For months now, two Chicago School Board members, a former one and an attorney have been out raising money and gathering signatures in an attempt to become the first-ever elected president.
But it wasn’t clear until now who the powerful Chicago Teachers Union would support. The answer is Hilario Dominguez, the union’s own deputy political director, who told WBEZ he plans to file his nomination petition by Tuesday.
He joins Jessica Biggs, Jennifer Custer, Victor Henderson and Sendhil Revuluri, who filed their paperwork earlier this week. Candidates have until Tuesday to come forward, so that list could grow.
It’s a high-stakes race because the president has the power to decide what issues get debated and brought up for a vote. The president is the only citywide position that all Chicago voters will get a chance to weigh in on and it’s likely to attract big campaign contributions.
Dominguez’s association with the teachers union will be both a blessing and a curse. The CTU has been on the front lines of pushing for improvements in schools, and many parents and other voters trust the opinion of teachers and school staff.
But right now, the majority of the board and the president are appointed by Mayor Brandon Johnson, and some of Dominguez’s opponents are eager to see Johnson and the CTU lose that control.
The question of whether Dominguez is too close to the union is already being debated. For example, when CTU President Stacy Davis Gates recently accused billionaire political donor Michael Sacks of pushing for school closures, among other things, Sacks called Dominguez a “paid deputy.” Then Sacks said he will support candidates who want a “truly independent student-centered” board so long as Davis Gates backs candidates like Dominguez.
WBEZ and the Chicago Sun-Times spoke with the five candidates about why they are pursuing the president’s seat, what sets them apart from other candidates and where their support will come from.
Jessica Biggs
For the last two years, Biggs has represented a school board district that spans from the Loop to Bronzeville and down into Englewood. She has prided herself as an independent.
She says she decided to run for president because she saw how much of a difference it can make to control the agenda and she thinks the board could be more effective.
“It’s been a rocky start, and for me the decision really laid in wanting this body to live up to the promise that I think it has,” she says.
Biggs works as a community organizer and director of Healthy Southwest, a health equity initiative on the city’s Southwest Side. She stresses that she’s the only candidate who’s been principal of a neighborhood school in CPS.
But she also ran into some trouble as a principal. She was fired from her position at Burke Elementary after the inspector general, the district’s internal watchdog, found she violated CPS policy when she marked students as late instead of absent half a day, and told some staff to pick up students from home and take them to school.
Many in the community thought the investigation and subsequent firing was retribution for Biggs complaining about her school being dirty, after the district privatized the management of its custodial services.
She was put on the district’s “do not hire” list, which prohibited her from working in CPS. After Biggs tried and failed to get off the list, newly hired CEO/Superintendent Macquline King allowed her to be removed. That doesn’t happen often: Over the last decade, 500 of the 4,500 people put on the list have gotten off, according to CPS.
When Biggs ran for her seat in 2024, she was proud to have a grassroots campaign that didn’t tie her to any one political interest.
But as this election cycle heats up, she is taking in more from big donors with specific interests. That includes Sacks and Paul Finnegan, the chair of a private-equity investment firm, and Finnegan’s wife, who have already contributed more than $20,000 to Biggs.
Biggs says she wants to build a diverse coalition like the one that supported her two years ago. Sacks contributed to her first campaign and that didn’t compromise her, she says.
“I think this is a moment, both locally and nationally, that we need to bring people together to be able to hear each other and not sort of be sitting in our separate corners lobbing bombs back and forth,” she says. “I feel really hopeful that I could be a candidate that could do that.”
If elected president, Biggs says she would want board committees to meet regularly and work through issues, something she says the current board doesn’t do.
She also says the board needs to set specific expectations for the district and regularly measure progress.
“How many of our second graders are reading at grade level and are we moving second graders to third grade ready to read to learn?” she says. “That’s not a conversation that I have seen this board have frequently, and that’s something that the school system is ultimately responsible for doing.”
Jennifer Custer
As a sitting board member, Custer represents a chunk of the Northwest Side, including parts of Belmont Cragin, Portage Park and Irving Park. She has three young children and is a former assistant principal and suburban teachers union president.
Custer has emerged as a dissenting voice on the board. She was vocal about her opposition to CPS’ agreement with the CTU to make May 1 a civic day of action, saying her community expressed concerns about finding childcare on short notice, and she was against modifying the approved calendar.
She was also the lone member to vote against hiring King as the permanent superintendent and CEO of the district, citing concerns from school staff in her district and “pressure” to reconsider King after she didn’t make the initial list of finalists.
But Custer has said if she becomes board president she would not automatically seek to replace King. And Custer says they’ve had productive conversations since that vote.
“I think my relationship with Dr. King is just fine and I think professionally it’s my job to support her and help her,” Custer says. “That’s what I intend to do.”
Custer says she decided to run for board president because she’s often asked herself: “What if we did this differently? What if we changed up this procedure?” She thinks the board could be more creative in coming up with new policies that could help students.
“In two years we have not discussed policy in any capacity, other than evaluation of policies that we need to look at,” Custer says. “Even then, there’s not a lot of questions about them, not a lot of digging into what they mean.”
Custer says she’s building a wide coalition of supporters like she did in 2024. That includes labor unions, such as the International Union of Operating Engineers Local 399 and the Chicagoland Operators Joint Labor-Management political action committee, which together have contributed more than $15,000 to her campaign. Other donors include the PAC for the Illinois Network of Charter Schools, Sacks and Finnegan.
If she wins the president’s seat, Custer says she’d dive into how to improve students’ academic performance. She’d like to look at programs across the district and determine what’s working and what’s not.
The district’s financial health is her other pressing issue. While she believes the board president should advocate for more money in Springfield, she says the leader also needs to show they’re willing to “fix our own house” first.
That means having difficult conversations and making “tough decisions,” she says, including what to do as the moratorium on school closings is set to expire in June 2027. That kind of preparation would help the district approach the issue in the right way for communities, she says.
“I’m having a hard time seeing how this will not inevitably be a topic of conversation for the future board,” Custer says. “Certainly it was not done well in the past, but we can’t hide from something just because we don’t like it or are afraid of it.”
Hilario Dominguez
Dominguez is the only candidate who has a CPS answer to the perennial Chicago question: “Where did you go to high school?” He graduated from Whitney Young, where in 2010 he led student protests against school-level cuts proposed by the then-CEO.
With deep family ties to Pilsen, Dominguez ran for 25th Ward alderperson in 2019, but lost to Byron Sigcho-Lopez. His wife is an assistant principal at Whitney Young and they have a 1-year-old son they plan to send to CPS.
Dominguez worked as a CPS special education teacher for six years. There’s been some controversy around his conduct as a teacher. A colleague complained to CPS that Dominguez referred to them as Hitler multiple times, according to his personnel files, which were obtained by the FOIA Bakery, an organization that requests and publishes information about Chicago agencies.
The complaint was eventually withdrawn. Dominguez’s campaign says he was standing up for students facing discrimination from that colleague and that “he called a racist, racist.”
In 2022, Dominguez took a job as political organizer for the CTU. He is taking a leave from the union to run his campaign. He’s yet to open a campaign committee to take in contributions.
Dominguez won’t have the CTU’s endorsement until he and others go through the union’s official process, which includes an interview and other vetting. But he, of course, is well-versed in their positions and believes in them. Still, he pushes back on the assertion that his ties to the CTU are problematic.
“The real question for voters is: Who do we trust to shape public education?” he says. “Teachers and parents who have dedicated their lives to our children, or billionaires and privatization interests that have spent decades destroying them?”
Dominguez notes that he has been on the “front lines” pushing for smaller class sizes, and more librarians, school nurses and social workers. If he became board president, he says he would see himself as the Avenger leading a team trying to get more money for schools and prevent school closings.
Dominguez also rejects the idea that CPS needs to make “hard choices” to balance the budget. He says CPS could save some money by scrutinizing contracts and other spending, but for the most part he insists that more state funding is the answer to the district’s budget problems. He’s made dozens of trips to Springfield lobbying for just that.
He, like the CTU and the mayor, point to the fact that CPS would get nearly $2 billion more if the state budgeted enough to meet its school funding commitments. CPS estimates its current deficit is $732 million.
“CPS is not struggling because students are receiving too much,” he says. “It’s struggling because the state hasn’t met its obligation. … If you don’t pay your light bill, it gets cut off. That’s the same type of pressure that our state needs to feel in order to provide for our students.”
Victor Henderson
Victor Henderson’s name is well-known in Chicago’s legal world but it’s not as recognizable among educators, though he’s spent nearly three years on the board of the Urban Prep Academies charter network.
Meeting minutes for the once-lauded, but recently troubled, operator noted that Henderson “publicly and avidly supported Urban Prep” through its issues.
Henderson was among a group of African American leaders that spoke out in 2023 against plans for CPS to take over operations of Urban Prep after the school board voted to revoke the network’s charter. That vote came as Urban Prep’s founder and former CEO, Tim King, faced allegations of sexual misconduct and CPS’ inspector general put out a damning report that detailed mismanagement and misspending by the operator.
Since then, federal prosecutors have charged Tim King with stealing more than $100,000 from the charter network.
Henderson did not respond to a request sent to his spokesperson to discuss his involvement in Urban Prep.
Henderson says he’s running for board president because “there’s an opportunity to help children” and he knows a good education can be “transformative.” Henderson says he’s a product of public schools and that he sent his children to CPS.
Henderson started his career as a public accountant before he pivoted to law school. He worked in commercial litigation and later founded his own firm, Henderson Parks, which specializes in business-related disputes and also handles cases involving bank fraud, embezzlement and other white-collar crimes.
He’s represented well-known figures in high-profile cases, such as state Sen. Emil Jones when he was accused of bribery and lying to the FBI.
Henderson has contributed $30,000 to his own campaign so far. Most of his other contributions have come from individuals.
Henderson says his experience handling complex legal cases will help him navigate a district as layered as CPS. And he says his background in accounting will give him an advantage in tackling the district’s deficit and debt. He also wants the district to be more clear with families about how it’s spending its money and show that it’s reaching students.
“Your neighbors and mine need to know that the system is working to advance the educational interest of the children,” Henderson says.
He’s also focused on improving math and reading performance and increasing graduation rates. Henderson thinks the school board spends too much time on matters outside the classroom. The board should treat children like their “clients,” he says.
“We need to have more focus on what’s going on in study hall and far less focus on what’s going on in City Hall,” Henderson says.
Sendhil Revuluri
Early in his career, Revuluri worked as a math teacher at a Bronx public school. He also spent time in CPS’ Office of High School Teaching and Learning and at the University of Illinois Chicago’s Metro Chicago Math Initiative, which is focused on improving math education.
Revuluri was appointed by Mayor Lori Lightfoot to the school board in 2019. Though Lightfoot still held the reins of the board then, members spoke out more and not all votes were unanimous. In one of the most controversial decisions of his tenure, Revuluri voted with the majority of the board to keep police officers in schools. Eventually, when Revuluri was no longer a member, the board eliminated those officers.
Revuluri resigned from the board in 2022 to take his family on a yearlong excursion around the globe. He says he wanted to show his two children how other people in the world lived and teach them empathy.
Revuluri says his school board experience made him want to become president. He says the role and board goals were not clearly defined when he served. That, he says, became problematic when the board was grappling with CPS’ move to remote learning during the COVID-19 pandemic followed by the return to in-person learning.
After that, Revuluri became certified as a governance coach and started working with other school boards.
“Seeing these other boards that had the commitment to put students at the center and the courage to make changes, even if they were unfamiliar or uncomfortable, made me feel much more optimistic that boards can influence the conditions for learning in a positive way,” he says.
He says so far, he has not seen Chicago’s board get organized in this way, but he believes he can make that happen.
Revuluri starts out with the most money in his campaign coffers. He’s raised more than $275,000. A lot of his donations are from individuals who live in Chicago, but about 60% are from people in the suburbs or out of state, according to the contributions filed with state election officials.
He’s also getting some early support from Chicago Democrats for Education, which is chaired by heavyweight political consultant Hugo Jacobo.
Revuluri has sharply criticized the performance of the current school board. Earlier this month, he called out some members for saying that “Springfield owes us a billion dollars.” While he acknowledges that CPS doesn’t receive adequate state funding, he called it a performative “slogan” that doesn’t change anything.
It “isn’t a budget, doesn’t pay staff, doesn’t teach a single kid to read,” he says.
Revuluri says the board needs to make “hard calls” to balance the budget, though he didn’t spell out what those might be, and focus on spending that improves learning.