Roach: Better Man

The world has been dormant for a year. Life as we knew it has been on hold since last March. But in the midst of this latency period, someone has been working. And his name is Kaleem Caire.
Kaleem Caire
Photo Courtesy of Kaleem Caire

The world has been dormant for a year. Life as we knew it has been on hold since last March. But in the midst of this latency period, someone has been working.

And his name is Kaleem Caire.

Full disclosure, I consider Caire and his remarkable wife, Lisa Peyton-Caire, friends.

I worked with Caire when he headed the Urban League of Greater Madison and on his effort to launch Madison Prep, the earnest but quixotic attempt to address Madison’s embarrassing racial achievement gap. The failure to launch that school was a bitter blow. And the gap has remained unchanged.

Madison Prep failed because the teachers’ union and other supporters of the educational status quo were motivated and powerful. But they are not invincible. Caire discovered that the best way to battle those who stand in opposition to righteous change is not to meet them head on, but to adroitly scoot around them.

It also helps to enlist allies.

Allies like the legendary Pleasant Rowland, who just donated $14 million to help address Madison’s stark racial reality by expanding Caire’s One City Schools to a bigger, better building in Monona. Like Caire, I am a Madisonian, born and raised, and cannot think of anyone who’s had a greater impact on our city in modern times than Rowland and her husband, Jerry Frautschi. There is simply no precedent for such philanthropy in Madison’s history. None. Rowland and Frautschi deserve a statue at the head of State Street, once we elect leaders who can figure out how to fix Madison’s shabby aorta.

Caire has other allies, like the UW System’s Office of Educational Opportunity. This entity moved to alter the painful reality that its flagship university is in a town with one of the worst racial gaps in America. So, they chartered One City Schools. Yes, the C word. Charter.

Another ally is Gov. Tony Evers. Long ago and far away, Madison Prep attempted to incent teachers of color to come to Madison with the hope that they would connect with minority students in a way teachers of Norwegian descent might not. The move was stymied by the monied, educational power structure. But justice can win. In November 2019 Evers and the state legislature passed a bipartisan bill to create a program that forgives up to $30,000 in college loans for graduates of color who stay here and teach Wisconsin kids. Wow.

Then, recently, the unthinkable happened. The Madison Metropolitan School District Board of Education acted to remove seniority as the sole criteria for making personnel decisions. This policy has long been an impediment to the recruitment of sorely needed minority teachers and a major sticking point for Madison Prep. The school board should be lauded for an act that can only be seen as courageous, considering the forces arrayed against it.

All of this has come during harsh times for our nation. The previous twice-impeached president stoked racial friction in America by prodding our darkest angels, revealing that we are neither the land of the free nor the home of the brave that we hope to be.

During this strife, and in the dark days of COVID-19, I finally read “The Warmth of Other Suns,” the stunning work by Isabel Wilkerson that won the National Book Critics Circle Award in 2010. It should be mandatory reading for all Americans. It provides a stark reminder of how Jim Crow and its new form of slavery was, and is, alive in America. In fact, the state of Georgia recently gave Mr. Crow a contract extension. I put off reading it for personal reasons. Frankly, the work on Madison Prep had been wholly dispiriting to me. The word despair is apt.

But while some pouted, Caire kept going for another decade. He started One City Schools. He and his staff carried on with fortitude in the midst of a national political climate that revels in pulling us apart and demonizing the poor. His team never shrank from teaching the kids that Madison consistently failed. Quietly and patiently, they’ve continued the work of making Madison less embarrassing to itself.

And now, despite myriad challenges and opponents, Caire’s vision is finally coming true. Through sheer perseverance, he is proving two things I already knew.

He was right all along. And he’s a better man than I.

John Roach, a Madison-based screenwriter and producer, writes this column monthly. Reach him at