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.
An attorney and a businessman are challenging an incumbent with a background in community organizing in a three-way race to represent one of Chicago’s most culturally diverse areas along the Far North Side lakefront.
Elected in 2024, Ebony DeBerry favors taxing corporations and the wealthy to confront Chicago Public Schools’ budget woes. Her opponents both see belt-tightening as a path forward. Bruce Leon, an entrepreneur and 50th Ward Democratic Committeeperson, is looking to cut wasteful spending, and Hector Morales, an attorney for the Illinois Department of Children and Family Services who attended CPS, said the district must spend more efficiently.
District 2a is home to a large number of immigrant families. More than 80 languages are spoken throughout the Rogers Park neighborhood alone, according to the Rogers Park Business Alliance.
The three candidates’ views differ on how to fund and invest in bilingual and dual-language education programs while also addressing CPS’ budget deficit.
“We have to find ways to make corporations, millionaires, and billionaires pay their fair share,” DeBerry said during an interview, while Morales said board members “need to make sure we’re using what we got now, before we start asking folks for more money.”
DeBerry, a former CPS teacher, won 43% of the vote in 2024, edging out three other candidates, including Leon.
DeBerry has been endorsed by the Chicago Teachers Union, while Morales has been endorsed by the Common Ground Collective, an anti-CTU political action committee that is heavily funded by billionaire Michael Sacks and says it aims to engage voters around “effective progressive policies.”
Last winter the group ran ads attacking Mayor Brandon Johnson’s proposed corporate head tax. The CTU, on the other hand, strongly supported the corporate head tax.
Morales is also endorsed by The Urban Center, a centrist political organization that advocates for school choice across public and private schools.
DeBerry is a lifelong Rogers Park resident and a former CPS student, teacher, and parent. She graduated from Sullivan High School and taught pre-K, kindergarten, and first grade for CPS in the early 2000s. She also taught in suburban Evanston and Arlington Heights. Her son graduated from Northside College Prep, a CPS selective enrollment high school, in 2021.
DeBerry said her work as a teacher and with ONE Northside, a nonprofit that helps get neighbors involved in various community issues, has shown her the importance of engaging with students and their families.
“Our life experience makes us experts on what we need,” DeBerry said. “I think that that’s why I value community schools so much — an initiative that brings programming and resources to schools based on the needs of that school community. They don’t all look the same because every school needs something different.”
If elected to a second term, DeBerry said she would like to establish a youth advisory council so the board can hear directly from students.
“We need to hear from a wide swath of opinions, of personal expertise, of community expertise,” she said.
The state needs to tighten its policies around charter schools, DeBerry said, so students aren’t left stranded when schools abruptly close, as happened with the Acero charter schools in spring 2025.
“We had seniors who didn’t know if they would be able to graduate together, who didn’t know if they would be able to have a prom,” DeBerry said. “It was heartbreaking.”
DeBerry would like CPS to start creating multiyear budgets that account for rising wages and building maintenance costs so there are fewer last-minute cuts at the beginning of the year. She also said the city’s taxing system needs to change, and that the wealthy need to contribute more to CPS.
“We are crippling our homeowners, who are not all wealthy,” DeBerry said. “We have a very unfair taxing system — the working class, the middle class, take care of everything in this city.”
DeBerry’s top group donor as of mid-September was ONE People’s Campaign.
Read DeBerry’s full questionnaire.
Leon is a fifth-generation Chicagoan who lives in West Rogers Park. He is a 50th Ward Democratic committeeperson and an influential member of Chicago’s North Side Orthodox Jewish community. He graduated from Highland Park High School, and his four daughters attended Arie Crown Hebrew Day School in suburban Skokie.
Leon ran for the school board in 2024 but lost to DeBerry with 20% of the vote. He also launched a campaign for Illinois’ 9th Congressional District seat last year but said he chose to drop out due to pressures from AIPAC, a pro-Israel lobbying organization. The writer of an independent voter guide posted that Leon is circulating petitions to run for city treasurer in February. Leon did not respond to questions on that potential run.
In 1998, Leon started Tandem HR, an outsourcing human resources firm, with just three employees. He grew the company to more than 200 employees and sold it in 2024.
Leon said he believes his experience running a business would serve him well on the school board.
“Out of the 21 board members, wouldn’t it make sense to have a business owner who loves Chicago, who wants to make this huge organization of 42,000 employees run efficiently and effectively?” Leon said.
He said it’s important to have a variety of expertise represented on the board.
“To think that everyone should be a kindergarten teacher, or be a union member, in order to be on the board, is preposterous,” he said.
Leon said CPS should address the budget deficit by cutting back on excess staff and converting schools with low attendance into charter schools or vocational schools.
Leon did not have any campaign donations as of mid-September, according to State Board of Elections records.
Leon did not respond to our questionnaire.
By day, Morales is an attorney whose private practice specializes in business licensing, real estate, and zoning. But Morales also has a passion for electronic music, and recently got a degree in sound arts and industries from Northwestern University.
Morales, who attended Senn and Roberto Clemente high schools before graduating from Truman Middle College Alternative High School, said music didn’t feel accessible to him until his 30s, when he took a class in circuit bending.
Morales took his niece’s broken keyboard, hooked it up to his laptop, and started making his own electronic music.
“It showed me that anything can be musical,” he said.
Morales said he was inspired to run for school board after volunteering at Gale Elementary School in Rogers Park, where he taught kids how to make electronic music.
“I noticed kids that were shy at first would get up there and start making music and their faces would light up,” Morales recalled.
If elected, Morales said he would like to make music and the arts part of schools’ core curriculum. Nurturing students’ creativity makes them better, more well-rounded students, he said.
A Loyola University alum, Morales grew up in the Lathrop Homes public housing project and was the first person in his family to graduate from college. College felt like a possibility for him largely because a Loyola student tutored him while he was in high school, he said. Morales said he would like to see CPS partner more with local universities to show high school students that college is an option.
Morales said running his own law firm since the early 2000s has given him experience balancing a budget. If elected, he said he wants to make sure CPS is “using every dollar as efficiently as possible.”
Morales did not have any campaign donors as of mid-September, according to State Board of Elections records.
Read Morales’ full questionnaire.
Molly DeVore covers Chicago’s Far Northwest Side neighborhoods, including Portage Park, Jefferson Park, Norwood Park, Forest Glen, and Sauganash, for Block Club Chicago. Contact Molly at molly@blockclubchi.org.