By Steven Jiang, Editor-in-Chief

In a bitter three-way race for president of the Chicago Board of Education, Victor Henderson embraces his outsider status.

The 65-year-old trial attorney, a Wharton and Georgetown Law School alum, has represented numerous high-profile clients including Jussie Smollett and the City Colleges of Chicago. Henderson has served as an ethics counsel to the Chicago Housing Authority and the U.S. House Ethics Committee. He is also a certified public accountant. But beyond his tenure on the board of Urban Prep Academies, his resume lacks education-related work.

That doesn’t bother Henderson. “I’ve been a consumer of education,” he insisted in an interview with The Paw Print, shrugging off claims of inexperience. “Just because I haven’t been a teacher or a principal doesn’t mean that I don’t have experience in education.” He added that his four children all attended Chicago Public Schools.

In the city’s upcoming school board election, voters will choose all 21 members for the first time — ending over a century of mayoral appointments. The presidential race pits Henderson against former CPS principal Jessica Biggs and Hilario Dominguez, a former teacher and union leader. A proxy battle has emerged between the powerful Chicago Teachers Union (CTU), which backs Dominguez, and the Service Employees International Union (SEIU), which endorsed Biggs.

“Sometimes people in the system are in the system for so long,” Henderson remarked. “Of course, people will tell you that they’re not going to compromise their views and interests. They have to say that. But I don’t have those constituencies to contend with, to answer to [and] to pay back.”

He reiterated his independence from special interest groups and wealthy donors, who have already poured $6 million into the elections. Earlier this month, anti-CTU billionaire Michael Sacks donated $150,000 to Biggs. By contrast, Henderson has personally funded most of his campaign’s cash, which totals over $600,000. He has earned endorsements from several prominent Black politicians and pastors, including Rep. Danny K. Davis and Bishop Byron Brazier.

As tensions run high between the candidates, accusations have flown. Dominguez has faced allegations of sexually harassing a colleague in 2017, which the district’s inspector general did not sustain. Biggs was fired and temporarily blacklisted by CPS for allegedly tampering with student attendance records as principal, although she claims it was politically motivated. Henderson has denied child abuse reports from a previous marriage, defending his use of corporal punishment in certain circumstances.

The fierce partisanship within the race reflects the dysfunction that has permeated Chicago’s education system over the past few years. In 2024, Mayor Johnson’s demand for a $300 million high-interest loan — backed by the CTU — caused a standoff between City Hall and then-CPS CEO Pedro Martinez, culminating in the resignation of the entire school board and the eventual firing of Martinez. On a narrow 11-7 vote this July, the board approved a controversial budget that assumed $150 million in state funding that has yet to be secured. Clad in their signature red shirts, CTU members lobbied intensely for the measure, while the SEIU expressed concerns of fiscal irresponsibility.

The current instability takes place against the backdrop of declining enrollment and lagging proficiency rates across CPS. According to Henderson, now is the time for an independent leader with a proven track record in board governance.

Henderson characterized his leadership style as mission-oriented and vowed to catalyze a “culture change” within CPS, citing Chicago Bears coach Ben Johnson as inspiration. He once again blamed “people with their own agendas” for injecting politics into the school system. Regarding his relationship with City Hall, he promised transparency with the mayor and called him a “partner.”

Touting his experience as president of the Chicago Bar Association, Henderson emphasized an interdisciplinary approach. “You need to have some teachers on the board. You need to have some community activists on the board. You need to have some principals on the board, but you also need lawyers and accountants because, you know, those issues loom large in the system,” he said.

But what about the influence of the unions who bankroll his opponents? Henderson affirmed that “everybody deserves a seat at the table, whether it’s CTU, SEIU, billionaires, millionaires [or] people who are of modest income.” He refrained from criticizing anyone in particular despite his claims of systemic incompetence within the district.

Citing his accounting credentials, Henderson slammed the additional $150 million as irresponsible “speculative” budgeting. But he remained vague as to how exactly he would solve the district’s financial woes and deliver on his commitment to not raise the property tax rate unless absolutely necessary.

Nor did he explain how he would fund resources to close the educational outcome disparities within the district. Henderson’s plan is simple: increase time in the classroom and access to tutoring. The rest, he argued, is a mentality issue — one that requires accountability, incentives and passion for learning. He lauded Walter Payton College Prep as a model for all CPS schools to follow.

“There’s an environment of ‘we’re going to do well’ at Payton,” said Henderson. “And that environment… needs to exist at every school.”

How that framework will be implemented across CPS — which encompasses neighborhood, charter and selective enrollment schools — remains an open question.

Henderson’s involvement in Chicago’s charter schools may offer some clues. In 2023, he joined the board of Urban Prep Academies, which operates two campuses in Englewood and Bronzeville. The network has been recently marred by controversy, mostly surrounding founder Tim King’s indictment for embezzling over $100,000 on top of sexual misconduct investigations. Henderson defended Urban Prep Academies against a CPS takeover of the charter system, citing high college matriculation rates for the predominantly low-income Black male student body. He criticized the district for treating charter schools like “stepchildren,” alleging unfair treatment and funding practices.

When asked directly about his support for charter schools, though, Henderson clarified that he is merely “a fan of excellent education…no matter who provides it.”

He is also open to consolidating neighborhood schools that operate below 70% capacity, which constitute over half of the district, under three conditions: similar educational quality across schools, safe student commutes and community involvement in decision making.

“They have to be involved because in 2013, they weren’t involved,” Henderson said, referring to the closure of 50 struggling schools over a decade ago, the largest mass shuttering of schools in American history. He further warned against “billionaires and special interests who don’t…live in those communities making decisions.”

Henderson also expressed support for reinstating school resource officers (SROs), which the school board unanimously voted to remove at the start of the 2024-25 school year due to concerns about racial profiling against Black students and exacerbation of the school-to-prison pipeline. Still, according to the CPS Youth Risk Behavior Survey, 40% of students reported witnessing violence at school in 2023. The decision to employ full-time police officers, Henderson argued, should be left up to each individual school. He added that their presence could foster a “great environment whereby the students get to know the police and vice versa…[in] a city where police and students are adverse to one another.”

For his closing message to voters, Henderson recounted his own educational journey from public schools to his professional career, which unlocked financial freedom. “My life and the life of my children have been transformed by education,” he reflected. “It’s not just about school, it’s really about a way of life…we shouldn’t take for granted. And I think we make society better when everybody has access to a great education. It’s better for all of us. Crime goes down. Happiness goes up. Productivity goes up.”

Henderson’s optimism will face the ultimate test at the polls on Tuesday, Nov. 4, when voters will choose the next leader overseeing the nation’s fourth-largest school district. No clear frontrunner has emerged among the three candidates, and early voting is already underway. Payton students who are 18 years or older on Election Day can register to vote online.