Wikipedia Deep Dive

Janice K. Jackson

14 min read

From a Two-Bedroom Apartment to Running America's Third-Largest School District

Before Janice Jackson became the most powerful person in Chicago education, she was folding clothes and running a cash register at an Express store. The retail chain, known for its affordable business-casual attire, was where Jackson worked while waiting for her first teaching job to come through. Within two decades, she would be making decisions that affected 340,000 students across nearly 600 schools.

That trajectory—from cashier to superintendent—tells you something important about Jackson's story. It's not the narrative of an education reformer parachuting in from the Ivy League with theories about how schools should work. It's the story of someone who grew up in the system, taught in the system, and eventually led the system.

Growing Up on the South Side

Jackson was born on May 22, 1977, at Englewood Hospital on Chicago's South Side. She was the third of five children in a working-class family. Her father drove a taxi. Picture this: seven people—two parents and five kids—sharing a two-bedroom apartment in the Auburn Gresham neighborhood.

Auburn Gresham sits in the southwestern part of Chicago, a predominantly Black community that has faced its share of economic challenges over the decades. When Jackson was growing up there in the 1980s and early 1990s, it was the kind of neighborhood where resources were tight but community ties ran deep.

She attended Cook Elementary School in the neighborhood, then Hyde Park Career Academy for high school. Hyde Park, located in the South Side neighborhood of the same name, focused on preparing students for careers—a more vocational approach than the traditional academic track. Jackson graduated in 1995 and stayed local for college, attending Chicago State University on the far South Side.

Chicago State is worth understanding. It's the city's only four-year public university that's majority Black, historically serving students who might be the first in their families to attend college. The school has faced funding crises and enrollment challenges over the years, but it has produced generations of teachers, social workers, and professionals who went on to serve their communities. Jackson graduated in December 1999 with a bachelor's degree in history and secondary education.

The Making of an Educator

Jackson's first teaching job was at South Shore Community Academy High School, a Chicago Public Schools institution on the southeastern edge of the city, near Lake Michigan. She taught social studies—which in American high schools typically means some combination of history, government, economics, and geography.

But she didn't stop there. While teaching full-time, Jackson returned to Chicago State to pursue a master's degree in history. This kind of continuous education would become a pattern throughout her career. She was always studying, always adding credentials, always preparing for the next thing even while doing the current thing.

The next thing came in 2003, when Jackson got involved in designing a brand-new school from scratch.

Building Al Raby High School

The early 2000s were an interesting time for education reform in America. The Bill and Melinda Gates Foundation—funded by the Microsoft co-founder's enormous wealth—was pouring money into what was called the "small schools movement." The theory was straightforward: large, anonymous high schools with thousands of students weren't working, especially for poor and minority students. Smaller schools, with maybe 400 students instead of 2,000, could provide more personalized attention and keep kids from falling through the cracks.

Jackson helped secure a $500,000 grant from the Gates Foundation to create Al Raby High School, named after Albert Raby, a Chicago civil rights activist who had worked alongside Martin Luther King Jr. during the 1960s open housing marches.

The school opened in 2004 in a previously closed Chicago Public Schools building near the Garfield Park Conservatory. This is a detail worth pausing on: Chicago has been closing schools for decades, a consequence of population loss as residents moved to the suburbs or the Sun Belt. These closures hit Black neighborhoods particularly hard, leaving behind empty buildings that became symbols of disinvestment. Repurposing one of these buildings for a new, innovative school carried symbolic weight.

Al Raby High School focused on technology, science, and environmental studies. It kept enrollment under 400 students—small enough that teachers could know every kid by name. The results were notable: the school achieved one of the lowest dropout rates in the city.

Jackson hadn't planned to run the school. She later said she originally intended just to help design it. But when it opened, she was only 27 years old and serving as principal. She would stay in that role for years while simultaneously pursuing a second master's degree—this one in educational leadership and administration from the University of Illinois at Chicago—and then a doctorate in urban education leadership from the same institution.

Her mentor during the doctoral program was Steve Tozer, who directed the urban education leadership initiative. Tozer's program was specifically designed to train school leaders for the unique challenges of large, diverse urban districts. During these years of intense study, Jackson and her partner Torrence Price, whom she had met in 2005, had a daughter together.

Rising Through the Ranks

Arne Duncan, who served as CEO of Chicago Public Schools before becoming President Obama's Secretary of Education, noticed Jackson. He tapped her to create another new school: George Westinghouse College Prep, named after the industrialist and inventor who founded the Westinghouse Electric Company. She became that school's principal as well.

In 2014, Jackson moved from running individual schools to overseeing many of them. Chicago Public Schools divided the city into thirteen "networks," each supervised by a chief who reported to the central administration. Jackson became one of these network chiefs, responsible for 26 schools serving 14,000 students.

The following year, she was elevated to chief education officer—essentially the number-two position in the district, overseeing academic programs and school quality. Her boss was Forrest Claypool, a longtime Chicago political operative whom Mayor Rahm Emanuel had installed as CEO. By various accounts, Jackson and Claypool had a tense relationship. They "did not see eye-to-eye," as one observer put it.

That tension would soon become irrelevant.

The Path to the Top Job

On December 8, 2017, Forrest Claypool resigned as CEO of Chicago Public Schools. He was the second consecutive CEO to leave under a cloud. His predecessor, Barbara Byrd-Bennett, had actually gone to federal prison for steering a no-bid contract to a company that had agreed to pay her kickbacks. Claypool's departure involved ethics violations related to covering up a fraud investigation.

The Chicago Board of Education—the seven-member body that officially governed the school district, though its members were all appointed by the mayor—named Jackson as interim CEO. Soon after, they made her permanent.

This was historically significant. Jackson was the first head of Chicago Public Schools in twenty years who had actually worked as a teacher and principal in the district. Her predecessors had been lawyers, businesspeople, and political figures. She knew what it was like to stand in front of a classroom full of teenagers.

Inheriting a District in Crisis

Jackson took over a school system facing challenges on multiple fronts.

Enrollment was declining. This is a problem that has plagued many urban school districts as families move to suburbs or send their children to charter schools or private schools. Fewer students means less funding, since school districts receive money based on how many students they serve. It also means difficult decisions about which schools to close or consolidate.

But the enrollment picture was uneven. Some schools were overcrowded, with students crammed into hallways and temporary buildings. Others were half-empty, operating inefficiently with more staff than students required.

The district's special education program was under state scrutiny. The Illinois State Board of Education had placed a monitor on the program after discovering that Chicago Public Schools had been improperly delaying or denying services to students with disabilities. Under federal law, schools must provide "free and appropriate public education" to students with disabilities, including services like speech therapy, occupational therapy, and specialized instruction. Failing to do so isn't just harmful to children—it can result in expensive lawsuits and loss of federal funding.

Jackson also inherited the reputational damage from the scandals that had taken down her predecessors. And just before she took office, the district had announced several school closings, always a contentious issue in a city where closed schools meant lost community anchors.

Building Something New

Jackson moved quickly to put her stamp on the district.

She created the Great Expectations mentoring program, which aimed to encourage Black and Latino men to pursue leadership positions in Chicago Public Schools. This addressed a persistent gap: while the student body was overwhelmingly minority, the leadership ranks were not. Having administrators who looked like the students they served wasn't just symbolically important—research suggests it can improve outcomes, particularly for students of color.

In 2018, she established an Office of Equity, making Chicago the largest city in America whose school district had a dedicated equity office. The concept of equity in education goes beyond simple equality. Equality means giving everyone the same resources; equity means giving each student what they need to succeed, recognizing that students start from different places and face different obstacles.

Education Week, a national publication that covers K-12 education, recognized Jackson as one of their "Leaders to Learn From" in early 2018.

The Sexual Abuse Crisis

On June 1, 2018, the Chicago Tribune published an investigation that would define Jackson's tenure more than any of her initiatives.

The newspaper's reporters had documented over a decade of mishandled sexual abuse cases in Chicago Public Schools. Students had been assaulted by teachers, staff, and other students. Adults who should have protected children had instead covered up allegations, failed to report them to police, or allowed accused employees to quietly resign and move on to other jobs—sometimes at other schools.

The scope was staggering. This wasn't a few isolated incidents. It was a systemic failure.

Jackson's response was extensive. She published a four-page action plan and distributed it to every employee in the district. She committed $500,000 to fund a comprehensive external review led by Maggie Hickey, a former federal prosecutor and former inspector general for the state of Illinois. She brought in the law firm Schiff Hardin to assist.

She ordered fingerprinting and background checks for all employees before the next school year. She changed policy so that employees accused of misconduct by students would be barred from school buildings while investigations were ongoing—previously, accused employees could continue working, potentially in contact with the students who had accused them. She expanded the definitions of inappropriate conduct in district policies. She created a new Office of Student Protections and Title IX to specifically handle cases of sexual misconduct between students.

Title IX is the federal law that prohibits sex discrimination in educational institutions that receive federal funding. While most famous for its impact on women's athletics, it also covers sexual harassment and assault in schools.

Despite all this, Jackson faced criticism. Some felt her response was too slow or insufficiently forceful. She was also criticized for failing to attend meetings of the Illinois State Board of Education and Chicago City Council where the crisis was being discussed. Whether those absences reflected poor judgment, scheduling conflicts, or strategic avoidance became a matter of debate.

Mayoral Politics

In Chicago, the mayor controls the public schools. Unlike most American cities, where school boards are elected by voters, Chicago's school board was appointed entirely by the mayor. This meant that every new mayor could replace the CEO of Chicago Public Schools if they chose.

In 2019, a new mayor was coming. Rahm Emanuel, who had dominated Chicago politics for eight years, announced he would not seek a third term. The sexual abuse scandal had damaged his administration, and other controversies—most notably the police shooting of Laquan McDonald, a Black teenager, and the city's handling of the resulting video—had made his position untenable.

The mayoral race quickly became about Jackson.

During the runoff election between Toni Preckwinkle, the Cook County Board President, and Lori Lightfoot, a former federal prosecutor, both candidates were asked whether Jackson should keep her job.

Preckwinkle offered her support.

Lightfoot was sharper. She called the sexual abuse scandal "the epic failure of leadership by Rahm Emanuel and Janice Jackson." But she stopped short of committing to fire Jackson. "I'm willing to hear her out," Lightfoot said, "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."

Jackson offered to meet with both candidates. Four days before the election—by which point polls showed Lightfoot was likely to win—Jackson met with her at the Boyce Building, a historic structure that houses the Chicago Teachers Union offices and other education-related organizations.

Whatever happened in that meeting, it worked. After Lightfoot won the election in a landslide and took office in May 2019, she announced that Jackson would stay on, at least temporarily. On June 3, she made it permanent.

Teachers' Strikes and Pandemic

In October 2019, the Chicago Teachers Union went on strike. This was the second major strike in seven years—the first had occurred under Rahm Emanuel in 2012—and it lasted eleven school days.

Jackson's relationship with the union was complicated. She had publicly criticized the Chicago Teachers Union for being "overly political," a charge that resonated with some parents and reform advocates but inflamed labor supporters. The union, for its part, represented the teachers who had once been Jackson's colleagues. The strike ended with a deal that included smaller class sizes, more support staff, and raises for teachers—though not everything the union had demanded.

Then came COVID-19.

The pandemic that began in early 2020 upended every school district in America, but it hit urban districts serving poor and minority students especially hard. Chicago Public Schools, like districts everywhere, shifted to remote learning. The challenges were immense: ensuring every student had a computer and internet access, training teachers to use new technology, keeping students engaged through a screen, providing meals that many students depended on.

The pandemic dominated the last two years of Jackson's tenure. Debates over when and how to reopen schools became intensely political, with the teachers' union often at odds with the administration over safety protocols.

Departure and Legacy

In May 2021, Jackson announced she would step down as CEO on June 30. Her departure ended a 22-year career in Chicago Public Schools—from that first teaching job at South Shore to the superintendent's office.

Mayor Lightfoot praised Jackson's leadership. So did Miguel del Valle, the president of the Chicago Board of Education. The woman who had nearly been fired before she even got a chance to prove herself to Lightfoot was leaving with accolades from the same mayor.

In September 2021, Jackson announced her next role: CEO of HOPE Chicago, a scholarship program that helps Chicago students afford higher education. The program, funded by philanthropist Pete Kadens, covers tuition and provides coaching and support services to help students actually graduate—recognizing that money alone isn't enough for students who might be the first in their families to navigate college.

What Comes Next?

When Jackson's name surfaced as a potential candidate for the 2023 Chicago mayoral race, she declined, saying she had no interest in the office.

But political observers haven't stopped speculating. The 2027 mayoral election, if current Mayor Brandon Johnson doesn't seek or win reelection, could bring Jackson's name back into circulation. She has the experience, the connections, and a story that resonates in a city where many people grew up in circumstances similar to hers.

In 2024, Jackson signed an open letter opposing Mayor Johnson's decision to fire Pedro Martinez, her successor as CEO of Chicago Public Schools. The letter positioned her, once again, at the center of Chicago education politics—even from outside the system.

She married Torrence Price in 2017, the same year she became superintendent. Their daughter, born while Jackson was still working on her doctorate and running Al Raby High School, has watched her mother's career unfold from inside the Chicago Public Schools system—first as a student, then as the child of its leader.

From a two-bedroom apartment in Auburn Gresham to the halls of power in downtown Chicago, Janice Jackson's story is, in many ways, the story of what Chicago's public schools are supposed to make possible. Whether the system she led for nearly four years can deliver similar opportunities to the 340,000 students it serves today remains the question that will ultimately define her legacy.