Three parents with children who have passed through Chicago Public Schools are vying for the District 10B seat on the city's Board of Education, a Far South Side contest that pits an incumbent backed by the teachers union against a City Hall critic's aide and a former teacher once barred from CPS hiring. Incumbent Connie Anderson, challenger Patrick C. Watson and write-in candidate Rosita Chatonda each bring sharply different priorities to a district covering some of Chicago's southernmost neighborhoods.
Anderson, a paralegal and mother of twins enrolled in CPS, was appointed by Mayor Brandon Johnson to fill the vacant District 10B seat, according to WBEZ Chicago. Accounts differ on exactly when that happened: Chalkbeat reports she filed paperwork to run in May and was appointed in July, while the Chicago Sun-Times says she filed in June and was appointed in July, and the Chicago Tribune has reported the appointment came in August 2026. Watson, who works as the lead legislative aide to 9th Ward Ald. Anthony Beale, a frequent critic of Johnson, has pointed to the timing of Anderson's appointment as, in his words, indicative of games being played.
Chatonda, running as a write-in, is a former teacher who spent years challenging her CPS firing, a fight that landed her on the district's do-not-hire list, per Chalkbeat's reporting. She says she wants to stand up for Black teachers and make the hiring and firing process more fair, the outlet reports.
Diverging Priorities on Budget and Special Ed
Anderson told Chalkbeat her first priority if elected would be making sure special education is fully funded and that students with disabilities get the support they need to thrive. Watson, by contrast, said his first order of business would be balancing the district's budget, and he told the outlet he's not dead set against school closures if they would help shore up the deficit — a notably different posture from the moratorium debate the Chicago DSA's candidate guide says CPS contenders are being pressed on amid recent enrollment declines.
That enrollment backdrop is real: CPS is now serving nearly 305,000 students districtwide and lost more than 11,000 students in an early headcount for the 2026-27 school year, according to The TRiiBE. Watson has summed up his broader philosophy by saying politics does not belong in education and education belongs in education, per Chalkbeat.
Endorsements Split Along Familiar Lines
The candidates' backers track Chicago's broader education-politics divide. Anderson has the Chicago Teachers Union's endorsement, along with support from the Chicago Principals & Administrators Association and Our Schools Chicago, according to a roundup from WBEZ's education team — the union is broadly aligned with Mayor Johnson. Her campaign has also drawn major donations from CTU's political action committee and the union-affiliated Our Schools PAC.
Watson, meanwhile, is backed by Common Ground Collective and The Urban Center, the same WBEZ roundup shows. Common Ground Collective is an anti-CTU political action committee heavily funded by billionaire Michael Sacks. Watson's major campaign donors also include the Illinois Network of Charter Schools PAC and The Urban Center, both of which support school choice and charter schools. Chatonda, listed in that same roundup under the spelling Rosita Chotonda, had no endorsements on file as of October 2 and has no donations on record.
A Tech Park Divides Candidates on Its Promise
One flashpoint in the race is the Illinois Quantum & Microelectronics Park, a large research and technology facility being built within District 10B. Anderson doubts it will have a positive impact on schools and has cited pushback over a contractual agreement tied to the project, according to Chalkbeat. Chatonda sees possibilities in the development, while Watson has called it an excellent opportunity for CPS, the outlet reports.
A Sprawling District With High Stakes
District 10B stretches across South Deering, Hegewisch, Riverdale, East Side, Chatham, South Chicago, Pullman, Calumet Heights, Avalon Park, Burnside and South Shore, with 21,844 students enrolled, per WBEZ. The district ranks second among Chicago's school-board electoral districts for its number of public schools and students, and Chalkbeat reports that two-thirds of its students are Black and 31% are Latino; the Chicago Tribune separately notes the district's overall population is roughly 67% Black and 26% Hispanic, a distinct population-level figure.
School counts vary by source and definition. The Sun-Times guide lists 56 CPS schools in the district — 43 elementary schools and 13 high schools — while the Tribune describes those same 43 elementary schools as more than any other district has, plus six charter high schools and eight district-run neighborhood and city-wide high schools. Just 7% of District 10B schools are rated exemplary and 29% received a comprehensive rating, according to 2026 data cited by WBEZ.
The race unfolds as part of a historic shift in how Chicago governs its schools: 2026 marks the first election in which Chicagoans choose the entire Board of Education, 20 district members plus an at-large president, the Sun-Times notes in its voter guide. For Far South Side families, the District 10B contest offers three distinct visions for what comes next — from shoring up special education funding to balancing a strained budget to fighting for teachers who've run afoul of the district itself.
