Dylan Brogan
Cheatham, who will leave in August to join the Harvard faculty, says “the school district is in very good hands.”
In March, Jennifer Cheatham confessed that it had been a “trying” school year for her as the Madison school district’s superintendent. There had been several high-profile incidents involving student safety and teacher resignations as well as growing racial tension. For two years, school board meetings have been dominated by a push from Freedom Inc. to remove Madison police officers from four of the district’s high schools.
On May 8, Cheatham reiterated that there “have certainly been some challenges this year. There are in every school year.”
Nevertheless, she insisted at a news conference where she formally announced her resignation that the challenges are “absolutely not the reason why I am leaving.”
Instead, Cheatham says she’s leaving because it’s a “natural point of transition.” In the fall, she’ll join the faculty of the Harvard Graduate School of Education “to help prepare the next generation of equity leaders.”
“I’m ready to make a larger impact on the education field,” said Cheatham, who joined the district in 2013. “Quite honestly, I’m thinking a little bit more about the support I want to provide my own family and my child…. I’d like to be a little bit more of a mom, too.”
Cheatham said the Strategic Framework, which guides district policy and was updated in 2018, has laid a strong foundation for the district and she’s confident “the school district is in very good hands.”
The Madison school board is expected to appoint an interim superintendent by the end of May. Board President Mary Burke, who spoke at the news conference, said the board hasn’t made a decision yet but it is leaning toward an internal candidate for the temporary post.
“We don’t want to miss a step here. We have important work to do,” she said. “We need to keep the momentum going. Having someone who is already familiar with that work, knows the staff, has those connections — is probably the best person to serve in that interim role.”
The search for a permanent replacement for Cheatham hasn’t been discussed by the board yet, Burke added. “The board will undertake a thorough process. There is no more important duty that the board of education has than choosing its leader.”
Recently elected school board member Ali Muldrow says she’s focused on finding a superintendent that “has an incredible drive, a sense of equity and is immensely talented.”
“I think the real story isn’t that Jen Cheatham is resigning, it’s that Jen Cheatham has accepted a position as part of the faculty at Harvard,” says Muldrow in an interview. “It’s a profound opportunity and it shows the caliber of the talent we attracted.”
Former school board member TJ Mertz, who lost his seat in April, says he believes the next superintendent’s biggest challenge will be establishing trust.
“Trust between the community and the district. Trust between the district [administrators] and staff. Trust among staff. Trust between parents and schools,” says Mertz. “Without trust, things don’t work.”
Mertz thinks the school board should hire an interim superintendent who is a caretaker — someone who will stay on only until a permanent replacement is hired. “Interims have a habit of becoming the next superintendent if they are applying to fill the position permanently. The last two interims in the Milwaukee school district become superintendents,” says Mertz. “It creates a real awkwardness around a search. It’s awkward to be simultaneously vetting and working with someone.”
M Adams, co-executive director of Freedom Inc., hopes the search process will be inclusive.
“We want community members — not just the standard people who typically hire superintendents — to have a real influence over the process,” says Adams. “Madison really struggles with the issue of intention versus impact…. Unless we do something radically different, it doesn’t matter what any superintendent does or doesn’t say, nothing will change.”
David Blaska, who lost to Muldrow in one of the races for school board this spring, criticizes Cheatham for caring too much about “identity politics.”
“I am surprised [by Cheatham’s resignation] because she is so in sync with the new school board members — who are three radical leftists,” says Blaska, who adds he doesn’t anticipate much changing with a new superintendent. “The school board wants more of the same so that’s what I imagine they’ll go and get.”
Blaska says if it were up to him, he’d hire Kaleem Caire, founder and CEO of One City Schools.
Caire, who also ran for school board this year and lost to Cris Carusi, didn’t always agree with Cheatham. But he says she did a great job.
“She had to get everybody on the same page about how they were going to address the achievements of our students,” he says. “I think she did a good job of bringing everybody together around a single mission. She stayed six years, that’s longer than most superintendents.”
Caire also praises Cheatham for making black excellence a priority. “Given the long history of underachievement among that population, for her to make that a focus of the Strategic Framework was huge,” he says.
He also has high expectations for her replacement. “I hope that we have a person of color, finally, leading the district,” he says. “It’s not about identity politics; it’s about really being able to connect the dots.”
Cheatham grew up in the Chicago suburbs, but hoped to one day teach in the inner city, according to an October 2013 Isthmus profile. After graduating from the University of Michigan, she instead went to California, which was experiencing a teacher shortage at the time. She taught eighth grade language arts at a district south of San Francisco from 1997 to 2003. After several other stops, she was back in Chicago in 2009 and working for the public schools as the chief area officer or “mini-superintendent,” overseeing 25 schools. In 2011 she became chief of instruction.
When Cheatham first got to Madison she visited every school in the city in an effort to see the district firsthand. She also organized community listening sessions to hear from staff, students and parents. Her takeaway from those meetings was that the district had potential. “It’s not a broken school system, which is different from what I’ve experienced in places like Chicago,” she said. “We’re not a district in crisis.”
She would soon roll out her first Strategic Framework to address the challenges facing the district, including its wide racial disparities around achievement.
At the time, she told Isthmus that she hoped this would be her family’s last stop for a while. “I believe this deeply, as does my husband, that this is a place we can really envision putting down roots and raising our family,” she said.
