Republicans are bracing for what could be an embarrassing night on Tuesday, with elections set to be held in Wisconsin and Florida that are expected to see highly engaged Democrats turn out to register their dissatisfaction with President Trump only two months into his second term. 

Special elections are typically the best barometer of voters’ feelings early into a president’s term, with Senator Brown’s 2010 special election victory in Massachusetts and Senator Jones’s upset win in the 2017 Alabama race both being heralded as major wins for the then-opposition parties. It’s clear Republicans are starting to get nervous about their chances on Tuesday, given the fact that the White House withdrew the nomination of Congresswoman Elise Stefanik to be United Nations ambassador for fear that her deep-red district could flip blue in a special election later this year. 

In Wisconsin, Democrats and Republicans alike have invested heavily in the first major statewide race of Trump 2.0, which will decide control of the state’s supreme court. The campaign is expected to blow past previous spending records by the time polls close on Tuesday, with more than $100 million likely to be spent. 

Wisconsin’ highest court currently has a 4–3 liberal majority, though one of the liberal justice’s retirements has opened the door for the Republicans to take control. A former state attorney general and current county appellate judge, Brad Schimel, has won the endorsement of both Mr. Trump and Elon Musk, who is spending north of $10 million through his super PACs on the race to flip control of the court. The Democrats’ chosen candidate, Susan Crawford, is a county appellate judge from Madison. 

According to the latest poll from SoCal strategies, Judge Crawford leads Judge Schimel by eight points in a state that Mr. Trump won by just less than one point in November. 

Billionaires on the left and right have poured money into the state to try to sway the election. For the Republicans, Mr. Musk’s groups — America PAC and Building America’s Future — have spent nearly $15 million combined to support the conservative jurist. For the liberals, Governor Pritzker — heir to the Hyatt hotel fortune — and hedge fund billionaire George Soros each gave $1 million to the Wisconsin Democratic Party, which was then transferred to Judge Crawford’s campaign, according to the Brennan Center’s accounting. 

Members of the Wisconsin-based billionaire Uihlein family have also weighed into the race on both sides, with $4 million spent by outside groups backed by Richard Uihlein supporting Judge Schimel, and more than $6 million spent by an outside group funded by Lynde Uihlein to support Judge Crawford. 

The Wisconsin supreme court race is certainly a referendum on the president given how much he and Mr. Musk have been featured in ads from both sides of the aisle during the campaign, though ultimately, a win for Democrats in a state that Mr. Trump won with 49.6 percent of the vote is far from an upset victory. The biggest embarrassment for Republicans is likely to come from Florida on Tuesday, where the GOP is set to wildly underperform in a district that Mr. Trump won by more than 30 points only a few months ago. 

Special elections will be held on Tuesday in two U.S. House districts in Florida — one on the western edge of the Panhandle in a  district that was vacated by Congressman Matt Gaetz after he was nominated for attorney general, and the other on the east coast, south of Saint Augustine, which is now vacant due to the resignation of Michael Waltz who left the House to become national security advisor. 

The Republican candidate for Mr. Gaetz’s seat, Jimmy Patronis, currently serves as Florida’s chief financial officer, and is widely expected to win the seat comfortably. For Mr. Waltz’s 6th district, however, the Republican candidate is at risk of wildly underperforming past GOP candidates. 

The Republican candidate, State senator Randy Fine, is already far behind in terms of campaign funds. The Democratic candidate, Josh Weil, has raised nearly $9.5 million for his campaign in just one month, while Mr. Fine has raised a meager $987,000. 

The newest survey in the race from St. Pete polls show Mr. Fine leading Mr. Weil by only four points, 48 percent to 44 percent, with the poll’s margin of error being five points. In November, both Messrs. Trump and Waltz won Florida’s 6th district by more than 30 points. 

Governor DeSantis — who represented the 6th district in the House for three terms — is trying to temper expectations about the special election results on Tuesday. He and Mr. Fine have famously been sparring for years, since Mr. Fine refused to endorse his own governor in 2024 GOP presidential primaries, and the governor now says that the guaranteed underperformance by the Republican nominee on Tuesday is a reflection not of the president or the party writ large, but rather of Mr. Fine himself. 

“I will tell you this: regardless of the outcome in that, it’s gonna be a way underperformance from what I won that district by in ‘22 and what the president won it by in November. They’re gonna try to lay that at the feet of President Trump. That is not a reflection of President Trump. It’s a reflection of the specific candidate running in that race, and President Trump, if he were on the ballot in the special election, he would win by 30 points,” Mr. DeSantis said of Mr. Fine at a press conference on Tuesday. 

“The liberal media in Washington … they’re gonna try to weaponize that against the president,” if Mr. Fine loses or wildly underperforms, the governor added. “As somebody that’s been around the block here in Florida on this stuff, I can tell you that’s not [the case]. It’s a candidate-specific issue.”