Kaleem Caire, the longtime education and equity leader and founder of One City Schools, says Madison needs a clearer vision for its finances, economic growth and early literacy — and a bridge builder to carry it out.
Caire, a lifelong Madisonian, officially kicked off his campaign for mayor at the Center for Black Excellence and Culture on Monday afternoon.
“Madison needs a bridge builder right now,” Caire tells Madison365. “They need a catalyst and a leader but also somebody who can run a business and make difficult, tough decisions while also focusing on the things that matter.”
He says he is running for mayor because the city that raised him still has not lived up to the promise it made to children like him.
“As a kid, what you’re told is: If you work hard and do everything right, you can thrive here,” Caire tells Madison365. “The reality is, too many people still can’t afford to stay in the city they grew up in.”
Caire grew up on Madison’s South Side, down the street from Penn Park, and attended Franklin Elementary, St. James, Cherokee Middle and West High schools. He is a graduate of the University of Wisconsin-Madison.
Caire has spent much of his career working to address racial and economic disparities. He returned to Madison in 2010 to become president and CEO of the Urban League of Greater Madison after spending about a decade working in education reform and related organizations on the East Coast, primarily in Washington, D.C.
According to his bio, Caire has held executive leadership positions with Target Corporation, Fight For Children of Washington, DC, Black Alliance for Educational Options (BAEO), American Education Reform Council, Wisconsin Center for Academically Talented Youth (WCATY) and the Wisconsin Department of Public Instruction.
In 2014, he founded One City Schools, an early-learning and K-12 education initiative on Madison’s South Side that has focused on addressing racial disparities in educational outcomes.
A return to Madison
Caire says he was recruited back to Madison by LaMarr Billups, the late prominent Black civic leader who wanted to develop a new generation of Black leaders in the city.
Caire recalled that Billups, a longtime UW–Madison community relations leader and former senior assistant to the university’s chancellors, initially encouraged him to take the job at the Urban League and eventually told him he wanted Caire to run for mayor.
“When I came to Madison, I set about creating an ecosystem here by leveraging the Urban League of Greater Madison to build visibility around our people and also position other leaders and talented individuals for opportunities,” Caire says.
“I wanted to identify that talent, position people well, give them an opportunity, and then help them move on to the next thing.”
Caire says that philosophy continued into his work at One City Schools, which he founded after returning to Madison.
Caire, who has five children, notes that his family in Madison goes back generations. “My grandfather’s side goes back to 1907 in Madison, and my grandmother’s side goes back to 1935,” he says. “My grandbabies are going to be the seventh generation of Madisonians.”
But Caire says his family history also illustrates the city’s affordability challenges.
“My kids know all this Madison history but will unfortunately not be able to own a home of their own in Madison because it’s gotten completely unaffordable,” he says
Since he first began considering a mayoral run, Caire says he has met with former Madison mayors and alders, as well as community leaders, to prepare for a potential campaign.
“They’ve been excited to hear that I am running and I’ve been eager to hear their thoughts about the city,” he says. “They’ve seen Madison through many different time periods, but this is a new era where we are going to need some new strategies. I want to be as prepared as possible.”
Caire says he plans to remain in his current position at One City while campaigning.
“I’m gonna stay in my job. I’m not leaving,” he says. “But I will take my last two months of my sabbatical in January, so I can focus on the campaign.”
Four pillars
Caire says Madison is at a crossroads, pointing to rising housing and property costs, city finances and disparities in educational and economic opportunities.
What is missing, he contends, is a clear, shared vision and a mayor who can “cast that vision, mobilize people around it, and serve as a bridge rather than another wedge.”
Caire outlined four major areas of focus for his campaign in what he describes as “a Madison that works for everyone.”
The first is affordability. Caire says he wants the city to become more financially efficient, reduce the burden on residents, and find ways to increase city revenues.
“Madison’s got a tax problem,” he says. “Property taxes are literally funding the majority of the city budget.”
Caire points to the drastic rise in home values and rents, specifically over the last decade, as evidence of the affordability challenges facing Madison.
“What’s happening is housing values are going up, and only people with money can afford to buy a house,” he says. “The rents are going up dramatically, too.”
His second pillar is economic growth and workforce development. Caire says he wants Madison to become an even stronger destination for businesses while expanding the city’s tax base.
He proposes developing six mixed-use cultural and entertainment districts throughout the city as part of that effort.
His third pillar, prosperity, focuses on expanding opportunities for every household, including those experiencing homelessness. He says that he wants to prioritize education, child care and early literacy, ensuring every Madison child reads at grade level and expanding access to successful educational programs.
“We want to provide opportunities and make sure our babies have access to those opportunities, making sure all these kids can read,” Caire says. “If they have access to so many more opportunities, they are going to be confident going through our schools.”
His fourth pillar, community, envisions neighborhoods connected through parks, porches, block parties and lively public spaces, with a mayor who is present and engaged in the community.
“I had a vision growing up here”
Caire is entering the mayoral race with a record that has drawn both strong support and vocal criticism, particularly over his leadership of One City Schools, an independent public charter school. Some Madisonians have raised concerns that charter schools weaken the traditional public-school system.
Caire says he views his personal history as central to understanding his approach and his ambitions.
“First, I would tell [critics] that I am their native son,” he says. “I was the child that we as a city made promises to. I was the racial disparities kid. I was the kid that didn’t have either one of my parents in my life. I was raised by my aunt, my grandparents and others in the community.
“I’m their success story, but yet some people want to criticize me,” he says.
Caire was named a Distinguished Alumnus by the University of Wisconsin Alumni Association for his work in education and community development. He was also the youngest recipient of the City of Madison’s Martin Luther King, Jr. Humanitarian Award. Caire has been honored with the Urban League of Greater Madison’s Whitney Young Jr. Award, which is presented to individuals and organizations who exemplify civil rights leader Whitney M. Young, Jr. as they better the greater Madison community.
Caire says his long family history in Madison gives him a perspective that he believes is important as the city considers its future.
“I grew up here. I had a vision growing up here. My family had a vision of what I could do for the city,” he says. “Elders recruited me back here knowing how much I love this city. “I’m a man who actually made it through fire, and I’m trying to help other people make it through the fire, too.”
Current reporting lists Caire among the candidates challenging incumbent Mayor Satya Rhodes-Conway in the 2027 mayoral race, along with former Dane County Board Supervisor April Kigeya, who launched two weeks ago, and former Alders Syed Abbas and Brian Benford.
Caire says he wants his mayoral campaign to focus on what Madison can become.
“Madison doesn’t have a vision for the city right now,” he says. “And that’s what I can provide. The city still hasn’t lived up to the promise that it made me when I was a kid. But I believe it can. And I believe it will.
“People will thrive here. Now is the time. As a CEO, my job is to always be looking 10 miles down the road. Let’s be prepared for what’s coming next,” he adds. “We have to bring out the best of Madison, Wisconsin. We have the people here; they just need to be organized. This city’s potential is huge.”
