Meet Kaleem
Madison’s native son.
I was born here and raised by family and neighbors on the South Side. For 30 years, I have built schools, jobs and opportunity for the city that raised me. Now I’m running for mayor.
- Fifth-generation Madisonian
- U.S. Navy veteran
- UW–Madison graduate
- Father of five
My story
By the odds, I should have become a statistic.
My mother struggled with homelessness, and I met my father only twice. At two, I was taken in by my aunt, Gretchen Caire. We lived across from Penn Park, where my grandmother, Mary Caire, kept me close and never let me forget that school mattered.
Our neighbors did the rest. On the South Side, the grownups raised all the kids. Madison raised me, and I will forever be grateful. Every child in our city deserves that kind of village.
Service runs in my family.
1867
John Pierce
My great-great-grandfather. Born into slavery in 1815 in Virginia, he was sold to a North Carolina plantation owner who relocated to Louisiana. After Emancipation, he was one of 49 Black men who participated in rewriting Louisiana State Constitution during Reconstruction (1867–68). He was twice elected to the Louisiana Legislature, led Jefferson Parish, and served as the Parish Police Juror.
1829–1944
Hettie Pierce
My great-great-grandmother. Born into slavery in North Carolina, she died in Madison in 1944. The Wisconsin Veterans Museum honors her as one of the oldest people to have lived in Wisconsin.
Five governors
Samuel Pierce
Their son, my grandfather’s uncle, served as executive messenger to five Wisconsin governors, including three Republicans, a Democrat and a Progressive, from 1925 until he died in 1936. He was known at the Capitol as a bridge-builder and was one of the most well-known and respected African Americans in Wisconsin.
1982
Mary Caire
My grandmother founded the Bram’s Neighborhood Association and received the City’s Martin Luther King Jr. Humanitarian Award. Eighteen years later, I became the youngest adult to receive it.
My record
30 years of building.
From the South Side to the Navy, Washington and back home: every chapter prepared me to lead Madison.
1971 · Madison
Born and raised on the South Side
I was born at the old Methodist Hospital and raised by my aunt and grandmother across from Penn Park. I went to Franklin Elementary, St. James, Cherokee Middle and Madison West, where I was often the only Black student in my college-prep classes.
1989 · U.S. Navy
A second start
I graduated from West in 1989 with a 1.56 GPA. The Navy gave me a second chance and taught me I was never incapable, just not yet living up to my potential.
- 96recruits I led through boot camp at 17
- USS Jacksonvillefast-attack submarine where I served as a sonar technician
1993 · Madison
Coming home
I came home to start a family and finish my education. Walking across UW–Madison, I saw very few students of color, and I knew what I would do with my life. I earned my education degree and went to work for Madison’s children, helping build the program that became the Schools of Hope tutoring program.
- 200+Dane County teens I placed in summer jobs
- 3Madison elementary schools where I coached reading
- 2000City of Madison MLK Humanitarian Award
2000 · Washington, D.C.
What I learned in Washington
In 2001, as founding president of the Black Alliance for Educational Options, I commissioned the first comprehensive study of high school graduation rates in the United States. Today every public high school in the country reports an honest four-year graduation rate. I learned that good intentions only matter when the work gets done.
- $40Min new federal funding for D.C. students in year one
- $1.3B+for D.C. schools as Congress renewed it for 20+ years
- Last → 1stthe Target store I ran, in total store operations
2010 · Urban League
Bringing it home
I returned to lead the Urban League of Greater Madison and focused on jobs, because a good job changes an entire family. More than 900 volunteers tutored 2,500 children.
- 183 → 1,700+adults served in four years
- 18 → 73employer partners
- $17.2Mearned by our graduates, combined
2014 · One City Schools
Building the school I wish I’d had
I founded One City Schools on the South Side: a public charter school for infants through 8th grade, with longer days, two teachers per classroom through 2nd grade and a healthy meal for every child. In Wisconsin’s latest report cards, both of our schools exceeded expectations.
- ~95%of our preschool graduates enter kindergarten ready
- #1in Dane County for middle school academic growth
- 32One City families and staff who bought their first home
2023 · State Capitol
Moving an agenda
I organized a bipartisan statewide coalition to raise per-student funding for Wisconsin’s independent charter schools. We won, and the same budget deal added $1 billion in new aid for public school districts. I work with Democrats and Republicans alike.
- $9,264 → $11,000per-student funding in the 2023–25 budget
- $1Bin new aid for public school districts
2026 · City Hall
Why I’m running
Housing, jobs, child care, safe streets and transit decide whether a family can thrive here, and they are built at City Hall. My story is proof that Madison can raise its own talent. My vision is simple: make Madison the best mid-size city for everyone to live, learn, work and thrive.
Why I’ll be an effective mayor
Six tests of a strong mayor.
The best mayors don’t solve every problem alone. They build a city capable of solving its own problems. Here is my record on each test.
Vision
Does the city know where it’s going?
One vision, four pillars, stated clearly: Affordable, Healthy, Prosperous, Together.
People
Can the mayor build and lead a strong team?
Built One City to 100 staff and a $13 million budget, led 48 staff at the Urban League and trained 76 Target executives across seven stores.
Execution
Does the work get done?
Took a last-place Target store to first in three and a half months, grew Urban League job training nearly tenfold in four years and built One City in a state that underfunds public charter schools and early childhood.
Partnership
Can the mayor inspire people outside of City Hall to support Madison?
Won funding from Congress, the Legislature and the City, and served as an education reviewer under Presidents George W. Bush and Barack Obama.
Stewardship
Is public money handled with care?
Ran One City on about half the public funding per student that district schools receive, closed the gap with private support and earned multiple years of clean audits.
Trust
Do people believe their government listens?
Reached 18,500 D.C. parents door to door and built parent engagement into every One City classroom.
In others’ words
The Kaleem Effect.
In 2015, Madison Magazine’s “The New Face of Madison Leadership” gave a section to “The Kaleem Effect”: leaders across the city said his work at the Urban League moved them to lead.
“I watched Kaleem, and I said this community is ready.”
“…he diligently advocates while maintaining the highest level of respect and regard for those who may hold divergent opinions.”
Kirbie Mack, chair of the City of Madison MLK awards committee. The Capital Times, January 14, 2000 “Caire not only offered a solution, he also shined a bright spotlight on the achievement gap and inspired a legion of advocates who won’t let it be dimmed anytime soon.”
InBusiness Magazine, “25 Most Influential People in Greater Madison,” 2014 “He’s an above-and-beyond innovator, even in the charter school space.”
Madison Magazine, Best of Madison Business, 2022
Recognition
Recognized across Madison and beyond.
2026
Power100 Business Leader, Greater Madison
InBusiness Magazine
2025
Wisconsin Innovation Award (One City Schools)
Wisconsin Technology Council
2018
LaMarr Billups Community-University Engagement Award
UW–Madison Chancellor
2014
25 Most Influential People in Greater Madison
InBusiness Magazine
2000
Dr. Martin Luther King Jr. Humanitarian Award
City of Madison
1991
National Defense Service Medal, Persian Gulf War
U.S. Navy
All honors (37)
- 2026Power100 Business Leader, Greater MadisonInBusiness Magazine
- 2025Wisconsin Innovation Award (One City Schools)Wisconsin Technology Council
- 2024Power100 Business Leader, Greater MadisonInBusiness Magazine
- 2024Finalist, Mid-Sized Business of the Year (One City Schools)InBusiness Magazine
- 2023Certificate of Recognition for creating the Foundations Central programUrban League of Greater Madison
- 2022Brian Howell Excellence in Innovation AwardMadison Magazine
- 2021Gold Award, Best Single Editorial or OpinionMilwaukee Press Club
- 2018LaMarr Billups Community-University Engagement AwardUW–Madison Chancellor
- 2018Presidential Eagle Award for Exceptional Vision and PerseveranceMadison Black Chamber of Commerce
- 2018Distinguished Community Service AwardMadison Metropolitan Chapter of The Links, Inc.
- 2018Pahara-Aspen Education Fellow; Global Network of LeadersPahara Institute and Aspen Institute
- 201644 Most Influential African Americans in WisconsinMadison365
- 2016M-List: Mentors and Teachers AwardMadison Magazine
- 2016Excellence in Educational and Community Leadership AwardCharles Hamilton Houston Institute
- 201425 Most Influential People in Greater MadisonInBusiness Magazine
- 2014First Donald Driver “Driven to Achieve” AwardDonald Driver Foundation
- 2014Legacy AwardFoundation for Black Women’s Wellness
- 2014Inspiration AwardUrban League Young Professionals
- 2014Editorial board recognition for leadershipWisconsin State Journal, Capital Times, Madison Times, Umoja
- 2013Candace and Charles McDowell Alumni Achievement AwardUW–Madison
- 2012Muriel Pimpkins AwardMentoring Positives
- 2012Commitment AwardNiagara Foundation
- 2012Best of Wisconsin Business Award, Philanthropy & Community Service (Urban League)Best of Wisconsin Business
- 2011Citizen of the Year (District 9 and Gamma Gamma Gamma Chapter)Omega Psi Phi Fraternity
- 2011Five People to Watch in 2011Wisconsin State Journal
- 2008Forward Under 40 Award (among the first honorees)Wisconsin Alumni Association
- 2008Distinguished Alumni LecturerWisconsin Alumni Association
- 2004Letter of AppreciationU.S. Secretary of Education Rod Paige
- 2001Whitney M. Young Jr. Equal Opportunity AwardUrban League of Greater Madison
- 2000Dr. Martin Luther King Jr. Humanitarian AwardCity of Madison
- 2000Certificate of AppreciationBoys & Girls Club of Dane County
- 1999Leader for the New MillenniumThe Capital Times
- 1999Future Leader of MadisonIsthmus
- 1991National Defense Service Medal, Persian Gulf WarU.S. Navy
- 1991Letter of Commendation for Service and PerformanceU.S. Navy
- 1990Letter of Commendation for Physical FitnessU.S. Navy Submarine Warfare Command
- 1989Best Foot Forward Award, Recruit Chief Petty Officer, Company 214U.S. Secretary of the Navy
Appointments
- 2001–03Federal charter schools program reviewer
- 2002–07U.S. Department of Education independent review panel on Title I and No Child Left Behind
- 2009–10Race to the Top expert reviewer
- 2011–17National Association of Charter School Authorizers advisory board
- 2013–14U.S. Senator Tammy Baldwin’s Service Academy Selection Committee
- 2013–19Member and chair, Edgewood College Business School Advisory Board
- 2016–presentUW–Madison Chancellor’s Advisory Council
- 2019–presentWisconsin Technology Council board
Ready on day one
I haven’t run a city government. No first-time mayor has.
But I have built organizations from the ground up, turned around ones that were falling short, and delivered results with partners who didn’t report to me. On day one, I’ll hire an experienced team of Deputy Mayors, keep the City’s professional staff doing what they do best, and focus where a mayor matters most: setting priorities, strengthening services, building partnerships and making sure City Hall delivers.
“Leadership, particularly political leadership, is not about power and winning. It’s about improving the lives of rank-and-file citizens.”
Kaleem Caire, Isthmus, 1999