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.
A retired Chicago Public Schools teacher appointed by the mayor is facing off against a former special education teacher worried about the school district’s debt burden and a data scientist focused on securing more funding from the Illinois legislature.
Incumbent Debby Pope is endorsed by the Chicago Teachers Union, Kyna Lenhof has the endorsement of the anti-CTU Common Ground Collective, and Daniel Basco has positioned himself as “a fiercely independent voice.”
District 2b is one of Chicago’s most culturally diverse areas and is home to 18 public schools. The three candidates running to represent the district all listed adequate classroom funding and resources among their main priorities, but their thoughts on how to secure that funding vary.
Pope said she supports increasing funding for schools by taxing the rich, while Basco said he wants CPS to get more funding from the state. Lenhof, meanwhile, said she wants to reduce the district’s reliance on high-interest loans.
Pope was appointed to the board by Mayor Brandon Johnson in 2024 after the mass resignation of his first group of school board appointees amid tensions with former CPS CEO Pedro Martinez.
She got the nod from the powerful teachers union, while Lenhof was endorsed by The Urban Center, a centrist political organization that supports charters and advocates for school choice across public and private schools. Lenhof was also endorsed by the Common Ground Collective, which is heavily funded by billionaire Michael Sacks and says it aims to engage voters around “effective progressive policies.”
Earlier this summer, Common Ground released an ad attacking Pope for voting in favor of a CPS budget plan that assumes the district will receive $150 million more in state funding than projected.
The day before the vote, Lenhof also released a statement criticizing Pope.
“Our current board member, appointed by Mayor Brandon Johnson, has continually supported high-interest loans that burden taxpayers and weaken CPS’s financial future,” Lenhof wrote.
Both Pope and Lenhof have touted their experience working in classrooms, while Basco has positioned himself as an independent and highlighted his work researching education policy.
Raised in New York, Pope has lived in Chicago for more than 50 years and in Andersonville for nearly 30.
She taught high school for close to 20 of those years, primarily working as a bilingual social studies teacher. After retiring from teaching, Pope worked for the CTU for just over a decade, serving in various roles.
Pope was a strong advocate for bilingual and dual-language education during her first term on the school board, informed by her experiences in the classroom. When she started her career at Benito Juárez Community Academy High School, many of her students were newly arrived immigrants from Mexico. Pope wasn’t fluent in Spanish at the time but said she would read a Spanish dictionary every night after work to develop her skills.
“I saw school as an opportunity to help kids who had come as immigrants to find their footing in the United States,” she said.
Pope’s two daughters also attended CPS schools, graduating from Whitney Young Magnet High School while she was teaching at Gage Park High School. Her granddaughter currently attends Inter-American Magnet School, a dual-language school in Lakeview.
“The contrast in what was available to my daughters versus what was available to my students was painful to see every day,” Pope said. “My one daughter, she took four different art classes, and my other daughter was in concert choir, and they were both on the swim team. Gage Park didn’t have those things and I wanted all kids to have those opportunities.”
Pope said it’s important to ensure funding is equitably distributed. She’d like to see a graduated income tax and the closure of corporate tax loopholes so that the wealthy contribute more to public education.
Pope’s top donor as of mid-September was the political arm of the CTU.
Read Pope’s full questionnaire.
Lenhof moved to Chicago 25 years ago to take improv classes at The Second City. While there, she started working at Easterseals Academy, a therapeutic day school for students with autism, and later worked as a special education teacher at Scammon Elementary School in Kilbourn Park.
“I was inspired to run because I really do believe that every child should have access to a safe, equitable, and joyful education,” said Lenhof, a Bowmanville resident of 13 years.
She now works for KMM Consulting, a political fundraising and strategy firm that helps local candidates and nonprofits organize events and fundraise, and serves as treasurer for the 40th Ward Democrats. She also continues to perform and hosts a variety show in Andersonville.
If elected, Lenhof said she’d like to see CPS get more funding for special education, ensure that individualized education programs, or IEPs, are followed by all educators, and provide adequate support to special education teachers.
“My priorities really boil down to: How do you do the right thing for your most vulnerable populations?” Lenhof said.
She also said she would push for a budget that reduces the district’s borrowing as much as possible and avoids “more high-interest loan rates versus money that can go directly into the classroom.” Any money should be distributed equitably throughout the district, she said.
Lenhof’s two biggest donors among political action committees as of mid-September were the Common Ground Collective PAC and INCS Action PAC, a statewide group focused on promoting publicly funded, independently run charter schools.
Read Lenhof’s full questionnaire.
A Texas native, Basco studied policy analysis at Northwestern University. He worked in data science and got his Ph.D in policy analysis from the RAND School of Public Policy in California before moving to Andersonville five years ago.
Under the Obama administration, Basco advised the U.S. Department of Education on policies related to funding science education and worked with community colleges in Texas to evaluate the effectiveness of their courses.
In his current role at Kindsight, which provides fundraising tools to the education, nonprofit, and healthcare sectors, he builds technology to help nonprofits find donors.
“My approach is always, ‘How do you collect as much data as possible? How do you look at the problem from every angle?’” Basco said.
If elected, Basco said he would advocate for more state funding and push for multiyear CPS budgets to give students and families more consistency.
“What I’ve heard from parents is the uncertainty around the budget means uncertainty about programs, about after-school, about English language programs,” Basco said.
Basco, who works with artificial intelligence for a living, also said CPS needs stronger guardrails around AI. While AI can be a tool to help learning, Basco said the district needs to ensure students’ data and privacy are protected.
“The space is evolving so quickly so we need folks who are up-to-date about what’s going on to help shape policy,” Basco said.
Basco has emphasized his independence; on his website, he says that he is “beholden to no political machine.”
Basco said being an independent candidate means having “empathy for every audience.”
“I’m going to look at issues from every level and I will hear from everybody to try and find potential solutions,” Basco said.
As of mid-September, Basco had donated $7,000 to his own campaign and had reported no additional donations.
Read Basco’s 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.