Politics
One City Schools founder Kaleem Caire enters Madison’s 2027 mayoral race
Caire says he would center affordability, economic development, education and neighborhood life in his bid to lead Madison. He is expected to challenge incumbent Mayor Satya Rhodes-Conway alongside several other candidates.
Kaleem Caire, founder of One City Schools and a longtime education and equity leader, formally launched his campaign for Madison mayor Monday at the Center for Black Excellence and Culture. He is seeking to challenge incumbent Satya Rhodes-Conway in the 2027 election.
Caire says the city needs a shared plan for its future and leaders able to build support across differences. He has identified four priorities: affordability, economic growth and workforce development, expanded opportunity through education and child care, and stronger neighborhood connections.
On affordability, Caire says Madison should make city finances more efficient, ease residents’ costs and find ways to increase municipal revenue. He argues that rising home prices and rents are making it harder for longtime residents to remain in the city. For economic development, he proposes creating six mixed-use cultural and entertainment districts and expanding the city’s tax base.
His education agenda includes early literacy, child care and ensuring children can read at grade level. Caire also says he wants to broaden opportunities for households experiencing homelessness. His vision for community life emphasizes public spaces, parks and neighborhood gatherings, alongside a mayor who is visible in residents’ communities.
Caire grew up on Madison’s South Side and returned to the city in 2010 to lead the Urban League of Greater Madison after working in education-related roles on the East Coast. He founded One City Schools in 2014. He says he plans to keep his role there while campaigning, taking the final two months of a sabbatical in January to focus on the race.
His candidacy is likely to draw scrutiny over One City, an independent public charter school. Some residents have argued that charter schools can undermine traditional public schools; Caire has defended his record and says his own experience with racial and economic disparities informs his work.
Caire says his family has lived in Madison for generations, but worries his children may not be able to afford homes in the city. He joins a developing field that includes former Dane County Board Supervisor April Kigeya and former Madison alders Syed Abbas and Brian Benford, according to the information provided.