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The Education of Janice Jackson

The high-profile chief of Chicago Public Schools inherited a system in crisis. Now she’s learning just how hard it is to fix it.

Above:Scenes from a July day in Jackson’s life — in her downtown office and at a freshman orientation at Wendell Phillips Academy in Bronzeville.

In white Adidas sneakers with black stripes instead of her usual three-and-a-half-inch heels, Janice Jackson strides purposefully through the unfinished school’s empty hallways, stepping deftly over extension cords and around banks of soon-to-be-installed orange and blue lockers. The sound of beeping forklifts drifts in from outside. As we walk past a double staircase inside the main entrance, the 42-year-old Chicago Public Schools chief explains that the foyer will be decorated with art that references the history of the neighborhood. Down the hall, she shows me the room slated to house a health center that can be used by both students and community residents. Then we head upstairs to the library.

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“Oh,” Jackson says, drawing a sharp breath as we enter the room. At first, it’s hard to read her reaction, but it quickly becomes apparent it’s one of wonder. Though still empty, with cardboard covering the floor, the space feels full of possibilities. Half of the room is soaringly open, thanks to two-story windows framing the sky; the other half, with a lower ceiling and dark blue walls, has a Zen retreat vibe. Sleek circular pendant light fixtures hover above us at varying heights. Her eyes panning the room, Jackson says, “I’m thinking of what this could mean to a student from this neighborhood.”

Englewood STEM High School, which welcomes its inaugural freshman class in September, is an $85 million investment in a neighborhood where nearly half the residents live below the poverty line and more than 90 percent of students commute to schools outside the area. But for Jackson — a former CPS student and teacher who by her own account was born to the CEO job — it’s more than that. It’s a gleaming emblem of what she believes to be the singular goal of her tenure: bringing equity to a school district where the best educational opportunities have long been concentrated in white neighborhoods. In Jackson’s eyes, achieving that goal starts with restoring trust in a broken system. “I have to convince people, especially marginalized people, that this is for them, too,” she says.

It won’t be easy. Having taken the CEO job in December 2017 in the wake of a string of scandals and the announcement of school closings — including four CPS high schools in Englewood — Jackson soon had to weather new setbacks, as well as a seismic shakeup in City Hall, while also facing down angry residents so accustomed to loss that many had given up on the district completely. “You think they’re putting all this new stuff in here for us?” says Bobbie Brown, the local school council chair for one of Englewood’s high schools, Harper, which has been allowed to remain open only until its remaining students graduate. “No. They treat our children like cattle.”

Jackson at Wendell Phillips Academy in Bronzeville
“This hasn’t been a honeymoon,” says Jackson, here at Phillips Academy.

Brown’s comments echo those of many residents who suspect the new school will be a magnet or special-track school for outsiders, despite Jackson’s assurances to the contrary. Others questioned why the $85 million couldn’t have been poured into the existing schools or why three years of students being displaced couldn’t have been avoided by consolidating the kids in one of the older schools.

“We don’t have to relive that time,” says Jackson when I ask about the pushback against the closings and the new school. “They had legitimate concerns and we needed to discuss them with the community.”

It’s a typically shrewd seeing-both-sides response from a public figure managing a fracas. When I press her further, she fans herself and chuckles dryly. “Just know I was called every name under the sun. I saw the faces. I understood. No one believed a state-of-the-art facility would be built here or that it would be for them. But if name-calling bothers you, this isn’t the job for you. I talk to aspiring women leaders all the time, and I tell them, ‘You better get comfortable with being called a bitch.’ ”

 
As a 10th grader at Hyde Park Career Academy
As a 10th grader at Hyde Park Career Academy Photo: Courtesy of Janice Jackson

Thirty-two years ago, Ronald Reagan’s education secretary, William Bennett, famously called Chicago’s public schools the worst in the nation. He deemed them unsalvageable and urged parents to send their kids to private schools so that the entire system could be shut down. At the time, Jackson was in fifth grade on the South Side, where she and her parents and four siblings shared a two-bedroom apartment in Auburn Gresham, and she remembers the moment. She also remembers watching Sweet Valley High on TV as a teenager, marveling at the differences between the fictional school and the one she attended, Hyde Park Career Academy (now Hyde Park Academy). Where was the leafy campus? The comfy-looking library? The pristine classroom? “I got a good education, but I always felt like my schooling was less than what it should have been,” she says.

We are seated in Jackson’s corner office at CPS headquarters downtown. The room is light and airy, with white walls and a wide bank of windows. Dressed in a floaty white blouse, paisley pants, and a Zara belt, Jackson had gotten up from her desk when I was shown in and invited me to join her at a small round table. The drink of the day is water.

Once our conversation gets underway, I’m surprised to note a total absence of interruptions — no knocks on the door from aides, no apologies for having to take a call or return a text. Jackson exudes an air of control and calm precision. She speaks in paragraphs. Her knowledge is deep and extends well beyond public education. She maintains eye contact as she talks, breaking her gaze only to stare into the middle distance as she’s finishing a particularly complex thought.

When at one point I cast my eyes across the smattering of family photos and awards behind her desk, the room’s only personal touches to speak of, Jackson admits she hasn’t had time to make the office her own. “I did not pick this green carpet, and I did not paint that accent wall yellow,” she says. Admittedly, she’s been busy. “This hasn’t been a honeymoon.”

Indeed, Jackson has inherited major problems: declining enrollment, schools that are drastically over- or underpopulated, the Illinois State Board of Education imposing a monitor on the district’s special education program after finding that CPS had delayed and denied some services to students, plus an investigative report by the Chicago Tribune that showed CPS had mishandled sexual abuse cases for over a decade. What’s more, her two predecessors left under a cloud of scandal — one of them is in federal prison for taking kickbacks. Jackson is the district’s seventh CEO in 10 years.

As a student teacher at Morgan Park High School in 1999
As a student teacher at Morgan Park High School in 1999 Photo: Courtesy of Janice Jackson

She is also one the first in decades who is an educator. Jackson started teaching social studies at South Shore High School in 1999, while earning a master’s in education at Chicago State University. “At the time, South Shore was one of the lowest-performing schools in the state.” Jackson remembers stuffing student papers in her backpack to grade at home and being told by another teacher to forget it — that if she couldn’t get something done during work hours, not to bother.

It was as if William Bennett’s assessment had become self-fulfilling. “I didn’t like these approaches that said, ‘The kids live in poverty so we shouldn’t have standards.’ Until then, I hadn’t realized that so many black people were having a different experience in education than I had had. I started feeling I should be in CPS [leadership], that I had gifts and the courage to try to do something.”

In 2003, when she was just 26, she helped secure a $500,000 grant from the Bill & Melinda Gates Foundation to underwrite the opening of Al Raby High School in East Garfield Park. Occupying a closed CPS building that had once housed a girls’ high school, the new school focused on intensive support for a small group of fewer than 400 students, with an emphasis on science, technology, and the environment. The school was next to the Garfield Park Conservatory, and Jackson was able to create a partnership with it on various projects. The following year, Jackson was made principal. “At the time,” she says, “the area had the highest murder rate in the city. But those kids in that school achieved so much because the teachers there believed they could and we told them they could.”

By then, Jackson was already enrolled at the University of Illinois at Chicago, where she’d just earned another master’s and would go on to earn a doctorate, while continuing to work as a principal. “In her admissions material, Janice wrote that her long-term goal was to be the CEO of CPS,” recalls Steve Tozer, who was the founding director of UIC’s Center for Urban Education Leadership and a mentor to Jackson. “No other graduate student has ever written that.”

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Longtime friends say they saw signs of intense ambition even earlier. “She wanted a career where she accomplished something important,” says Lakesha Wilson-Hill, a former high school classmate who is now an accountant and is still close to Jackson. “She wanted to travel to Europe, she wanted experiences.”

Jackson credits her father, a cabdriver, with giving her the desire to broaden her horizons, encouraging her and her siblings to follow current events in both the city and beyond and express well-reasoned opinions. “My father was very protective — no staying over at other kids’ houses and things like that — but he also wanted us to know the world,” she says. “He wanted us to think our way through things.”

Another friend, Yasmin Curtis, recalls that even as a teenager hanging out at the Evergreen Plaza shopping center, Jackson displayed a calculated sense of self-presentation. She didn’t have much money for clothes, so she concentrated on crisp white shirts, ironed to perfection, and she began to develop her well-known penchant for heels. “I tell her even now, ‘I’m going to buy you a nice pair of adult flats,’ ” says Curtis, “but she won’t hear of it.” (Jackson confirms this: “She bought me flats for my birthday,” she says, affecting indignation. “Can you believe it?”)

 
At a 2018 Chicago Board of Education meeting addressing revelations of rampant sexual assault and abuse of students
At a 2018 Chicago Board of Education meeting addressing revelations of rampant sexual assault and abuse of students Photo: Brian Cassella/Chicago Tribune

Jackson joined the ranks of CPS management in 2014, first as a community-network chief and then as chief education officer, a role that thrust her into the public eye. During the tenure of her predecessor in the CEO’s office, Forrest Claypool — who took over after Barbara Byrd-Bennett resigned following her indictment in the kickback scheme that would send her to prison — the inside joke at CPS was that, in photos, Jackson increasingly had the blank stare of someone being held against her will. There she is in a news clipping from 2016, standing just behind Claypool, a wooden expression on her face, as he announces a contract deal with the Chicago Teachers Union. And there she is again the following year, same expression, behind Mayor Rahm Emanuel as he holds a City Hall press conference to announce that the school year would not be cut short, despite a funding shortfall.

Jackson made no secret to those who knew her of how unhappy she was with many decisions — including the closing of 50 schools on the South and West Sides — the district was making under Byrd-Bennett and Claypool, a local pol and Emanuel ally with no experience in the educational system. In December 2017, when Claypool resigned, accused of lying to undermine an ethics investigation into improperly awarded contracts, and Jackson was appointed interim CEO, her expression sank from wooden to dour. “I was angry,” she says of that moment. “Yes, I’ve always wanted to be CEO, but not this way. The way he had to leave, it was a black eye for the district. And it hadn’t been that long since the last black eye.”

By January, Jackson had dropped “interim” from her title. Then, less than six months later, everything exploded. Published on June 1, the Tribune’s massive exposé on CPS, titled “Betrayed,” detailed some 500 police reports of sexual assault or abuse inside city schools over the past decade. Students, the article said, had been victimized — sometimes repeatedly — by lunchroom aides, counselors, coaches, award-winning teachers, even two deans. In addition, CPS had run ineffective background checks that exposed students to people with criminal backgrounds, and the district had failed to publicly disclose that past employees had resigned after investigations found credible evidence of abuse and harassment. To make matters worse, the state teacher licensing board often took years to suspend or revoke the licenses of those who’d committed sexual misconduct. One high school girl said she had been assaulted 40 times. Another said that when she was interviewed by an investigator from the CPS law department, he asked what she had been wearing when the abuse took place.

Publicly, Jackson said she “was sick to her stomach” about the revelations, and she tells me she’s still haunted by the details of the police reports. “I see all the high-level cases. And I am a strong person. But they are bad. I dream about them. I wake up about them. It’s disturbing.”

Jackson’s first move was issuing a four-page plan of action that went to CPS employees. She earmarked $500,000 of the district’s budget for a top-to-bottom review, headed by former assistant U.S. attorney and Illinois executive inspector general Maggie Hickey and the law firm Schiff Hardin. Every employee who would be entering Chicago schools in the fall — teachers, aides, coaches, service staffers — now had to report for fingerprinting and a background check. Procedures for responding to and investigating complaints were overhauled. Previously, if a student alleged that an employee did something wrong, the accused would be allowed to stay in the school building while an investigation was conducted. No longer. And the district established a new office to deal with student-on-student sexual harassment and abuse — another central aspect of the Tribune investigation — and created more rigorous definitions of inappropriate behavior.

Still, not everyone felt Jackson was doing enough. When she didn’t show up for an Illinois State Board of Education public meeting about the revelations that summer, even though a seat had been reserved for her, or at a City Council meeting about the scandal six months later, critics pounced. “Where was the boss on Wednesday?” asked the Sun-Times’ editorial page after the City Hall meeting. “As a symbol of CPS’s commitment to resolving the matter,” the editorial read, “Jackson should have been sitting front and center in the Council chambers. Demonstrating leadership just by showing up is no small thing.” Jennie Biggs, the communications and outreach director for the advocacy group Raise Your Hand, says, “I don’t blame Janice for the scandal, but it was very disappointing when she didn’t attend the state and City Council meetings. Extremely disappointing.” (Asked about the no-shows, Jackson’s director of media communications says that after numerous media interviews, a virtual town hall with staff, and “countless stakeholder meetings,” the CEO “felt comfortable entrusting her team of district leaders to participate in the hearings on her behalf.”)

What Jackson found hardest to deal with about the sex abuse scandal, though, was not her public critics but her private fears. The sheer scope of the abuse made her more acutely aware of potential harm in the world around her, she says — and around her 10-year-old daughter and 13-year-old stepson. “I was out with my kids, and I said to my son, ‘Watch your sister.’ ”

 
With her husband, stepson, and daughter on a family trip in April
With her husband, stepson, and daughter on a family trip in April Photo: Courtesy of Janice Jackson

Longtime friends describe Jackson as honest and direct, sometimes disarmingly so, and not inclined to shy away from touchy subjects. In my encounters with her, she demurs only once, and then only momentarily: when I bring up the subject of her brother Cordney. “Talking about this can break me down,” she says, her words catching in her throat. After taking a breath and collecting herself, she says, “My brother was an amazing, smart person. I used to say he was like a black Cliff Clavin from Cheers, because he knew all the most obscure facts, random factoids. He was generous. He loved sports. He loved competition. He would watch two rats race across the street just to see which one won. He died protecting my mom. That’s just who he was. But I wish he had not intervened.”

Jackson is speaking of the evening, in 2010, when two men, with ski masks over their faces, broke into Jackson’s parents’ house in West Pullman — a home she had bought them a few years earlier — and robbed her mother and a group of her friends who’d come over for a weekly card game. When Cordney tried to defend the women, one of the intruders fatally shot him. He was 31. The crime remains unsolved, and the family rarely discusses it. Jackson’s mother is raising Cordney’s son, now 15.

Cordney’s death changed Jackson. She stopped postponing things. She says she felt freer and more determined to do what she wanted, because time might be limited. And the tragedy strengthened her faith in education. “It gives people an opportunity,” she says, “and lessens the chance they will do violent things.”

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At her home in Bronzeville, Jackson and her husband, a construction worker named Torrence Price, value family stability, keeping social engagements to a minimum. Partly this is out of necessity, given the demands of Jackson’s job. “I can’t take my kids to school in the morning anymore. That bothers me.” Her heightened visibility has also eroded her anonymity. Jackson was in a restaurant recently with her family. “A man at the next table was holding up his phone for his wife to look at my picture,” she recalls. “He’s saying, ‘See, it’s her.’ And I felt self-conscious. I thought, Can I order a drink now? Are my kids eating good food so I don’t look bad?”

Her family has done their best to adjust. Over the past two years, Price has had to learn how to cook. “On a skill level of 1 to 10 — well, he’d tell you something else, but he’s about a 6. And he’s progressing.” Sometimes Jackson will walk him through dinner prep via FaceTime from her office.

The two met at a bowling alley in 2005, introduced by a mutual friend. “He’d give you some TV version of a romantic story, but it wasn’t like that at first. My friend called me up later and asked me to go out with him just one time. So I did. And he is so funny and kind and he is not intimidated by me.” Over time, Jackson’s mother pointed out that Price was the first person Jackson would call with good news, and the first person she’d call with bad news, too.

The two got married in 2017. “Despite the fact that he hasn’t worked in this environment, and he didn’t go to college, he gives me good advice. Because he understands people, and he tells me the truth.”

 

The fallout from the sex abuse scandal was still thick in the air when, just as the 2018–19 school year was getting underway, Emanuel announced he wouldn’t run for reelection. Overnight, Jackson appeared to be a lame duck. When a new mayor was elected, the thinking ran, the current CPS chief would be out.

During the mayoral campaign, Jackson became a political hot potato. In a televised forum with runoff candidates Toni Preckwinkle and Lori Lightfoot, the opening policy question posed by the moderator was whether Jackson should keep her job. “I was in my kitchen and my husband was in the basement with the sound on the TV turned up loud so I wouldn’t miss the beginning of the debate,” says Jackson. “I remember walking halfway down the stairs and thinking, Am I really the first question?”

Preckwinkle expressed support for Jackson, but Lightfoot was more circumspect, citing “the epic failure of leadership by Rahm Emanuel and Janice Jackson,” adding, “I’m willing to hear her out, but she is going to have to demonstrate to me that she understands she made a mistake and rectify that with the parents and the teachers and the kids.” This statement backed up a previous one Lightfoot had made: that Jackson hadn’t moved quickly enough to fix the problem. A few weeks later, a Tribune editorial noted that the high degree of criticism of Jackson “raised the odds of a departure.”

Jackson offered to meet with both candidates. Four days before the April 2 election, when the outcome looked certain, Lightfoot arranged a meeting in a conference room in the Boyce Building on Dearborn. The implication was that Jackson would need to make a very compelling case to keep her job. Both women brought their chiefs of staff along, but before the meeting started, Jackson asked if she and Lightfoot could talk one on one. “And she was open to that,” says Jackson. “I think she respects people who are as direct as she is.”

Of what transpired at the meeting, Jackson says, “We just launched in. It wasn’t combative. I explained my decision-making to her, and she asked probing questions. She listened to me, and I listened to her.” Jackson admitted to Lightfoot that she was upset by some of the criticism lobbed at her during the campaign. “I disagree that my response was an ‘epic failure.’ I explained that this was a problem so monumental that it deserved more than a piecemeal response. And that takes time. I didn’t go in there and try to BS her. That’s not my style. I didn’t hold back anything, either. We had a real dialogue.”

Gradually, Jackson began to win Lightfoot over. “I knew we had turned a corner when we started talking to each other about our kids.”

After Lightfoot took office in May, she announced that Jackson was staying on. When I sought an explanation from Lightfoot, I received an emailed response: “In our short time together, Dr. Jackson has impressed me both as a passionate advocate for our students, and as a visionary leader for the role of public education in our city. She and her team have rightly received universal praise from families and staff alike for their creativity, energy and dedication, and I look forward to continuing our work together in creating a school system that nurtures our children and inspires them to learn, grow, and thrive.”

Now that the sex abuse scandal and the drama of the election are largely behind Jackson, chronic challenges like regulating charter schools and placating the teachers’ union have returned to center stage. Jackson regards charters with a gimlet eye, having seen how their unchecked spread can cannibalize neighborhood schools in struggling parts of the city. “But I also think school choice is important. We would never question a middle-class family’s choice about where they were going to school. Why would we want to take away a poor family’s choice?”

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As for the teachers’ union, which has said it’s readying for a possible strike in the fall, Jackson insists real progress can be made only if the district secures more money. “I would love to do various things, but we can’t afford to do that unless some rich uncle shows up. So we need to figure out a happy medium. Help me prioritize and help me get there.”

In the meantime, Jackson has been aggressively touting the good things happening in Chicago schools. Graduation rates and most test scores are climbing. Illinois schools will be getting an additional $375 million in state money for their next fiscal year, most of it to be distributed in “tier” funding, meaning the poorly funded systems — namely, Chicago’s — will get a greater share (around $66 million for CPS). The top five Illinois high schools in U.S. News & World Report’s most recent rankings were all Chicago public schools. And a recent Stanford University professor’s analysis of Chicago schools showed that the students in the district are growing academically at a faster rate than those of 96 percent of the public school districts in the country.

But in a district tasked with educating 361,000 students — 89 percent of whom are minorities and 77 percent low income — in one of the most segregated cities in the country, rankings and performance measures tell only part of the story.

 
Janice Jackson

Sixteen years ago, Jackson paid a visit to her friend Lakesha Wilson-Hill in London, where she had gotten a job in an accounting firm. One night, Wilson-Hill invited Jackson to a dinner with two other African American women. Jackson remembers the evening as a pivotal moment in her understanding of the district she would one day lead. “This one woman was going on and on about how terrible her experiences in Chicago schools had been,” says Jackson. “It turned out she had gone to the same school as me. I was in the magnet track and she had been in another track. I hadn’t realized that there could be such disparity in the same system.”

Test-in selective enrollment schools, and selective enrollment and magnet programs within neighborhood schools, have been a hallmark of CPS for years. By imposing income-tiered quotas for magnets and by allowing students to travel to schools outside their own area, CPS has tried to equalize access to the best schools. But those same tactics, combined with the proliferation of charter schools, have had the effect of weakening the open-to-all neighborhood schools that are supposed to be the bedrock of the district. Today less than half of CPS students attend their own neighborhood school.

What’s more, according to a recent interview on the education news site Chalkbeat with Kate Phillippo, a researcher in urban education policy at Loyola University Chicago, students from more affluent families get into their preferred schools far more often than students from less affluent families. This is not surprising, considering that students from well-to-do families tend to be able to afford tutors and test prep courses.

Achieving equity in CPS — which, in the racially driven context of Chicago, essentially means giving nonwhite kids the same access to quality education as white ones — has become something of a crusade for Jackson. Even more so than changing policies around sexual abuse, it is a long-haul endeavor with no easy fixes. She’s impatient with what she calls “chic cocktail or coffeehouse chatter” about equity. “It is impossible to close the current gap between Chicago African American students and their peers in one fell swoop,” she says. “If we did that, people would be in here, investigating every test we administered.”

In her estimation, change has to start on a classroom-by-classroom basis. Jackson has told teachers and principals: “If you walk by a classroom and can recognize that it’s an AP class because it only has a handful of black kids in there, that’s an issue. You have the power to change that. If AP selection is based on teacher recommendations, consider if you are only picking a certain group of kids. Or maybe you’re selecting more males than females. Those are issues we can start to address right away.”

Last year, during a routine meeting, Jackson and members of her staff hatched the idea to create the Office of Equity, now a $1 million line item in the district’s 2018–19 budget. Equity offices are a growing trend among school administrations (check out Oakland, California, or Jefferson County, Kentucky), but now Chicago is the largest city with one. Headed by Maurice Swinney, a former principal at Tilden Career Academy on the South Side, the office is tasked with addressing issues like how the $1 billion earmarked for new school campuses and improvement of existing facilities — announced with fanfare by the Emanuel administration last summer — can be distributed more equitably. (Last year, a WBEZ study showed that some proposed changes skewed significantly toward white schools on the North Side.)

Additionally, Jackson has launched Great Expectations, a mentoring program designed to encourage black men and Hispanic men and women to pursue leadership roles at CPS, where they are significantly underrepresented. (Currently, less than 10 percent of district administrators are black men.) And at the end of March, CPS revealed its five-year plan. Overseen by Jackson and based on input from more than 2,100 parents and community members, 150 business and higher education partners, 5,700 educators and principals, and 2,000 students, it focuses on locking in hard-won academic gains, achieving greater financial stability through better budgetary planning, and, not least of all, restoring the public’s trust in CPS. “If you go back and look at past strategic plans for CPS,” says Jackson, “we did not call out equity as a moral imperative. We do that now.”

For some, Jackson’s words ring hollow. “I have respect for Dr. Jackson as a teacher and as a principal,” says Jitu Brown, a national organizer for the social justice group Journey for Justice Alliance. “But she is not working for the communities as head of CPS. Her job is to bring educational justice to the neighborhoods, not close schools and bring in gentrification.”

Bobbie Brown, the Englewood local school council chair, hasn’t passed judgment yet. “I’m willing to give her a chance, but if she doesn’t do something good, right away quick, she’s got to go.”

In the face of such skepticism, Jackson points to a number. “We now have 1,500 applications for this neighborhood school,” she says of Englewood’s new STEM high school. “There haven’t been 1,500 people saying they want to go to school in Englewood for decades.”

One new school in one struggling neighborhood isn’t going to transform the whole district, but even Jackson’s harshest critics may ultimately have to acknowledge that it’s a start.

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