What to Watch For in Tuesday’s Wisconsin and Florida Special Elections

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During a closed–door meeting last week, House Majority Leader Steve Scalise gave his fellow Republicans an ice-cold dose of reality: Tuesday’s special elections in Florida, and maybe even the super-pricey Supreme Court race in Wisconsin, were poised to be bad for the GOP brand.

In a Florida House district that went Republican by 30 points in November, the Democrat is polling just a few points behind and out-raising his rival by a 10-to-1 margin. In the other House race in that state, a 40-point GOP advantage is registering at about half that rate in early vote numbers. Meanwhile, the Wisconsin race, where Elon Musk is handing out $1 million checks, is a true jump ball.

That’s why Scalise was meeting privately with Republicans last Tuesday to issue this warning: even in a GOP sweep, the election results are going to raise inevitable questions about the fragile GOP standing and the fading power of Trump’s endorsement. Scalise—like leadership-aligned Democrats, speaking candidly—expects the Florida seats to stay red, but the slide is going to be tough to ignore.

Here are the players and stakes for all three races.

Florida’s 6th District: Randy Fine vs. Josh Weil

Back in November, Republican Mike Waltz won re-election in Florida’s Sixth district by 33 points. When he resigned to become Trump’s National Security Adviser, the assumption was the seat was still a safe Republican hold. 

But a March private poll from a firm close to the Trump White House showed Republican state Sen. Randy Fine ahead by just 3 points, according to Hill aides who have dug into the crosstabs. That was much closer than the 12-point spread in February. It’s a clear sign that the Democrat, Orlando teacher Josh Weil, has effectively tapped into national frustrations with the second Trump term.

Florida Gov. Ron DeSantis has been sniping his fellow Republican in recent weeks for running a campaign as though Fine had already won. Trump this past weekend held an eleventh-hour telephone rally to remind his MAGA faithful of his preference, and Musk is rushing in with tens of thousands in new ads. GOP leaders in Washington are well aware that Fine was incredibly late to get his own first ads on airwaves.

“I would have preferred if our candidate had raised money at a faster rate and gotten on TV quicker,” Rep. Richard Hudson of North Carolina, House Republicans’ campaign chief, told reporters last week. “But he’s doing what he needs to do. He’s on TV now.”

The seat should have been a safe Republican hold—and probably still is, if folks are being honest—but the fact that Democrats are running up the score here is going to raise more grumbling about Trump’s gut-based endorsements, and whether this race is a sign of a bigger problem for the party nationally.

Florida’s 1st District: Jimmy Patronis vs. Gay Valimont

Before he resigned from his House seat in hopes of becoming Trump’s attorney general, Republican Matt Gaetz won re-election in Florida’s First by 32 points. Most strategists describe the First District, which covers the western Panhandle, as the most Republican in the state—a place where Democrats have little hope of tipping the race blue.

Yet some Democratic donors are clearly buying the hype that an enormous Trump backlash is in the offing. Gay Valimont, a gun-safety activist who is running for the seat again after getting creamed by Gaetz last year, hauled in more than $6 million through mid-March—a lapping of Republican Jimmy Patronis, by a factor of five.

Just as Weil has tried to nationalize his race—wins in both districts could potentially turn the House blue and give Hakeem Jeffries the title of Speaker—Valimont is trying to make her contest as a referendum on checking Trump’s power. Where Weil is still making the race about his opponent, Valimont is very much running directly against Trump and racing right past Patronis, the state’s CFO. Still, both Democrats are hoping to ride the national mood on opposite sides of the state.

Democratic donor-advisers have taken the pair of races as symptoms of what happens when activists are taken in with races that carry plenty of symbolism but no viable path to victory. But here is the surest signal that these races are not priorities for anyone with real power in the Democratic Party: House Democrats’ official campaign arm is not playing in either race in Florida. While some, like Jeffries, have cut checks as signs of support, the major spigot of cash has remained closed. 

Wisconsin Supreme Court seat: Susan Crawford vs. Brad Schimel

State judicial races rarely draw big spending. Yet some estimate the money to decide who gets a single seat on Wisconsin’s highest court will top $100 million, with $20 million alone coming from Musk. To put that in perspective, the average cost per winning U.S. House campaign in the last midterm elections was roughly $2.8 million. 

Wisconsin has emerged this century as the most unlikely of high court battlegrounds. The state’s politics, perhaps as much as any of its neighbors, has had a massive reset of alignment. What was once a safe GOP harbor for the likes of former Gov. Scott Walker gave way for a rising union machine, but it still allowed GOP Sen. Ron Johnson to win re-election over one of the 2022 cycle’s rockstar candidates, Mandela Barnes.

Put simply: a bet on Wisconsin’s political DNA in the coming years is a gamble that only fools would take.

That’s why, just Sunday night, Musk was on Wisconsin stage tossing an autographed cheesehead hat into the crowd. The race is rocketing to new levels of spending, putting it on par with marquee Senate races and surpassing what even some presidential bids collect. The stakes include workers’ rights, voting rights, and abortion rights as the winner will decide which team prevails on a 4-3 state Supreme Court. The plum political prize, of course, will be deciding how congressional districts are drawn, perhaps giving this parochial court a major say in which party—and its preferred Speaker—gets to run the U.S. House.

Madison politics has been drawing outsized attention for more than a decade now, starting with a string of union-testing efforts and a recall-palooza that set back a progressive march. The national glare, to those working there, is getting old.

More recently, Democratic Gov. Tony Evers and a Republican legislature have been riding a tense tightrope of governing frailty. The courts have been hanging back, awaiting the results of Tuesday’s balloting. 

There’s no party ID on the ballots, but it’s clear the party affiliation of the two candidates as they each chase a promotion and a 10-year term. Brad Schimel, a former state Attorney General and currently a Waukesha County judge, is carrying an endorsement from Trump. Dane County Judge Susan Crawford snagged the support of former President Barack Obama. 

And both candidates have their share of billionaire buddies in their back pockets. Think of the typical boogeymen: George Soros, Dick Uihlein, Musk. Even actor Kevin Bacon has found his way into this tangle of out-of-state donors. But it’s Musk who is topping the ranks and making the race all the more divisive with his visit that passed out $1 million checks like candy and his other efforts to use his money to encourage rank-and-file voters to cast ballots. In a twist, the legality of those moves have made their way to the court currently in play.

Tuesday’s election in Wisconsin is the lone statewide contest before voters this year, making it a tempting test case for political nerds. By all accounts, the whole Democratic playbook is making the election a referendum on Musk, the biggest cash source in the race. But it’s also a warning; if the courts are so transparently for sale, can they actually be trusted to be neutral umpires for what’s right and wrong?

State Legislative Races Trending Blue

All three of these races are coming on the heels of a few legislative races with results that may hint at a larger Trump backlash, or may just be a lot of noise. Observers are prone to over-interpret the results of special elections, to be sure. Often, we’re looking at just thousands of votes cast, when most voters are unaware there is even an election happening. But they can be useful in diagnosing a mood. For instance, after the Supreme Court ended the federal right to abortion with the Dobbs decision, the backlash in special elections was immediate and Democrats cruised to a strong showing in the 2022 midterms.