For many years, Chicago served as the focal point for the Democratic Party’s significant shift regarding education policy.

With the backing of long-time resident Barack Obama, then President, and his close ally Rahm Emanuel, who was the mayor, the city moved away from teacher union-favored policies. Instead, it embraced initiatives aimed at providing families with educational choices and accountability, such as charter schools and grading systems based on student performance.

That was the past.

Currently, Chicago is undergoing a radically different experiment: exploring the implications of having one of the nation’s most assertive teachers’ unions elevate a mayor who largely supports its agenda.

On one side, the outcomes have been promising. The district’s 300,000 students are showing remarkable recovery from learning losses caused by the pandemic, and enrollment in college-level courses is at an all-time high.

Conversely, the situation has been marked by financial and political instability. The school district utilized federal Covid-19 relief funds to hire thousands of educators, instructional coaches, counselors, nurses, and social workers, despite a decline in student enrollment.

Now, those funds are dwindling, leaving the district with a deficit of hundreds of millions of dollars. Mayor Brandon Johnson, a former social studies teacher and union organizer, is attempting to remove the schools CEO, Pedro Martinez, who opposed the mayor’s suggestion of taking a high-interest loan to address the shortfall.

In the midst of this conflict, the entire school board resigned recently, replaced by a new set of appointees chosen by the mayor.

The political landscape could change again in the near future. On Election Day, voters will have their first opportunity to elect ten school board members, following years of lobbying by the Chicago Teachers Union to end mayoral control over the school system.

“The Chicago Teachers Union has effectively become the political powerhouse in Chicago,” remarked Paul Vallas, a former schools superintendent and a longstanding critic of the union, who lost to Mr. Johnson in last year’s mayoral race.

Critics of the mayor argue that he should be prepared to reject union demands: to close schools with low enrollment, cut staff numbers, and deny the union’s request for a 9 percent salary increase.

However, Mr. Johnson believes there is little reason to say no, as he feels aligned with the union’s goals. He contends that students in Chicago’s low-income neighborhoods have historically lacked access to quality school libraries, arts programs, language courses, athletics, advanced academics, and valuable career training.

He argues that past antagonistic relationships between mayors and union officials resulted in poor outcomes for Black and Hispanic students, along with a decline in Black teaching jobs.

“What will we commit to and say yes to?” Mr. Johnson posed in an interview. “I was elected to invest in people. Guess what? I am doing just that.”

As a former educator with a strong pro-union stance on educational policy, Mr. Johnson is part of a growing faction of Democrats, including the party’s vice-presidential candidate, Minnesota Gov. Tim Walz.

Their visibility is particularly noteworthy given that the unions’ support for prolonged pandemic school closures led to significant divisions in progressive regions.

However, the political weight of that issue diminished as schools reopened. For major cities like Chicago, New York, and Los Angeles, a pressing concern is sustaining services as student numbers decline, given that funding is allocated on a per-pupil basis.

Over the past decade, families have left urban school systems for various reasons, including high housing costs, dissatisfaction with virtual learning during the pandemic, and the appeal of charter and private schools.

Enrollment figures have increased in Chicago and other cities over the last two years, yet they remain significantly lower than pre-pandemic levels.

In Mr. Johnson’s view, along with that of his ally, Chicago Teachers Union president Stacy Davis Gates, a former social studies teacher, a decrease in student numbers should not translate to fewer schools.

They reference research indicating that when Mr. Emanuel closed 50 schools in 2013, the financial benefits were minimal, and students from those closed schools experienced academic challenges in subsequent years.

Mr. Johnson and Ms. Davis Gates propose instead to invest more in schools that currently have low enrollment. One such example is Frederick Douglass Academy High School on the West Side, which had over 500 students in 2007 but now only has 34.

Both leaders speak in broad, historical terms, framing their agenda as a form of “reconstruction” for Black and Latino students.

“The original goal of Chicago Public Schools was to do two things: maintain segregation and provide the working class with access to the stockyards and factories,” Ms. Davis Gates explained.

In her view, a fundamental reimagining of the system’s purpose is needed for 2024, which she defines as ensuring that every Chicago student has access to a high-quality school within walking distance, complete with bilingual programs, extracurricular activities, and the arts.

She believes the mayor is rightly “impatient and intolerant of further delays.”

The two share a close personal friendship, and both have expressed that their commitment to safeguarding neighborhood schools is informed by their experiences as Black parents raising children in historically Black neighborhoods with struggling institutions.

Mr. Johnson’s oldest son travels to a magnet school in a different area, drawn by its orchestra and Advanced Placement classes. Ms. Davis Gates mentioned that one of her children attends a private school for its superior athletic programs.

Mr. Martinez, the schools CEO, also has children in the district. He agrees with the objective of creating new programs to attract students back to under-enrolled schools, noting that Black students often travel the farthest across the city to find preferable schools.

The core of Mr. Martinez’s disagreement with the mayor lies in the funding strategies. While the mayor believes no funding options should be off-limits, Mr. Martinez contends that taking out a loan would replicate past mistakes, leaving the district in debt. He prefers to utilize property tax surpluses and seek increased state and federal investment.

Andrew Broy, president of the Illinois Network of Charter Schools, argues that instead of pouring resources into underperforming, low-enrollment schools, Chicago’s school leaders should support policies that enable more parents to choose the high-quality schools that suit their families’ needs.

He asserts that when the mayor and the teachers’ union president are closely allied, the interests of students and taxpayers are often overlooked.

“When both parties sit on the same side of the table, it’s the students and taxpayers who end up being marginalized,” he stated. “When they aren’t represented, they become the ones who are sacrificed.”

In the 1990s and early 2000s, Chicago, along with several other cities, shifted from elected school boards to mayoral control as part of a national movement aimed at improving accountability in public education. However, the academic and political results have been mixed. In 2021, Illinois Gov. JB Pritzker, a Democrat, enacted a law to transition Chicago back to an elected school board. With the first election for new board members approaching, both the union and its critics from the charter school community are investing heavily in direct mail campaigns.

Union supporters have accused their Democratic opponents of adopting a Trump-like agenda. Meanwhile, charter school advocates are pushing back against Mr. Johnson’s commitment to prioritize traditional neighborhood schools over charter schools, magnet schools, and selective enrollment options.

The union has long viewed an elected board as a way to influence governance. However, this shift to elections also opens the door for its opponents to gain representation.

Even some members of the Chicago City Council who lean left are growing skeptical of the mayor’s budget strategy, concerned about accumulating new debt when the district cannot meet its existing pension obligations.

City Council member Andre Vasquez noted that, like the mayor, he entered public office with a background in progressive activism. However, he argued that the two roles are fundamentally different.

“Many of us are accustomed to holding up picket signs,” he remarked. “Now, we must deliver tangible results. It quickly becomes clear that the reality is far more nuanced.”