A long-held Republican state Senate district in a wealthy corner of Wisconsin could finally flip this fall when voters get to choose between a sitting Democratic Assembly representative and a political unknown.
State Rep. Robyn Vining, a Democrat who currently holds office in southeast Wisconsin’s 13th Assembly District, will square off against Republican Mike Roberts, a healthcare professional and business owner, in the Nov. 3 Senate District 5 race. Andrew Whitley, executive director of the Wisconsin State Senate Democratic Committee, says it should be an easy win for Democrats this year.
“It is the most flippable seat we have in the chamber,” Whitley said. “Kamala [Harris in 2024] won it by six points in what was theoretically not so great a year for Democrats, in a time when Trump won the state.”
Here’s how the race is shaping up in the wake of redistricting two years ago.
The district
Senate District 5 was redrawn in 2024, and this election will be the first time voters from the newly defined district choose a senator. The new boundaries have also made the district slightly more Democratic, Whitley said, a change that had been gradual even before the redrawing. And while the district has been under Republican control for about a decade, Democrats have come closer each election year to flipping the seat.
The district now includes the cities of Brookfield, Pewaukee, and Elm Grove, plus large portions of Wauwatosa and West Allis, as well as parts of Milwaukee and Waukesha. In general, it’s a district with relatively wealthy suburbs, which Democrats are working to earn back.
Sen. Rob Hutton (R-Brookfield) was first elected to the district in 2023. He was preceded by Republicans Dale Kooyenga and Leah Vukmir. But Hutton isn’t running for reelection this year, creating a set of circumstances that make it very likely Democrats can pull out a win.
“He read the tea leaves and got out of there,” Whitley said, citing hopes for a Democratic “blue wave” in the district that supported former Vice President Harris in the last presidential election. “I don’t know if he would have done that if his seat were two or three points bluer, but I think it has impacts on the type of Republican that wants to run—it makes it more likely that you’re going to see a Senator Vining this fall.”
Hutton is one of six Republicans choosing to leave the Senate instead of defending their seats, one-third of the GOP caucus.
The candidates
Republican Mike Roberts opened Wisconsin Orthopedic Physical Therapy in 2023 in Wauwatosa and Milwaukee. He’s married to a school teacher who also hails from Pewaukee. He’s never held office.
“He’s somewhat of an unknown with a big question mark,” Whitley said.
Roberts has said he wants to improve affordability for Wisconsinites, especially around healthcare access.
Earlier this year, Roberts’ business was sued by the state for failing to pay unemployment insurance taxes. The business has also sued a number of its own clients in small claims court.
UpNorthNews reached out to Roberts, but he did not return requests for comments.
Rep. Robyn Vining is a professional photographer in Wauwatosa who serves as the ranking member on the Assembly Committee on Mental Health and Substance Use Disorder Prevention. As a mom who lost her health insurance while pregnant and a small business owner, Vining has campaigned on a platform of fighting for families as if they’re her own.
And it’s worked so far. In 2018, back when Wisconsin’s maps were still some of the most gerrymandered in the country, Vining flipped her seat blue.
“We are in a strong position to win this race,” Vining’s team told UpNorthNews in an email. “From community organizing and volunteer recruitment to fundraising success, we have built the campaign that will win in November—but we will be taking nothing for granted and plan to give this race everything we have from now to November 3rd.”
Whitley said Vining’s campaign has knocked on thousands of doors to draw up support. She’s pushing for more affordable healthcare, childcare, housing, and utility rates, touting the overall affordability issue as one she’s long championed during her tenure in the Assembly.
The race
Because it appears promising for Democrats, many are viewing the race in the 5th Senate District as a litmus test for how the party will fare across the state on Nov. 3.
“Our early research shows it’s squarely in the lean Dem column,” Whitley said of the district.
Vining currently represents an Assembly district that closely aligns with the newly redrawn district maps—Whitley estimates that Vining has represented about two-thirds of the Senate district at some point during her time in office, given the changing maps.
Like most local races in the state and across the country, affordability remains a key issue for voters.
“No matter where they turn, they’re feeling the squeeze of rising prices,” Whitley said.
Because voters are increasingly looking to national politics to determine who to vote for at the state and local levels, Whitley sees the Trump administration’s handling of the affordability issue as a good way to gauge how voters will decide which party to vote for to address the problem locally.
“So much of our politics is less about actually what your school board or city council rep does; it’s more about who’s in the White House and what that national mood and feeling is,” Whitley said.
To that end, the Trump administration ran on a platform of prioritizing affordability for the average American, but has so far seen increased gas prices and inflation, which have made the problem worse, Whitley said.
“Last cycle we really had the wind in our face; we really feel it at our back this year,” he said.
