This week, we are profiling Kaleem Caire, the extraordinary founder and CEO of One City Schools in Madison, Wisconsin.
In 1909, Laurence Clifton Jones learned about the illiteracy rates in Rankin County, Mississippi. He had recently graduated from the University of Iowa and, upon learning that 80% of the county was illiterate, traveled 750 miles south from Iowa with $1.65 to his name. He made it his life’s mission to educate the children of poor Black sharecroppers in the rural South — not fighting for himself, but for the generations to come.
Jones started Piney Woods School in Rankin County with a single student. Now, it’s one of the few remaining Black boarding schools in the country. It’s lasted over 100 years and has a 100% graduation rate.
Its success has led to a new documentary about the school being released this year.
In the same way that educators today are being inspired by the story of Piney Woods, so was Kaleem Caire inspired by the school, only his inspiration came decades ago when he saw a BET report about Black independent schools in the South — schools like Piney Woods.
“Seeing how students carried themselves, how they felt a part of the school, you could see they had a future,” Kaleem said.
That was different from much of what he had experienced at his own high school, where he rarely had classes with fellow Black students and often felt as though Black students were neither valued nor taken seriously. But in seeing this BET special, Kaleem said he “saw a way forward for us that I hadn’t seen before, and I wanted to be part of that.” He’s been fighting for that way forward since.
Reinventing Public Education
After serving in the United States Navy, Kaleem made his way back to Wisconsin, his home state. He was committed to improving urban education, working with and learning from education icons like Howard Fuller and Gloria Ladson-Billings while at the University of Wisconsin. Through his studies, he came to believe in the necessity of reinventing public education — viewing charter schools as a key vehicle for that reinvention.
Kaleem ran for school board and attempted to launch a charter middle school and high school in Madison, Wisconsin all unsuccessfully. This was a tough point in his career. But in that process, he heard from many in the community: “Why don’t you start earlier, Kaleem?”
Starting Earlier
In his fight for the reinvention of public education, he hadn’t much considered the role of the very youngest students. But after listening to his community and visiting dozens of charter schools across the country — including Geoffrey Canada’s Harlem Children’s Zone — Kaleem decided that reinvention of education should start with the littlest learners.
In 2015, One City Preschool opened its doors to eight students in Madison. By beginning with students as young as two, Kaleem hoped to create an entirely new educational system that would build on learning successes from students’ earliest days. In beginning to educate children while they’re young, One City sought to also build relationships with their families, working alongside them and their communities to address their needs.
That preschool was welcomed by many families, leading to One City’s expansion and supporting what One City calls the “Two-Generation School Model” — the belief that the success of children is tied to the health and trajectory of their families.
The Two-Generation School Model
One City Elementary School, a charter school that serves children in 4-year-old kindergarten through seventh grade, was approved in 2019. In 2023, One City Preparatory Academy, a charter school serving seventh and eighth graders, was approved.
And the “Two-Generation School Model” is thriving. It’s typical to see 70% or more of families represented at school events. Parent-teacher conferences regularly get 100% participation, and parents are members of One City’s Board of Directors. In addition, One City has helped families access job training, mental health counseling and financial planning. They’ve even launched a home ownership program that 21 families or staff members have participated in, and they have a credit union housed in their building.
For Future Generations
The spark was lit by Kaleem’s own experiences and a BET special. Now, his life’s mission is in action. “I’m proud of all that we’ve been able to create. We’ve been able to create this dream and this new model of what school can be,” he said.
Charter schools, he said, are a vehicle for doing more of this. And he wants charter school leaders to get more “jazzed up” about advocacy. “There is a higher purpose for your work that you might not even recognize yet,” he said. “You’ve gotta advocate.”
Like many educators, Kaleem has a sincere, motivating belief that every child deserves to be effectively prepared to succeed and to lead an enriching life. That, he believes, will build a better world for future generations. Indeed, the heartbeat of his work is very same as the one that led Laurence Clifton Jones to create Piney Woods School: “You’re not fighting for you — you’re fighting for the generations that you’re educating and the ones coming up behind them.”