When Mayor Lori Lightfoot offers someone the job of running Chicago Public Schools, she will try to sell it as an opportunity to bring “transformative change to our public education system,” as she put it on Monday.

But in reality, the next chief executive officer of the nation’s third largest school district will be walking into a complex, difficult job at a precarious time. Even CEO Janice Jackson, who called it her “dream job,” is stepping away this summer after three years at the helm.

For one, there is no guarantee that Lightfoot will be reelected mayor in two years. As Lightfoot campaigns, the next CEO will have to navigate a highly politicalized election season in which the head of CPS will be under the microscope. Making any big changes during this time likely will be difficult.

And then if Lightfoot loses, a new mayor may want to bring in his or her own team to take over.

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Michael Casserly, executive director of the Council of the Great City Schools, said he thinks the top job in Chicago Public Schools would appeal to many candidates. He points out Chicago is an attractive city and that the school district has made a lot of academic gains in recent years.

But the fact that the mayor’s term is up in two short years will be a “big consideration” for candidates, he said.

The school district also may be taken out of the mayor’s control altogether, as momentum is building behind a bill that would eventually create an elected school board in Chicago. It’s currently appointed by the mayor. While many details of a final bill are still unclear, an elected board would likely be given the power to hire its own school district leader.

Stuck in the middle

On top of the possible temporary nature of the job, the next CEO will have to find a way to work with both the mayor and the Chicago Teachers Union, both of which can be challenging.

Outgoing CEO Janice Jackson found herself in the middle of what became a toxic relationship between the mayor and the teachers union. At the press conference announcing her resignation Monday, Jackson called the politics in education in Chicago “ugly” and an “outlier.” 

She admitted that she’s worn out from the fighting between the school district and the teachers union. Under her watch, the union went on strike once and came close several other times.

Of the union, she said “the tactics they use, I don’t agree with and they make it very difficult for good people to do these jobs.”

Gov. JB Pritzker also recently signed a bill expanding the union’s bargaining rights, which could force the school district to negotiate more with the union and potentially face more labor unrest.

Jackson, who will leave on June 30, also had to manage the mayor, who is notoriously difficult to work for. Jackson said she and the mayor developed a friendship over time and said she doesn’t think the mayor gets enough credit for work she’s done for CPS. But others inside CPS say that Jackson never felt supported by Lightfoot in the same way she was supported by former Mayor Rahm Emanuel, who appointed her to the job in 2018.

In the Chicago Teachers Union statement on Jackson’s departure, the union pointed to the mayor as an obstacle for the next school district leader. Union leaders have publicly noted tensions during contract negotiations between the mayor and school district officials.

“We are hopeful the mayor can improve on her ability to work collaboratively and cohesively with others, in particular her own staff and appointees in CPS,” the CTU statement reads.

While the union wished Jackson and two other departing top leaders “the best in their future endeavors,” it did not apologize for making their tenure difficult or indicate that they will back down in the future.

Along with Jackson, Chief Operating Officer Arnie Rivera and Chief Education Officer LaTanya McDade also recently announced they are leaving the district.

Pandemic effects

The next CEO also will be taking over at a time when the academic progress made over the past decade could be challenged. Jackson touted test scores growing at faster rates than anywhere else in the country and increasing graduation and college enrollment rates.

But Jackson and Chief Education Officer McDade sounded alarms this fall as they saw attendance and grades plummet while children were at home learning remotely during the pandemic.

“I worry that unless we act with urgency, we will lose a generation of students,” McDade told the Board of Education last fall. Jackson said the situation made her desperate to get students back into classrooms, learning in person.

They managed to eventually open schools, but most students are still remote. No one knows the lasting impact of the pandemic on academic achievement, but national research is predicting learning gaps, especially for low-income students and students of color. The next CEO will have to figure out how to counter any backsliding.

CPS’ new leader also will have to manage a windfall of $1.8 billion from the federal government. It’s to be used, in part, to mitigate learning loss. Jackson has said that before she leaves she plans to lay out a comprehensive framework for how this money will be spent.

But she won’t be around for the fight over it. Already, parent and community groups, as well as the Chicago Teachers Union, have said they want to have a say in how this money is spent.

And while advocates have said they don’t want to see the bulk of it spent on repaying debt, the school district is weighted down with it. At the end of the last fiscal year, the school district had about $8.1 billion in outstanding long-term debt and $500 million in outstanding short-term debt.

A shrinking school district

The pandemic also has exacerbated some long-standing, troubling trends in Chicago Public Schools, and the next CEO needs to be ready to deal with them.

The most critical is a loss of students. In the two decades prior to the pandemic, the school system was down more than 80,000 students. Then, this year, enrollment dropped by another 15,000, though some of those students could return next year.

As of this school year, 103 schools now have fewer than 250 students; up from 63 when Jackson took over. Some of these schools might rebound once classes are normal next year, but many of them had dwindling populations before the pandemic.

Because schools are funded based on enrollment, many of these schools struggle to offer robust programming. Jackson has provided many of them extra grants, but that makes them expensive to run. They include charter schools and once-vibrant neighborhood high schools that aren’t attracting students.

Lightfoot and Jackson have shied away from closing schools. But they also have not presented a comprehensive strategy for dealing with under-enrolled buildings.

The next CEO will inherit the hard questions of what to do with these schools in a way that takes into account communities, the budget and, most importantly, the quality of education for the students who attend them.

Sarah Karp covers education for WBEZ. Follow her on Twitter @WBEZeducation and @sskedreporter.