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Kaleem Caire: Change agent
Growing up in Madison, he couldn't wait to leave. He came back with a new goal: to transform it
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'I got out, I was able to succeed, but the whole time it has haunted me. I feel responsible for these neighborhoods.'
'I got out, I was able to succeed, but the whole time it has haunted me. I feel responsible for these neighborhoods.'
Credit:David Nevala

It's 8 p.m. on South Park Street, just off the Beltline, and the November night is dark and cold. But from the inside of the slick new Center for Economic Development and Workforce Training, home to the Urban League of Greater Madison, it looks and feels much warmer.

The first-floor library is packed, with men sunk into plush armchairs with laptops and books and kids gathered near the fireplace. Kaleem Caire looks around, pleased.

"It's nice to go from having very little interest in this part of south Madison to now having this many people coming through here," says Caire, the Urban League's president and CEO. "They feel safe. I'm here at night until 1 or 2 a.m. sometimes."

Caire, 39, is a native of Madison's south side, though he spent the last decade in Washington, D.C. He returned in March 2010 to take the Urban League job, with some trepidation.

"I love Madison," he says, "but I didn't know if it was ready for a creative entrepreneurial leader, let alone a young African American leader."

When Caire first left Madison for the U.S. Navy after high school, he was a disillusioned and angry kid who did poorly in school. Over the last 10 years, he's served on two federal government panels and is at the forefront of efforts to combat racial disparities in his hometown.

That will take some doing.

According to the 2008 State of Black Madison report, 37% of African Americans here live in poverty. The unemployment rate for blacks is 2.5 times higher than for the rest of the community. Black and Latino males have a 52% high school graduation rate and account for 78% of all school suspensions.

Caire thinks the problems run even deeper. He sees a community that is essentially segregated. "I wonder why I see so few white people in Madison spending time outside of work with black people," he says. "How else will they really get to know us?"

That's the kind of bold and arguably impolitic statement Caire isn't afraid to make. He believes Madison is ill-equipped to educate its young people of color, and he's making significant waves with one of his proposed remedies: Madison Prep, an all-male public charter middle school that would be at least 50% black and Latino.

The charter school, as he envisions it, would require uniforms, and at least half of its applicants would qualify for free or reduced lunch. It will also employ non-union teachers, which has predictably drawn an angry reaction. John Matthews, the leader of Madison Teachers Inc., has called it "foolish public policy and a foolish commitment of the public's funds."

But Caire is undeterred, noting that taxpayer money now funds much more dubious causes, like locking up disproportionate numbers of young men of color. "We will fight for this," he vows. "We know these things are needed, and we will do whatever we can to convince people."

There are signs that it's working. At a Dec. 6 school board meeting, where Caire presented his charter school idea, not a single attendee spoke out against it - and many spoke in favor. Word of the proposed school has saturated local news outlets for months, and the project recently won editorial support from the Wisconsin State Journal.

For Caire, it's personal.

"I lost a lot of friends I grew up with here in Madison," he says. "I got out, I was able to succeed, but the whole time it has haunted me. I feel responsible for these men (and women), for these neighborhoods, absolutely. I'm driven by it."

Kaleem Caire was born Michael Caire; he changed his name in 1991 in a traditional African rite of passage. Elder African Americans chose the name Kaleem, which means "good teacher" in Swahili.

When Caire was growing up, his father was in and out of prison and his mother lived on the streets. So he was raised by his maternal aunt Gretchen in the apartments across the street from south Madison's Penn Park. His grandmother was also a constant presence in his life.

"We called it the heart of the south side," says Caire. "All the grownups raised all the kids. Everybody knew everybody. It was a real community."

Caire attended St. James, a Catholic elementary school near Meriter Hospital, through seventh grade, where he was a bright if somewhat mischievous student. It wasn't until 1984, when he entered the eighth grade at Cherokee Middle School, on the near west side, that things started to go downhill.

"I started to see the racial divide," says Caire. "It was a challenge for me from day one."

Whereas St. James had one class for each grade and students from all backgrounds mixed freely, Caire says kids at the much larger Cherokee voluntarily segregated themselves. Even his white friends from St. James that attended Cherokee suddenly now kept their distance.

"Before that, I knew I was black," says Caire, "but I never felt like it was something that other people didn't value until then."

During this time, Caire began skipping school and selling "weed" - actually, pencil shavings mixed with oregano leaves, because neither seller nor smokers really knew what they were doing. It was all posturing, and Caire began purposely acting tough in front of other boys, getting into fights, even getting suspended.

"I hung out with my black peers from the south side, and, unfortunately, most of them didn't have an achievement orientation like I'd had," says Caire. "I got sucked into that behavior because I felt most familiar with that group."

Always interested in art, Caire turned to graffiti, stealing cans of spray paint from Kmart with a friend and tagging structures in the neighborhood. One morning while reading the newspaper (as his aunt and grandmother required him to do every day), he saw his own work pictured under a headline decrying the arrival of gangs in Madison.

"It was so confusing," says Caire. "I started getting scared then, like, these people are going to think I'm a gangbanger."

Growing up, Caire remembers that police were a constant presence in south Madison. He feels black neighborhoods like his were unfairly targeted, and though he recalls many friendly officers, he especially remembers the ones that weren't.

"The police department and the media beat up on the south side so much," says Caire. "I remember thinking, 'These people have no clue what goes on over here. It made you distrustful and bitter."

Still, until that point, Caire's anger was mostly an act. The true anger came when he moved on to West High School, where Caire remembers being the only black kid in almost all of his classes.

"West was a sea of white kids," says Caire. "I walked in and I was totally uncomfortable."

Caire became aware of more subtle forms of racism, like the white parents he says would look right through him. And when he tried to join the yearbook club, the other kids purportedly insisted he'd wandered into the wrong place. There were extracurricular activities he couldn't get to or afford.

"It was all just this inequality," he says. "I just felt we were treated differently."

Caire also remembers the older black kids who took him under their wing, and the history teacher who taught him about Buffalo Soldiers and black cowboys. In his senior year he became a starter on the football team, which enhanced his status among his peers. And all along he had his aunt and grandmother, whose expectations of him were nothing short of lofty.

But for the most part those years were pretty bleak, and when Caire graduated with a 1.56 GPA and an angry heart, he wanted to leave Madison and never look back.

In 1989, immediately after graduating from West, Caire signed on for three years in the Navy and was sent to California. Though it was a difficult transition, the strict discipline and sense of responsibility had an immediate and profound effect. He began reading books to improve his speaking and comprehension skills, and quickly became a leader among his fellow seamen.

"The Navy built up my belief in myself," says Caire. "It was never that you were dumb or incapable. It was always that you weren't living up to your potential. That was new for me."

After a year and a half in San Diego, Caire was charged with choosing his duty station. He had friends at Hampton University in Virginia who were always talking about how pretty the girls there were, so Caire chose nearby Norfolk Naval Station.

Once there, he became deeply involved in a tight-knit group of students focused on African studies. They referred to each other as brother and sister, and the men especially had a tremendous influence on Caire.

"These were the kind of guys who really encouraged you to do the right thing," he says. "To respect women, and to be sensitive and supportive of each other as men."

It was during this time that Michael became Kaleem through a traditional African naming ceremony, and it was through this group of friends that he met Lisa Peyton, on Jan. 6, 1992. She was gorgeous, whip-smart, gracious and strong. Within weeks he knew he wanted to marry her, and just over a year later they wed. He was 21, and she was 20.

Education and self-respect had softened Caire's view toward his hometown, and he missed his family and friends. He and Lisa returned to Wisconsin in 1993, and Kaleem planned to complete a premed degree at the UW-Madison.

Returning to his old environs after only four years, he was horrified by the devastation caused by crack cocaine and his old friends' hopelessness. It was clearer to him than ever that education was the key. He switched his major to urban education and thrust himself into working with neighborhood kids.

Over the next decade and a half, Caire racked up a stunning array of achievements. He spent eight years in Madison serving as a consultant with the Madison school district and the Wisconsin Department of Public Instruction, and coordinator of a UW-Madison campus orientation program. During this time, he received both the city of Madison's Martin Luther King Jr. Humanitarian Award and the Urban League of Greater Madison's Whitney Young Award.

In 2000, Caire moved to Washington, D.C., where he commissioned the nation's first comprehensive study of high school graduation rates for the Black Alliance for Educational Options, and was its founding president. He also worked for Target Corp., as a store team leader and district master trainer; served a five-year appointment on a panel evaluating No Child Left Behind; helped establish a charter school association in the District of Columbia, and lobbied to secure what has grown to $265 million for public, private and charter schools there.

Caire cofounded the nation's first federally funded private school scholarship program, and he was one of 45 reviewers for Race to the Top. He and Lisa had five children and settled into a culturally rich life in Prince Georges County, Md.

"Imagine that," he smiles. "This little black boy from south Madison with the 1.56 GPA."

But Madison was never far from Caire's mind. One day in 2009, while he drove down Washington's Highway 295, his cell phone rang. The voice at the other end was LaMarr Billups, an old friend from Madison who also made the move to Washington, D.C., for a job at Georgetown University. Billups had heard that the Urban League job was opening up and knew Caire would be interested.

"I'd always told him the only thing that could get me back [to Madison] was if this job at the Urban League opened up," says Caire. "And he remembered that."

Caire thought about his rich life in Washington and how nice it was to be near Lisa's family in Virginia. He thought about Next Generation, the nonprofit schools development organization that he was just getting off the ground and that he'd left his job at Target to focus on full-time. And he had concerns about raising his own black children in Madison.

But ultimately, he could not get those other kids out of his head - the ones he had grown up with, and the one he had been himself.

On March 29, 2010, Caire came home to Madison.

Returning to Madison has been, for Caire, a series of bittersweet reunions.

"A lot of the guys I knew and loved unfortunately found their way into the prison system," he says. "Some of them are dead. And some of them are coming in here to see me now, trying to find jobs."

Though Madison is sometimes referred to as "recession proof" and seems to be suffering less in this economy than other parts of the country, Madison's south side is struggling. And that adds urgency to the work of the new Center for Economic Development and Workforce Training.

Besides the Urban League, the center houses meeting space, computer labs, a video conferencing room, wireless Internet and a library. The Urban League offers education on various topics and programs on home ownership and assimilating people of color in Madison. But its number-one priority is employment.

Caire recounts the message he gives to those who come to the center seeking jobs: "We can't do it all, and it's a difficult program to get through. But, man, we want to help you, and we'll do whatever we can do."

But looking into their faces, he says, "a lot of them look defeated." It's a feeling he understands well. And what most bothers him is knowing that defeated boys and men are not born defeated, they're made.

"It breaks my heart, because these guys were bold, gregarious, strong, outgoing, you know?" says Caire. "Now they're too ashamed to go near the families they can't provide for."

Not long ago, one of Caire's childhood friends came in to get started on a program. He told Caire - whom he still calls "Mike" - how glad he was when "you got out of here" and how glad he is now that he came back.

Caire pauses as he recounts the story, his voice gone low and soft. He presses two palms against the pleats of his ivory pants, bows his head a moment and then looks back up, dimples flashing.

"I got teary when he said that. That's a lot of pressure," he says. "But I accept it."

Caire is sitting at the small conference table in his office, but his head often swivels to a framed 8x10 across the room. In the photo, Lisa and Kaleem are seated next to each other. She's wearing red, her long braids loose over one shoulder. She is looking directly at the camera. He is looking directly at her.

"She and the kids are still back in Maryland, but they'll be joining me soon," he says. "She likes Madison, but she also knows that out there our kids know they can be anything."

Lisa Peyton-Caire, associate director of the Educational Opportunity Center at the University of Maryland, has extensive professional experience working with young African American girls. Her own résumé seems to complement her husband's perfectly, including two degrees from the UW-Madison, numerous awards and charter school experience.

And both have, as a result of raising kids in the D.C. area, heightened expectations for what is possible in Madison.

"Out there they have white teachers, black teachers, Latino teachers," says Caire. "African Americans own more than 50% of the businesses in Prince George's County. In Madison, it's less than 1%. It's not okay for our kids to see that. It's not healthy."

Caire believes the Madison community must first address its at-risk population in a radically different way to level the playing field before fundamental change can come.

"Madison schools don't know how to educate African Americans," says Caire. "It's not that they can't. Most of the teachers could, and some do, valiantly. But the system is not designed for that to happen."

The system is also not designed for the 215 annual school days and 5 p.m. end times that Madison Prep proposes. That, and the fact that he wants the school to choose teachers based on their specific skill sets and cultural backgrounds, is why Caire is seeking to proceed without teachers union involvement.

"Ultimately," he says, "the collective bargaining agreement dictates the operations of schools and teaching and learning in [the Madison school district]. Madison Prep will require much more autonomy."

Many aspects of Caire's proposed school seem rooted in his own life experience. Small class sizes, just like at St. James. Uniforms, just like the Navy. Majority African American and Latino kids, eliminating the isolation he grew up with. Meals at school and co-curricular activities rather than extracurricular, so that poor students are not singled out or left out.

Teachers the students can identify with. Boys only, in the hopes of fostering the sensitive, supportive male peer groups so critical to Caire's evolving sense of self over the years.

"Some male schools are very male-centric with a focus on toughness, but boys are fragile," says Caire. "I was fragile, you know? You can't lead young men by just being tough with them. If you have to degrade them, it means you failed them."

Importantly, Caire does not want Madison Prep to be an all-black school. Just as critical to his goal of combating racial disparity is the education of white students.

"Our young white men have to be able to operate in a diverse society," he says. "They have to learn how to develop relationships with young black men organically. All of our young men need to be able to see themselves as stewards of the world."

Caire knows that the road ahead is long, and that many community members are still ambivalent about embracing what he is proposing. But he doesn't lack for confidence in his idea.

"I'm telling you now, Madison Prep will be a school everybody is talking about in five years," says Caire. "When people walk in and see those boys in uniform, see the way they carry themselves, it will bring tears to their eyes. Then they'll all believe."

And long roads are no match for those with the drive and determination to march on. Caire looks again at the photo across the room, and the nearby ones of his children. He turns then, this time to gaze out the large picture window next to his desk, overlooking the packed parking lot.

"I feel like my city threw in the towel with me a few times," he says. "But I will not throw in the towel on it."

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