State Superintendent Underly Seeks Reelection, Faces Challenger

Department of Public Instruction Superintendent Jill Underly, who is running for her second term in office with the backing of the Democratic Party of Wisconsin, faces a challenge from Sauk Prairie School District Superintendent Jeff Wright, a Democrat who says he wants to improve DPI’s communication.

Elections for the state superintendent are technically nonpartisan. Candidates run on the same ballot in the February primary, and the top two advance. The primary is Feb. 18, 2025 and the general election is April 1. No other candidates have entered the race so far.

Underly won her first term in a landslide in 2021, defeating her conservative opponent, a retired superintendent backed by Republican-leaning groups, in a campaign cycle where a record $3 million was spent on the race by candidates and outside special interest groups.

In her September campaign announcement, Underly highlighted some of her accomplishments, and said that students and staff need to be supported in Wisconsin.

At the helm of the agency, Underly has advocated for increased investments in public education in the state budget, including for special education funding, mental health resources, staff pay and more. She recently announced a budget request that would dedicate an additional $4 billion in state funds to  public education. The DPI under her leadership also helped shape a law that reforms the way reading is taught in Wisconsin schools, though the Legislature has not released the money to support the changes despite Underly’s multiple urgings.

Underly also highlighted the ongoing politicization of schools in her statement. Throughout her tenure culture war issues have continued to divide voters at the state and local level and she has been an outspoken critic of efforts to cut diversity, equity and inclusion programs and to target LGBTQ+ staff and students.

“I’ve fought for kids and their teachers to be their true selves in school and stood up to ensure they see themselves represented in their curriculum and in their libraries,” Underly said in a September statement announcing her reelection campaign. “In a second term as superintendent, I want to make sure we continue to make necessary investments in our kids, as well as continue to examine how we evolve education to meet the challenges of the future.”

Prior to winning her first term in 2021, Underly served as the superintendent of Pecatonica School District, a rural district in southwestern Wisconsin. She has also previously worked as a principal, a teacher and a state consultant to Title I schools in Milwaukee and across the state.

Wright, who launched his campaign about a month after Underly, has served as the superintendent of Sauk Prairie School District since 2019 and was named Administrator of the Year in 2024 by the Wisconsin Rural Schools Alliance. He also previously served as a principal in Chicago. He hasn’t held public office before, but has run unsuccessful campaigns in 2016 and in 2018 for the state Assembly.

Wright said in an October interview with the Examiner that he probably aligns closely with the current superintendent on many issues, but he thinks there is currently a “disconnect” between DPI and schools.

“They’re not bringing the people together from the teachers’ union, the administrators’ associations and other groups to have an active conversation about what concrete steps are we taking right now to get this work done,” Wright said. “Schools want to know what’s happening at the DPI. We don’t want to be surprised by changes. We want to be in conversation so that it’s very clear that we’re working on the same team.”

Wright cited concerns about whether enough effort has gone into recruiting and retaining educators. He said that he’s also heard “palpable frustration” from educators about the change to standardized testing scores and the lack of communication with school districts about it. The agency lowered the proficiency threshold and changed the terms that are used to to describe student performance, which critics said made it difficult to make comparisons to previous years.

Wright said that he would set himself apart from the current administration by trying to minimize partisanship. He said his district has tried to do this “by making sure that we’re listening to everyone and that we make sure that our doors aren’t closed to people, regardless of their opinion, especially if their children are in our schools.” He said that he hopes “it would also allow for more open conversations with legislators of all political stripes.”

Wright noted that DPI wasn’t invited to testify to the JFC during the last budget cycle.

“That hurts the DPI. It also hurts public education when we’re not having that open conversation between the agency charged with leading public schools and standing up for them and the legislators who are creating the budgets that do need to be rewritten,” Wright said. Underly did address lawmakers in person at one of the public hearings held by the committee in Eau Claire, but DPI was not invited to make its budget presentation to the Joint Finance Committee during the last budget process.

Wright said schools are also facing challenges as the current funding formula, including for special education, has made it difficult for schools to keep up with costs. He said that funding going to voucher schools “worries” him as well because “there aren’t enough resources for public schools at this point.”

Early supporters of Underly and Wright

Wright has said he was encouraged to run by educators and education professional associations. He did enter the race with a notable supporter — the Wisconsin Education Association Council (WEAC) Political Action Committee.

The Wisconsin Education Association Council is the largest teacher’s union in the state, and its PAC, which aims to help elect “pro-public education” candidates to office, recommended Wright in the race. However, the endorsement process for the full union is ongoing, and it’s unclear when or if a full endorsement will come from the board.

WEAC spokesperson Christina Brey said the PAC’s recommendation is one part of the lengthy endorsement process and said she couldn’t comment on specifics.

“WEAC is in the process of exploring the candidates for state superintendent, and its political action committee has recommended its support of Jeff Wright; however, the process is still ongoing, with no determined timeline on whether or if a decision will be reached,” Brey said.

When asked about the specifics on why the PAC recommended Wright, Brey said she couldn’t comment. She also said she couldn’t speak to the relationship between Underly and the union over the last four years due to the ongoing endorsement process.

Brey told the Examiner that when it comes to the superintendent race, Wisconsin educators are looking for strong and bold leadership and someone that cares as much about students as teachers do. She said some of the issues at play include figuring out how to keep teachers and support staff, how to address the workplace environment, how to handle challenging student behaviors and how to address school funding challenges. She said members will be looking at many things, including policies that have been enacted over the past few years, how those policies have “shaken out” in the classroom, where candidates fall on those issues and who they think will be the best listener, advocate and partner.

Other Wright supporters, according to campaign manager Tyler Smith, include Jim Lynch, Executive Director of the Association of Wisconsin School Administrators. Lynch told the Examiner in an email that the association’s process for endorsing candidates for state superintendent doesn’t begin until later this month, so he couldn’t speak for himself or the association until after the process.

Smith also named the superintendents of Mauston, Reedsburg, Stevens Point and Poynette school districts and the principals of Sauk Prairie High school and Sun Prairie School Board president as supporters.

Meanwhile, the Wisconsin Democratic Party endorsed Underly for a second term at the end of November. Party Chair Ben Wikler called her a “steadfast advocate” for students, parents and schools in a statement.

“From fighting to give rural school districts a seat at the table, to expanding mental health services in schools, to ensuring every school, teacher, and student has the resources they need to succeed, Dr. Underly is the proven leader we need championing our kids in the Department of Public Instruction,” Wikler said.

“At every step, Dr. Underly has had the backs of our kids, standing up to attacks on public education, libraries and LGBTQ+ youth, and ensuring that partisan attempts to divide Wisconsin do not undermine our state’s fundamental and uniting commitment to great public schools, available to all,” Wikler continued.

The state party’s endorsement prompted a strong response from Wright, who said it represented party “insiders” deciding to “ignore” the voices of teachers, administrators and other stakeholders and settling “for the division and mismanagement that have marked Superintendent Underly’s tenure, ignoring failures that are isolating DPI from discussions about the future of Wisconsin’s public schools.”

“Party leaders even ignored the voices of organized educators, a key member of the Democratic coalition, in making this endorsement,” Wright said.

The endorsement process for the state party was launched by two county parties — Waukesha and Milwaukee. Waukesha County Democratic Party Chair Matt Mareno said in a statement to the Examiner that the party was proud to put Underly’s name forward for the endorsement.

“We stood with her when she first ran, and in the years since she’s stood with us shoulder-to-shoulder as we’ve faced down far-right attacks on our public schools,” Mareno said. Schools in Waukesha County have dealt with a number of issues in recent years including becoming the target of a bomb threat and a threatened  school shooting after a right-wing social media account publicized  posts made by a local middle school principal, as well as books and songs being banned from schools.

“From book bans to bomb threats inspired by right-wing influencers, our community and schools have been through a lot,” Mareno said, “and Jill Underly has been there with us at every step fighting for a better future for our kids.”

State superintendent race kicks off: Underly faces challenge from Sauk Prairie superintendent was originally published by Wisconsin Examiner.