Winner and Loser of the Week in Florida politics — Week of 3.22.26

We’ve occasionally written recently about Democrats’ underdog position in upcoming election cycles in Florida as the state has turned more and more red the last few years.

As we wrote in our 2025 end-of-year column, “while Democrats hope to propel anti-Trump sentiment into a strong performance next November, it will take a massive blue wave to overcome Florida’s current Republican lean.”

… Is that massive blue wave coming?

The results from a few Special Elections this week for legislative seats has some Democrats hopeful, and some Republicans getting nervous, even if they won’t admit it publicly.

Now, Special Elections are special, and the electorate from this past Tuesday won’t be the same as the one in November. So we wouldn’t bet on a widespread upheaval across the state just yet.

But while Republicans are using that argument to project confidence in November, things could just as easily get worse for them come Election Day if news about the economy, war, and other hot-button issues continues going the way it is.

So Democrats certainly have the right to be more optimistic than they were a week ago. And to that end, let’s get to an election-centric edition of winners and losers.

Winners

Honorable mention: Hilary Holley, Samantha Scott. First, all is not lost for Republicans!

Yes, Democrats won the two highest-profile contests Tuesday (more, of course, on those later). But in House District 51, Republican Hilary Holley coasted to a win over Edwin Pérez to succeed Republican Rep. Josie Tomkow.

“Representative-Elect Hilary Holley in House District 51 will be a tremendous addition to the Florida House of Representatives, given her unmatched experience in the agricultural community,” House Speaker-Designate Sam Garrison said. “Voters have made the right decision in electing the far superior candidate.”

And in House District 52, Republican Samantha Scott avoided Tuesday’s chaos entirely, having locked up an uncontested bid late last year when no one else qualified for the Special Election here. Still, under Florida law, she had to wait until the scheduled General Election date Tuesday to officially be seated as the HD 52 Representative.

Scott will succeed former Republican Rep. John Temple, who is now the President of Lake-Sumter State College.

So yes, it’s not the biggest story of the night. But Republicans did hold these two GOP seats amid a scare induced by losing Republican-favored seats in Senate District 14 and House District 87.

Almost (but not quite) the biggest winner: David Jolly, Alex Vindman. And piggybacking off of those Democratic Special Election victories are the two current presumptive favorites to be Democratic nominees in the top two statewide contests this cycle.

Jolly is running for Governor, while Vindman is seeking to serve in the U.S. Senate. Both have to get through Democratic Primaries, and neither win is quite set in stone yet.

But as voters and donors evaluate the strengths and weaknesses of these Democratic candidates, both Jolly and Vindman have one strength in common: Both have the largest national name ID within their respective field. Jolly is recognized due to his longtime stint on MS NOW, while Vindman is known due to his status as a whistleblower who led in part to one of Donald Trump’s impeachments during his first term.

That puts both in touch with a broader potential donor network. It’s a nice perk, but it’s not necessarily an overwhelming edge in a cycle with limited resources in a state where Republicans have dominated the last two cycles.

Ah, but now that narrative is changing. Florida’s election results were national news. And that just gave Jolly and Vindman the ability to convince donors that Florida is more in play than not.

For out-of-state donors who are already on average more likely to see Florida as more purple than it really is, that message just instantly got more effective.

And come General Election time, no matter who is the Democratic nominee, their job just got easier in terms of rallying support for a potential upset.

The biggest winner: Brian Nathan, Emily Gregory. But as for the man and woman of the hour, it’s Nathan and Gregory, who secured those shocking wins in SD 14 and HD 87, respectively.

Republicans can call it a fluke. They can say these results aren’t replicable come November. Maybe they’ll be proven right here and elsewhere.

But the scoreboard matters above all else. Nathan and Gregory are now members of the Legislature with multiple vital Special Sessions on the horizon.

Nathan could, in the right environment, be a Senator from one of the most important districts in Florida into the next decade, although the swing nature of the district suggests he has his work cut out for him.

Gregory, because her district spans Mar-a-Lago, is one of the most important Democrats in Florida. She already earned a national news hit focusing on her most famous constituent. And while she brushed off Trump’s importance, the contrast isn’t going away anytime soon.

But most importantly, they’re now able to spend the next several months leading by action and making the case that voters should keep them right where they are for years to come.

Losers

Dishonorable mention: Trump. Trump’s appearance here is for two reasons.

First, the aforementioned indignity of being represented by a Democrat in his home district. That happened despite Trump World going all in to support the Republican candidate, Jon Maples. But Trump doesn’t even have the juice in his home district to keep Democrats out of power.

And that leads us to the second reason: These two races, added to Democrats’ success elsewhere around the country this cycle, are continuing to show an increasingly bad environment for Trump and Republicans.

Yes, it’s fairly standard for the party in power to lose steam in the Midterms. But there are more and more signs that the backlash against Trump 2.0 is going to be particularly strong.

And again, whether that spreads to Florida, where Republicans are winning by nearly 20 points in statewide contests in recent cycles, remains to be seen. But Florida can serve as a bellwether to the wider question of whether Trump can cut against the historical trends.

And the answer this week seemed to be a resounding no.

That’s due in part to the gravity of history, yes, but Trump’s own decisions aren’t helping. The antiwar candidate is potentially dragging us into the biggest conflict of many of our lifetimes. The business expert is overseeing an economy where prices did not fall, despite his promises, and are now either shooting through the roof (check the gas pump) or about to (check … all other goods that require gas to be shipped).

That’s not to mention an aggressive immigration policy that has turned off many middle-of-the-road voters who gave Trump a chance to dredge us out of a stagnant Joe Biden economy, a failure to be transparent about the Jeffrey Epstein files, or his character flaws that are too numerous to list.

It’s looking like a sad, low energy performance heading into November.

Almost (but not quite) the biggest loser: Jay Collins. Collins, of course, formerly represented SD 14 before Gov. Ron DeSantis tapped him to serve as his Lieutenant Governor.

That decision opened up the SD 14 seat, which Republicans have now lost. DeSantis also appointed former Republican Rep. Mike Caruso to serve as Palm Beach County Clerk and Comptroller, which opened up the HD 87 seat.

So, 0-for-2 there for the DeSantis administration.

But back to Collins, where was he? Because we certainly didn’t see him barnstorming through the district knocking on doors to help his party keep his old seat.

Collins claims that he wasn’t asked to campaign, but there are only two possibilities here and neither reflect well on Collins: either he wasn’t asked to campaign in his previous district which he won by 10 points, which says a lot about how irrelevant his influence is, or he was asked (which he was) and didn’t help.

So which is it?

The biggest loser: Wednesday morning quarterbacking. So right off the jump, we’re guilty of this as well (thanks for reading!). It’s hard not to look back and wonder what could have been done differently when confronted with an unexpected result.

But we have rarely seen this level of “Candidate X should have done this or that.”

Should Josie Tomkow have resigned from the House to run for SD 14 in the first place?

Should Senate leadership have leaned in more?

Should DeSantis have done this or that? (Again, we’re guilty of this too.)

Yet little to nothing was said aloud about any of this before the election results.

Inevitably, there will be some truth somewhere to some of these. Others will be overreactions based on what fits your priors.

But long-term, once the dust has settled and we have some distance here (plus more information come November), we may realize that micromanaging this or that decision was no match for larger trends at play: Floridians, and Americans, are unhappy with the current direction things are going. And they’re looking for a course correction.

If Republicans take too long to realize it, then voters will have nowhere else to turn but to the Democrats.