Most of the state has one, and indeed most of the country, but with the often bare knuckled politics of the Windy City, this was not a given, and both critics and observers are feeling this is one for the record books, but that supports or belies the often rough and tumble politics of Chicago, plus who says what, and when, but is not always obvious.
For example, while the Chicago Teachers Union, one of the most powerful unions in the country, they have their own preferred candidates for both the board and the presidency, but there is substantial opposition by some groups, especially those who favor charter schools, and then again there are those that oppose the CTU on principle, many of whom are on the other side of the liberal tenor of the city, and, as some predicted, have the support of the Republican party and the Trump administration.
With 20 members and a board president to be elected there is money behind some candidates, real money, $2 billion for Debby Pope on the city’s Far Northside that includes the Lakefront area of Edgewater which encompasses a mixture of Gen Xers, affluent singles, families, and recent college grads; as well as old school baby boomers, and retirees creating a laboratory, of sorts, for what might be one of prediction, as well as predilection.
Recent reports are pitting Pope, a grandmother and retired school board teacher, with Kyna Lenhof, a special education teacher and one that wants to confront the rising costs of public education in Chicago, as it faces a deficit of $732 million.
Both Pope and Lenhof do have dedicated classroom experience, but with some variance on funding. Opposition to the former comes from the Illinois Charter Schools Association and while campaign flyers from them say they are not authorized by Lenhof, or that she is responsible for their statements some critics say the support is for more charters, that many residents say they don’t want stating the dichotomy of a private school system paid for with public monies embedded in a public school system.
Pope on the other hand has the backing of CTU, which in the eyes of some anti-union residents automatically gives her a failing grade.
Lenhof does gain support from Common Ground Collective, who has been broadly identified as “an independent, 501(c)(4) dark-money issue advocacy organization in Chicago. The group has been actively distributing political flyers and electioneering at Chicago Public Schools (CPS) events, sparking local controversy and ethics concerns regarding school privatization efforts,” and supported by wealthy donor and Chicago businessman Michael Sacks.
Collectively, outside of the CTU both CGC and INCS, according to public reports, have spent $4.6 million against the union backed candidates.
While these are but two of the board candidates they represent a reckoning of shorts between money philanthropy, politics and the teachers union leaving many wondering which direction CPS can continue to not merely function, but grow, amidst the economic and racial dynamics of a city that has faced both, along with declining enrollment of 20 percent, according to most recent data.
Keeping that in mind confronting this cost was a factor in the dismissal of former school CEO Pedro Martinez who rejected a $200 million dollar loan proposed by Mayor Brandon Johnson and supported by Pope; a move that critics say would have harnessed Chicago residents with higher takes for years to come but supporters say with the absence of money from the State government, where would the financing come from?
Chicago is the nation’s fourth largest city school system with a student population of 320,000 to 324,000 students, many of whom are Black and Brown and facing great economic challenges, and needs, not all of which cannot be handled in the classroom and face equally high numbers of truancy and disruptive student behavior, and has previously either not been adequately dealt with, or dealt with punitive behavior that critics say has been an overreach, including, but not exclusive, of physical restraint.
The seesaw effect of collective reading and math scores has led some conservatives to propose closing schools, as was done in 2013 by former Mayor Rahm Emanuel and that led to widespread criticism as they occurred in mostly low income communities of color and that were community anchors; and, now these vacancies have become places for violence and crime. Coupled with low enrollment school closings could be a consideration.
In a recent WBEZ report, English and Language Arts have increased to 45.7, up from a ranking of 42.81 percent in 2025; and Math scores are 290 percent up from 27.3 in 2025; but for all of the goods news it shows that Chicago public schools are below average state scores showing 56.4 percent in ELA and 39.6 in math with grades 3-8 as seen on the Illinois Assessment of Readiness.
“In Chicago, the percentage of students considered proficient in ELA increased by 3 percentage points to nearly 46% — a jump that paralleled the state’s gains. CPS Director of Literacy Jane Fleming attributes that performance to the district’s “standards aligned and culturally responsive” initiatives. The increased proficiency is especially impressive considering the district’s large English learner population, which also saw small gains, Fleming said.”
Teachers have told us that there are many factors outside of the classroom that affect both performance and test scores, as well as absenteeism, and disruptive classroom behavior, often stemming from parental control and emotional upheavals
Add to those factors English learners whose first language was other than English and the challenges increased with the influx of Venezuelan immigrants after the bussing from Texas Gov. Greg Abbott began in August 2022 swelling the school system and facing a critical shortage of bilingual teachers.
One more caveat: the presidency of the school board has been another financial blockbuster. $8.7 million has earned eye-watering reactions with current board member Jessica Biggs, CTU political director Hilario Dominguez, and attorney Victor Hernandez. Once again following the money Biggs $1.85 million over the last several months, and support from SEIU, plus a cool $1 million from Sacks
Dominguez got $1.75 million from CTU and affiliate Our Schools PAC. Henderson comes in last with self-funded $737,000.
All of the money withstanding, and it is significant, but the proof of the pudding is in its eating, and a greater awareness of the election has given Chicagoans bodes well for a more targeted approach to the myriad of issues facing CPS -- but with a city of strong shoulders tackling a legacy of distrust, racial and economic segregation, it may be all over but for the fighting.
