend of electoral wins amid Trump's cratering popularity.

Trump has endorsed the Republican in the race, former Lake Clarke Shores council member and financial planner Jon Maples. Despite that, neither he nor his opponent has made the president a central figure of their campaign, opting instead for an affordability message that has resonated with voters in numerous races over the past year.

“Since the Republicans gained a supermajority four years ago, we have not seen any of the affordability crisis issues, any of the housing — anything that would bring real relief to Florida families,” Gregory told Politico. “And it feels like every session is more targeted on harming Florida families and vulnerable populations.”

“In those big moments, athletes have to rise to that occasion,” Maples said of his candidacy. “And when you get the endorsement of the president, it’s a call to rise to the occasion.”

Despite Florida's noted shift to the right in the last few decades, there have been some big signs that Democrats might be able to notch significant gains in the state. In December, Eileen Higgins staged a massive electoral upset, becoming Miami's first Democratic mayor since 1997, besting the Trump-backed Republican candidate by 18 points.