Hardly Child's Play

Urban League president Kaleem Caire refuses to fail Madison's youth

When asked to describe himself, Kaleem Caire laughs: “Relentless. Focused. Determined. And no bullshit.” He pauses for a moment before continuing: “I can’t figure out a better word to say that, but these people that we serve don’t have much time. Let’s not sugarcoat things. When I say ‘no bullshit,’ I mean, let’s put everything on the table.” His voice doesn’t quite boom, but it does register evenly as a baritone.

A year ago, after a decade living on the east coast and working in Washington, D.C., the 39-year-old Caire returned to Madison to helm the Urban League of Greater Madison. He worked for national nonprofits like the American Education Reform Council and major corporations, like Target, and has returned with big-city bluster and big ideas.

In his first month on the job, he sought statistics from the school district about graduation rates for black students, a woeful percentage that before then was not widely publicized. Although the Urban League primarily focuses on job training, most publicly Caire has stormed back into his hometown with a proposal to open a charter school for boys, Madison Preparatory Academy. Students will dress sharply in red blazers and pressed whites. It will be a challenging International Baccalaureate curriculum and cater to underserved and often under-achieving minorities. He is also proposing a sibling all-girls high school.

For a city convinced, if not complacent, that their public schools excel, the idea that the school system may be failing a large number of local teens is shaking accepted norms.

What is the mistake people most often make about you?

Some people think that I came from this wonderful, easy family, and they are shocked to hear that my dad was in prison eight times. I only met the guy in 2004. He was coming out for his seventh time, and heading back in for his eighth. He told me that I was fortunate that my aunt raised me.

My mother lived most of her life in a bus shelter. You know the Starbucks on State Street? The bus shelter across the street? I grew up not knowing what shape my life would take. Man, I was confused.

But ultimately that shaped your life?

Yes. But I think that people also mistake my passion, and think that I’m an activist. I’m really not. I just don’t like to see people fail. I’ve seen it too much in my life. It is diminishing to the spirit. It is not about African Americans at all costs to me. It is about the community.

So, after graduating from West, you went off to college?

No, I had terrible grades in high school. I was coming home one night. I was on the bus, because we didn’t have a car. It was March or April of my graduating year, and I didn’t know what I was going to do. The dream of a scholarship for football had been appropriately shattered, and I saw that sign, “Be All That You Can Be,” and there was a recruiting depot by Demetral Park on the east side. I got off the bus and walked in. The Navy guys invited me to have doughnuts and
coffee. We chilled for two hours.

Had you been on boats before?

Little-bitty boats. Lake Monona boats. I ended up in the Submarine Corps as a sonar technician. I was the eyes and ears of the ship. I loved it.

Do you consider the Navy your lucky break?

I do. It eventually paid for my education. People had always told me I was a leader, but for the first time ever, the Navy defined what that meant. It was a drumbeat. They talked about it all the time, so I was able to judge myself against the definition of leadership every day. It was also the first place where I was told that I was an under-achiever. I wasn’t told that I was a low achiever, but that I wasn’t achieving my potential. It was motivating. It wasn’t pressure to fail, but it was an expectation. I’m a competitive person, and it made me want to work that much harder.

And this plays into the discipline and philosophy of Madison Prep?

Absolutely. I saw myself and a whole lot of other young guys without any direction whatsoever. We didn’t know that we were smart, and those are some of the most talented people I’ve ever seen.

So, eventually, after the Navy and a few years of school in Virginia, you returned to Madison to finish college, find a job, raise your family. Why’d you leave again?

After several years back, my wife [Lisa] and I were ready to move. Both of us felt like our growth opportunities were stunted here. My wife was working for the state. There are plenty of government jobs, but I call them wait-in-line jobs. Unless you get an appointment by the governor or the mayor, you wait. We saw that we had more capacity to make change elsewhere.

And now, for a second time in your life, you’ve come home.

I had heard that this job had come up. It is the only job I would have come back for. I didn’t tell my wife for the first few days because she struggles with Madison. She loves it. It’s beautiful here, and she likes the lakes. But as far as opportunities for black women and the way she was treated when we lived here before, it was hard for her. She didn’t like walking around with our kids and people looking at her as if she were a single mom. [Lisa and the kids will move here this summer.]

This time around seems like a different homecoming.

Last time, Lisa cried half the way here. Professionally and culturally, the D.C. area is absolutely the best area in the country for black women. My wife has opportunity to grow there. She works in higher education, as the director of the educational opportunity center at the University of Maryland. Her whole focus is to get adults back into school or to work.

Whatever she does, I just hope that she is happy. It is a sacrifice for both of us. What I’m looking for right now is a way to make an impact, but I also want to prioritize my family. In D.C., I was on the road an hour and a half each way and that compromised my ability to spend time with my own family. I’ve always prided myself on being intensely engaged in my kids’ lives. I was a soccer coach when I lived here last time, and then my first year in D.C., I only went to two school events. When you ask who am I accountable to? To my family and my community.

So, what do your kids think about Madison?

They are okay with it. Well, two of them are. The oldest has a peer group out there and is into the arts. His concern—and we share it—is that people here aren’t really going to open doors.

Which brings us back to the charter school, right?

It is sixth through twelfth grade. It is an all-boys school, but also we plan to start an all-girls school. It will be an International Baccalaureate curriculum because our kids need to know that they are part of a bigger world. It is very rigorous. It is very analytical. It helps you learn how to think, and not just about what to know, but how to shift paradigms. Ultimately what we want are kids who are ready for college, and also are ready to change the world and not just be passive participants.

Because we highlight the problems that African American males are having, people assume that it is going to be an all-black school. It isn’t. It should be 30–35 percent black. Outside of that we will have Latino boys; we will have white young men; we will have Asian kids. You can create a type of environment where all these young men can achieve. Madison Prep will provide the environment so that these young kids will feel valuable and held to and coached to high expectations. We need to build confidence.

Yes, I am concerned about the racial achievement gap, but at the same time I’m concerned about the gap between the talent we produce and the type of jobs that really will be available in the next ten years.

Why not integrate a program into an existing school?

Madison has seen isolated examples of one or two black students in a class who challenge for the highest honors, like class valedictorian. But they are seen more as an enigma than the status quo. We need to produce a school where all of these boys are going to college.

What is your main obstacle?

Courage and gross commitment to the status quo. There are still those who don’t want to come out publicly and support the idea, which to me means: I don’t want to be on that boat when it tips over. But if we were all on that boat together pushing and paddling, we would be successful, and our kids would be successful.

You are not even a year into the job at the Urban League, but have you thought about what your legacy will be?

Yeah, to change Madison, to make it a place where everyone can succeed. I won’t just be comfortable with helping 2,000 people get jobs. Ten years from now, when I’m assessing my impact, I want to consider how many doors that were closed have now been opened, and how many senior black executives we have and how many diverse cultural events we have. Also, I want to look at, are we African American leaders modeling behavior we want to see elsewhere? I want to have a much bigger impact than here at the Urban League—and I have to. I can’t just rely on the charity of people. I have to change behaviors.

Phil Busse is a writer who recently returned to his hometown, Madison. He is also executive director for the Media Institute for Social Change (MediaMakingChange.org).

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