This story was reported and published in collaboration with WBEZ, the Chicago Sun-Times, and Block Club Chicago, a nonprofit newsroom covering Chicago’s diverse neighborhoods. Stay informed with Chalkbeat Chicago’s newsletter, WBEZ and the Sun-Times’ education newsletter, and Block Club Chicago’s newsletters.
Chicago’s first-ever citywide race for school board president has all the makings of a political drama: millions in campaign contributions, special-interest group endorsements, and a candidate bowing out midstream.
Voters across the city will finalize their pick among four candidates to lead the Chicago Board of Education on Nov. 3. Chicago’s school board president will be directly elected for the first time as more than 30 years of mayoral control ends. The person in this powerful but unpaid position represents the board publicly, runs board meetings, and helps set the agenda. They will work with 20 other members to set a vision and goals for CPS for the next four years.
Former Chicago Teachers Union deputy political director Hilario Dominguez, who graduated from and worked in Chicago Public Schools, is running on a progressive platform that includes expanding preschool to all 3-year-olds and demanding more education money from the state, rather than cutting. The CTU is fueling Dominguez’s candidacy financially as it tries to hold on to control of the school board, which it seized after former union organizer Brandon Johnson became Chicago mayor in 2023.
Jessica Biggs, a former CPS principal and current school board member, wants to prioritize financial stability and high-quality education for every student. She’s backed by the progressive Service Employees International Union Local 73, which represents mostly low-wage Black and Latino CPS workers and is in a bitter dispute with the CTU. She’s also solidified support from the business community and former government officials who worked under former Mayor Rahm Emanuel, including former CPS CEO Janice Jackson and former deputy mayor for education Beth Swanson.
Attorney Victor Henderson, who serves on the board of Urban Prep Charter Academy, is centering his campaign on advancing student achievement and fiscal responsibility. He broke open contribution caps when he lent his campaign $500,000 and has secured support from two Black congress people, prominent lawyers and pastors of large Black South and West Side churches, including Michael Pfleger of St. Sabina and Byron Brazier of Apostolic Church of God.
Leadership consultant Sendhil Revuluri, who served on the school board under former mayor Lori Lightfoot, is promising a focus on student learning and community engagement. He is backed by Chicago Democrats for Education, run by heavyweight political consultant Hugo Jacobo. Jacobo railed against the mayor-appointed board that fired former CPS CEO Pedro Martinez in 2024. Though he says he’s pro-labor, he has advocated for a board that’s independent of the CTU, the powerful union that represents roughly 30,000 teachers and CPS staff and is known for its strong focus on social justice issues.
A fifth candidate, Jennifer Custer, a former educator now serving on the board, dropped out in late August.
All the candidates say they are running because they want CPS to better serve students and families. But they differ broadly in their approaches — Biggs wants to focus on a better-functioning board, Revuluri on holding the district’s top leader more accountable for outcomes, and Henderson on offering an outsider perspective to issues like the budget crisis and charter funding. Dominguez is proposing big initiatives, such as increasing access to youth jobs, paid internships, and mentorships.
Only Dominguez is ruling out closing schools amid the district’s steady enrollment losses, though the others say they would work with communities and move with deliberate care in weighing campus mergers. Henderson would consider opening more privately run charter schools and wants to see them better supported, while the others would further scrutinize existing charters.
The hall leading into Henderson’s downtown office is covered in framed newspaper articles about clients he has represented as a well-known defense attorney: actor Jussie Smollett, who was accused of allegedly faking a racist attack; Ald. William Beavers, who was convicted of tax evasion; the Jackie Robinson West Little League, which was stripped of its U.S. World Series championship title; and a CPS principal who sued after being ousted by her Local School Council.
Henderson is the only candidate in the race who doesn’t have experience as an educator. But the 65-year-old’s four grown children all attended CPS elementary schools in Beverly and selective enrollment high schools.
Henderson is not only a lawyer, but also a former certified public accountant. He says he can read contracts, understand budgets, and take on powerful interests.
“On that board, you need the right combination of people,” he said. “You have to have parents. You have to have principals. You have to have community members, but you also need to have lawyers and maybe doctors.”
Henderson became motivated to run for school board president after he got pulled onto what he calls the recovery board of Urban Prep Academies. At the time, in 2023, the school board was trying to close the charter school network after CPS’ inspector general found “dismal” financial practices, including unaccounted-for spending, taking high-interest loans, and needing cash advances. The founder and former CEO of Urban Prep was recently charged with embezzling more than $100,000 from the organization.
Henderson chalks up Urban Prep’s problems to a bad administration, but says the attempt to shut down the charter network, which serves almost exclusively Black male students, was wrongheaded. Urban Prep officials say they produce better academic outcomes than district-run schools for Black male students, who historically have lagged behind other student groups. “You don’t have those students and their families suffer.”
Henderson was part of a group of Black men who rallied on behalf of Urban Prep. The charter organization sued CPS and was allowed to keep two schools open.
Henderson says CPS needs to better support charter schools. He is sympathetic to the argument that charter school operators should receive a funding boost from CPS.
Henderson said he would commission a forensic audit. If it turns out that CPS needs additional revenue, he said he has the skill set to go to Springfield and make the case.
He said he wants to serve because he cares deeply about education.
“Men who are educated are more likely to get married, have families. You feel better about yourself,” he said. “The data shows that the more education you have, as a general rule, the more you make. Education is just transformational.”
Read Henderson’s full questionnaire.
School board member Jessica Biggs says her experience leading last year’s search for the district’s leader motivated her to run for president.
Biggs says she successfully secured buy-in from all board members on the job description for the superintendent after what she calls an “authentic” process of gathering community feedback.
“So that just showed me what was possible if there was leadership,” she said.
But the process fell apart after the candidates’ names became public and one dropped out. Biggs said she believes what happened was driven by political divisions on the board, leaving her demoralized to such an extent that she decided she didn’t want to run again as a board member.
“There were times when I very much wanted things to move forward, or be brought for a public vote, and was not able to do that,” Biggs said.
To have the impact she was seeking, Biggs realized, she needed to take a lead in setting the board agenda. The way to do that was to run for board president, Biggs said.
“If I was going to continue to spend my time on this board,” Biggs said. “it was important to me to be able to have that authority.”
Biggs grew up in Wheaton, now lives in Douglas, and has one daughter, who attends a fine arts magnet school.
Biggs was one of three members elected in 2024 without the backing of powerful interest groups, including the Chicago Teachers Union and the Illinois Network of Charter Schools. She won her race with about 45% of the vote despite being massively outspent. On election night, she said she felt like people wanted independent board members. “I feel really loved,” she said.
She works for the Southwest Organizing Project, a community organization on the Southwest Side on an initiative that connects school communities with a range of services.
Biggs was fired as principal of a South Side elementary school in 2018 after an inspector general report found that she instructed staff to mark students as tardy even if they missed much of the school day and had them pick children up in their cars without getting written permission from their parents.
She was put on CPS’ “Do Not Hire” list. But she was removed last year, after previous attempts to get off the list were denied. Biggs has contended that her firing was political.
In her two years on the board, she opposed some of the biggest measures pushed by mayor-appointed and CTU-aligned members. She held firm last year against the push to take a loan to avoid cuts. This summer, she voted against an amendment that reversed layoffs by assuming the state would provide more money for CPS.
Since she ran two years ago, she’s gone from a “no” on school closings to leaving the question blank on our CPS School Board questionnaire. She says she doesn’t think there is a yes-or-no answer.
“I think this is a false dichotomy,” Biggs said. “There are spaces in this district where kids’ needs are being met by small schools, and there are spaces in this district where kids’ needs are not being met by what we are offering in a school.”
Read Biggs’ full questionnaire.
Revuluri, the first to declare his candidacy more than a year before the election, says he would lead a board laser-focused on student outcomes. A board appointee during Lightfoot’s administration, he has leaned into criticism of the current board, arguing it has gotten caught up in political squabbling and left pressing issues such as declining enrollment unaddressed. The board is now partly appointed and partly elected.
“Our students need a board that will be entirely focused on their success and willing to confront the current reality,” said Revuluri, the father of two CPS students.
Revuluri was a founding teacher at a public high school in New York City. He also worked in the CPS Department of High School Teaching and Learning and at the University of Illinois Chicago, where he led the Suburban Cook County Mathematics Initiative. A former “Jeopardy!” winner and Local School Council member, he worked at an investment firm and more recently as an education consultant.
He acknowledges that the CPS board on which he served as vice president also became consumed by politics. Revuluri holds himself and his board responsible for not reopening schools for in-person learning sooner during the COVID-19 pandemic, “to the detriment of our students,” though he notes the profound uncertainty the district was navigating.
Revuluri said the school board should drive more dollars toward programs proven to help students. He criticized the ongoing expansion of “Sustainable Community Schools,” which Dominguez and other CTU-backed candidates have vowed to continue expanding. A partnership between the union and district that gives high-needs schools an extra $500,000 a year to team up with community nonprofits, the program has drawn some scrutiny for thin evidence that it has improved student outcomes.
“There’s a big gap between the rhetoric and ensuring actual results that matter,” he said.
He also blasted the board for recently passing a budget that assumes $150 million more from the state that isn’t guaranteed.
Revuluri indicated he would not close schools to balance the district’s budget in our CPS School Board questionnaire in July. He explained in an interview that the district should resort to mergers only to improve the experience of students in schools that have become too small to meet their academic and social needs. Any such plan must start with deep community engagement, he said.
“Chicago is not alone in facing these changes, but we have been exceptional in how much we have pretended and been in denial,” he said. “What pretending has delivered for our students is an impoverished educational experience.”
Read Revuluri’s full questionnaire.
After months of speculation about the candidate the CTU might champion for the board’s top job, the union settled on one of its own when it endorsed Dominguez, who left his job at the union before launching his campaign. Dominguez says he’s unapologetic about his yearslong role as a union stalwart. The only presidential contender who worked as a full-time CPS teacher, he is also the husband of an assistant principal in the district.
Dominguez says his education advocacy goes back to his time as a student at Whitney Young Magnet High School, when he organized a walkout to protest budget cuts in 2010.
A native of the Pilsen neighborhood, he worked as a special education teacher on the Southwest Side. He took two years off to focus on political campaigns, including his own failed City Council bid. He later helped organize an 11-day teacher strike in 2019, when he was arrested with other union members holding a sit-in protest at the offices of the failed Lincoln Yards megaproject. Trespassing charges against him and the others were later dropped.
After going to work for the CTU full-time in 2022, Dominguez also worked on Johnson’s breakout campaign and on the candidacies of CTU-backed school board members in 2024. The union handily outspent well-resourced pro-school-choice groups in those races. It helped secure wins in three of nine contested races.
Dominguez said he has made more than 100 lobbying trips to Springfield over the years, “more than all my opponents put together.” So far, though, the push to secure an influx of additional state revenue for schools has fallen flat. Dominguez says that as president, he would work to engage more families in lobbying and rally districts statewide.
He is proposing offering free, full-day preschool to all city 3-year-olds through a partnership with private childcare centers and home-based daycares. He says the shift would drive economic development, boost the district’s enrollment, and “do right by families” by easing childcare costs.
Dominguez’s other priorities are also closely aligned with the union’s. He said he will push for better cafeteria food and the continued expansion of the Sustainable Community Schools program.
He staunchly opposes any school closures, arguing that the district and city should instead use vacant space in “supposed underutilized schools” to expand services such as healthcare clinics and library branches.
“When we talk about underenrolled schools, we should be clear that we’re talking primarily about Black and brown students in Black and brown neighborhoods that deserve more investment and not punishment,” he said.
In 2021, Dominguez faced a complaint from a fellow teacher who claimed Dominguez made a Nazi salute, called him Hitler in front of students, and questioned that teacher’s sexual orientation. The complaint was later withdrawn. Dominguez called the complaint “baseless” and said he was standing up to a racist colleague who had disrespected a student.
Read Dominguez’s full questionnaire.
Mila Koumpilova is Chalkbeat Chicago’s senior reporter covering Chicago Public Schools. Contact Mila at mkoumpilova@chalkbeat.org.
Sarah Karp covers education for WBEZ. Contact Sarah at skarp@wbez.org.