Close friends of Kaleem Caire describe his aspirations as “crazy.” His story explains why.

Kaleem Caire grew up on the South side of Madison and graduated from Madison West High school. With a 1.58 GPA, Caire barely passed the mark.

After Caire spent three years in the Navy, he was released early due to an injury and decided to take a leap to attend Hampton University in Virginia.

He eventually graduated from the University of Wisconsin with a 4.0 and honors — a far cry from his academic standing when he walked across the Madison West stage after high school.

During his time at UW, Caire changed his path from becoming a doctor to becoming an educator based on the mentorship he received from staff. It was also at UW that Caire noticed the paths his peers were going down, including abusing substances and dropping out of school.

While Caire found his footing after high school and dedicated himself to his college classes, he realized some of his classmates could not do the same since they never made it to college.

The education system had failed his peers long before when they were in high school.

Since then, Caire has made it his life mission to reform Madison’s education system — as “crazy” as it may be.

“The things that Kaleem is trying to do, at the scale he’s trying to do them … He’s not trying to make incremental improvements,” One City Schools Co-Founder Vivek Ramakrishnan said. “He really is trying to change fundamentally what is happening in Madison and Wisconsin. The lengths to which he will go to make that happen are crazy.”

Together, Ramakrishnan and Caire’s mission to improve education in Madison is on its way to being realized through their passion project — One City Schools.

One City Schools operates as a nonprofit, tax-exempt public preschool and grade school that is working to change the common approach to educational methods. As achievement gaps persist across all levels of education in Wisconsin, One City Schools attempts to traverse a challenging landscape and create an educational system that ensures success for youth in the community and beyond.

Caire’s work

Caire has carried a “pedal to the metal” attitude with him throughout his life. This attitude proved pertinent when he took an education research position with UW after graduation, when Caire discovered the extent to which students of color were dropping out and not attending school.

At the time, it was believed that the high school dropout rates among Black and Latine students were around 16% to 17%. But after conducting further research and calculations, Caire said they learned that only about 50% of Black and Latine students were graduating from high school.

Caire said the other researchers were shocked by the numbers. While the numbers didn’t surprise him, he said they reinforced just how much work needed to be done.

Caire said it was difficult for him to see his friends and peers growing up and not using all of their capabilities. It was equally hard when he started to realize that the system wasn’t really built to help Black people succeed.

Wisconsin has seen significant disparities between Black and white students for decades, including in the achievement gap, graduation rates and school suspensions.

Caire knew he needed to do something.

“I tell people that was a vision I’ve had since I was 17 years old, trying to figure out how to start a school,” Caire said. “I realized all the work I was doing with research and community programs and schools was all preparing me for that moment when I started One City.”

Propelled to action following his research with UW, Caire went to talk to Howard Fuller in Milwaukee about the next steps to make his teenage vision a reality. Fuller is a professor of education who is known nationwide as a civil rights activist and education reform advocate. He specializes in work to ensure equitable education for Black children.

With similar views and goals for the future of education, Caire believed that Fuller would be able to offer him advice.

“Dr. Fuller had said to me, ‘You know Kaleem you’ve got two options,’” Caire remembered. “He said, ‘You can try to do this from the inside, or you can do it from the outside.’”

While he spent time with Fuller, Caire observed the options for charter, public and private schools that used voucher programs in Milwaukee to tackle the problem from the inside. 

The first independent charter school that Caire proposed in Madison was shut down by residents. In 2014, he was approached by a group he was involved with at Child Development Inc. The center was soon going out of business and asked Caire if he would take over their school to help keep childcare in the community.

Child Development Inc. knew of Caire’s goals to create a new school system in Madison, so the group gave Caire the opportunity to use their foundation to launch his own mission.

In 2019, the UW System officially approved Caire’s vision of One City Schools as a public charter school. Now, as the founder and CEO of One City Schools in Madison, Caire is able to put his vision for education into practice on a large scale.

“My career has been interesting, and it’s been intense and impactful, but I’m glad to be home and finally getting this opportunity to do One City,” Caire said.

One City Schools’ mission

Ramakrishnan said Caire is particularly good at getting people behind his mission and doing whatever it takes to help it along the way — even if it means getting down and dirty.

Ramakrishnan meant that quite literally. Before One City had the funds to hire a full-time custodian, Caire cleaned the school building after hours by himself for a year.

Ramakrishnan said one reason Caire is such a respected leader is that he “does not ask anyone to do anything that he himself is not willing to do.”

Originally, Caire focused primarily on reducing the achievement gap between students of color and white students in Madison. The achievement gap has been a longstanding problem in Wisconsin. In 2019, the year One City was approved by the UW System, Wisconsin had the largest achievement gap in the nation.

But Caire has since expanded his mission to educate kids on a host of issues that will impact their lives in the future such as global warming, access to clean water and navigating the digital age.

Caire said these life-changing topics are ones that other schools are not tackling in-depth. Though other schools are not discussing how these issues will need to be addressed in the future and how students’ lives will be impacted, Caire believes these are the topics students need to be learning about.

“I’m going beyond focusing on the gap and now I’m trying to really use One City to create a new model of education in America,” Caire said. “I really want to support our children but also prepare them to tackle these big issues later.”

For now, Caire and One City Schools are executing these goals through the organization’s two schools. The enrollment for the 2021-22 school year is at 162 students between the two institutions. One City’s preschool operates as an early childhood learning center, serving kids from two to four years old. Their elementary school serves kids from four-year-old preschool through fourth grade.

The goal is to build the schools to serve an additional grade level each year, until middle and high school levels are also represented at One City.

Tackling a broader issue

One group at UW that is working to address the gaps that Caire hopes to eradicate is Matriculate. In many ways connected to the achievement gap, another pertinent disparity that exists in education is the gap between students who are applying to college.

To address this problem, Matriculate works to inform and give low-income, high achieving students the resources to apply to college. Matriculate’s advising fellows at UW pair up one-to-one with high school students to mentor and support them during the college application and selection process.

Matriculate Head Advising Fellow Maggie Riordan said many of these programs aim to give students the resources, support and confidence they need to make the college decision that is best for them.

“Matriculate’s idea is that the majority of high achieving, low-income high school students don’t apply to the same reach colleges or best-fit colleges that students of higher incomes apply to,” Riordan said. “Through mentorship and that one-on-one relationship they have with their advising fellow, we teach them how to build a college list and gain the confidence they need to apply.”

Riordan said mentoring occurs on a student-by-student basis, as it allows individuals to connect with their advising fellows and receive support from a peer as they need it.

These kinds of programs exist because of the educational and social divide between certain students and their peers, Riordan explained.

“Matriculate is filling that gap that exists in resources that students have to apply to college and support they have. Because those resources don’t exist already, Matriculate and other nonprofits try to fill that gap,” Riordan said. “That gap shouldn’t exist in the first place.”

The gap that exists between students in the college application process is a gap that Caire is also trying to systematically address from a young age through One City Schools.

One City Vice President of External Relations Gail Wiseman said their young students have a solid foundation to succeed later in life because of the curriculum and philosophy of One City.

“I do think preparation begins immediately,” Wiseman said. “I don’t think it waits until middle school or high school. I think the solid foundation they’re getting with critical thinking and problem solving already at the preschool level feeds into further curriculum.”

Though One City Schools only function as a preschool and grade school today, Caire’s near-future plans involve expanding into a middle and high school.

At the high school level, One City plans to partner with universities to create programs that allow students to take college courses as early as their freshman year of high school. Through completing this programming, students may only need to attend college for one year before receiving their degree.

“We currently have a school developer looking at those [upper grade levels],” Wiseman said. “I don’t think we’re going to land on one program; I think we’re going to land on the best parts of different programs to create a hybrid of different programs. We want the programs that are going to help prepare the leaders for tomorrow.”

Effects of a new design

Toya Pedracine-Stewart is a parent and board member at One City Schools. Pedracine-Stewart has been a One City parent for four years and currently has one child enrolled at the school.

Pedracine-Stewart said the staff at One City are especially good at knowing students’ personalities and helping them shape their unique talents. With a staff that is diverse in race, culture and background, Pedracine-Stewart believes her daughter sees that she can be and do anything she wants.

“One City gives [my daughter] the opportunity to see that in life, when people say you can be what you want to be when you get older … they bring that vision into reality,” Pedracine-Stewart said.

Pedracine-Stewart appreciates that at One City, students are not only lectured in order to learn curriculum content. Students can be creative, complete hands-on projects and work with their peers in order to foster an environment of sharing ideas and opinions. Much of the curriculum that One City has adopted centers around working in groups to problem solve and complete projects.

Wiseman said that because young children’s brains are developing at such a rapid pace, it is important to expose them to real world situations and ways to solve issues.

“Access to these kinds of tools will make all the difference in the world,” Wiseman said. “Giving children a foundation as a way to handle their relationships and so many different parts of their lives can’t do anything but good. It seems like a wonderful approach to me, and that’s what they do all day long.”

In the classroom, Wiseman said teachers actively seek opportunities to have their students problem-solve and work as a team.

For example, Wiseman was in one of the kindergarten classrooms recently when one student didn’t want to share with another. Instead of simply telling the student to share, the teacher asked the students to reenact the situation in front of the class so the whole class could work together to solve the situation.

Wiseman said no one made any of the students feel badly about their actions. Instead, the disagreement was simply a situation that the team needed to overcome.

This ability to share ideas and opinions is especially important in a community like One City where the strong diversity brings in people from many different backgrounds.

“Regardless of what our experiences or background has been, as parents and as people we are so much alike,” Pedracine-Stewart said. “One City, like the name, truly creates an opportunity to feel like it is our One City community.”

Expanding the model

Wiseman said One City’s hope is that other schools will adopt the same philosophy and programs that they have built.

“There’s no inferior or superior kids,” Wiseman said. “Everyone is doing their best and everybody is there because they’re supposed to be there. That’s the philosophy, and I think it really helps the kids.”

Ramakrishnan explained that generally non-profit organizations are thought of as being risk averse and predictable in the steps they take to grow. But this is not the way Caire has operated with the way he built One City Schools.

“Some of the risks we take operationally and business-wise … some of the bars he sets are crazy aspirational-wise,” Ramakrishnan said. “The guy does not play it safe. Kaleem doesn’t lower his bar.”

One City Schools currently has two projects underway that are big steps forward in Caire’s plan. With a building they’ve recently purchased, One City will add a 157,000-square-foot addition to its campus which will include more grade levels. The organization will also be building a new athletic facility on their existing property.

Caire explained that these kinds of strides are only possible because the people of One City come together in community to support their children. Though there are many different backgrounds, cultures and beliefs at One City, everyone comes together for the betterment of the students.

Caire hopes the climate he has built at One City translates into the greater Madison community. And with his aspirational tone and booming laugh, it is easy to see how Caire has built the community and made the progress he has at One City.

“I tell people I’m a social architect in that I build solutions to solve these big systemic problems,” Caire said. “I want to create a new world of opportunity for our young people all around the world.”