Chicago is a testing ground for some of the left’s biggest ideas about race and education. School systems in the city and nearby suburbs are pushing to hire more Black male teachers, add more Black history and train teachers in concepts like white privilege.
Some of those policies have a strong record of improving student learning, while others lack much track record.
But for the Trump administration, all of it could be against the law.
Now, school districts with programs aimed at lifting up Black students, and others, are finding themselves legally vulnerable. The White House is pursuing a reversal of the federal government’s traditional role on race and schools, going after what it calls “illegal DEI,” or diversity, equity and inclusion. The administration is using the Education Department’s Office for Civil Rights, which was established to protect racial and ethnic minority groups, to try to end programs meant to help some of those same students.
Through executive orders, investigations and threats to cut funding, the government has put what was once a bipartisan movement to address the legacy of slavery and racism on the defensive. Even Republican-leaning states such as Florida and Mississippi have teacher recruitment programs intended, in part, to diversify the workforce — an idea the administration has called illegal affirmative action.
For 20 years, research has demonstrated that students perform better academically when their teachers share elements of their racial, cultural or linguistic identity. And a broad range of social scientists, policymakers and parents have raised concerns about the lack of diverse male role models, as a response to boys’ struggles with academics and mental health.
But over the past decade, many conservatives began to push more forcefully for colorblind policies. Now, Trump administration lawyers are arguing that when school leaders direct resources to racial groups that remain behind, they discriminate against those that have traditionally been ahead.
Nowhere is the potential impact of this reversal starker than in Illinois. The Education Department has announced civil rights investigations into two of the state’s most prominent school systems, in Chicago and in the nearby college town of Evanston, accusing them of breaking the law by focusing school improvement efforts on nonwhite children.
Conservatives hope the cases against the two districts will set precedents that can reach into schools and other institutions nationally.
Kimberly Hermann, president of Southeastern Legal Foundation, the conservative group that filed a lawsuit and federal complaint against the school district in Evanston, acknowledged that many education leaders believe race-conscious programs will help disadvantaged students.
“Sometimes you can have a noble goal,” she said, “but you can’t implement it in a way that violates laws.”
‘Liberatory’ or ‘Illegal’
This fall, Chicago Public Schools will roll out what it calls the Black Student Success Plan. It calls for doubling the number of Black male teachers hired by 2029, reducing disciplinary actions against Black students, adding more Black history and enrolling more Black children in advanced courses.
Sarah Parshall Perry, vice president of Defending Education, a conservative legal group that filed a federal complaint against the plan, argued that by focusing so much on Black students, Chicago risked ignoring the needs of other groups, like Hispanic students. Black children make up 34% of the district’s students, while Hispanic children account for nearly half.
“I think a lot of these schools are well intentioned but ill advised,” Perry said. “In their effort to level the playing field for one specific group, they have failed to account for the needs of all students.”
State data suggests Hispanic students score somewhat higher on standardized tests than Black students do, and are more likely to enroll in Advanced Placement classes. But both groups significantly lag Asian and white peers.
In an April statement announcing the investigation, Craig Trainor, acting assistant secretary for civil rights at the Education Department, said Chicago was reserving resources for “favored” students, and that the Trump administration “will not allow federal funds, provided for the benefit of all students, to be used in this pernicious and unlawful manner.”
The theory of the Black Student Success Plan is that efforts to assist Black children will help everyone. The district calls this approach “targeted universalism,” saying that “ambitious goals can be achieved by all students if we prioritize those who are furthest from opportunity.” It says the plan requires “liberatory thinking” to “disrupt systemic inequity.”
There is promising research on social studies courses that reflect students’ identities, showing improvements in grades and attendance.
North of Chicago, District 65, which oversees elementary and middle schools in the diverse suburbs of Evanston and Skokie, has pursued similar racial equity efforts for years. It offers an Afrocentric magnet program and enrolled all students in eighth-grade Algebra I, previously an advanced course where Black and Hispanic students were underrepresented.
But it is a separate set of practices — anti-racism training sessions for teachers — that have made the district a target of the Trump administration.
A white drama teacher in the school system, Stacy Deemar, has filed several legal complaints accusing her employer of creating a “racially charged environment,” in part by requiring staff members to participate in training focused on concepts such as white privilege and white fragility, sometimes in “affinity groups” segregated by race.
The Trump administration opened an investigation into the district in response to Deemar’s complaint. She is represented by the Southeastern Legal Foundation.
Supporters of anti-racism training have said it helps white people become aware of discriminatory beliefs and behavior, such as a teacher punishing a Black boy more harshly than a white boy for the same infraction. But some research suggests that the training can arouse white resentment and become counterproductive, sometimes even reinforcing racial stereotypes.
The district has reported a decrease in serious behavioral incidents, by about 50% over two years. And since 2021, the percentage of students meeting state standards in math and reading has grown. But there have also been challenges in math, with many of the district’s graduates having to retake algebra in high school.
District 65 declined to answer specific questions about its racial equity programs, saying it could not do so because of the continuing investigation. “The complaint misrepresents our district’s lawful and important professional learning and student-focused initiatives,” it said in a statement.
A Broadening Legal Battle
Regardless of whether racial equity programs work to improve student learning, the White House considers many of them illegal.
The administration cites Title VI of the Civil Rights Act, which seeks to prevent discrimination based on race, to argue that discussions of white privilege and structural racism violate the law by creating hostile environments filled with racial stereotypes. It calls single-race or single-sex discussion groups “segregationist activities.”
The administration has also put forth a more novel legal theory: that because the Supreme Court banned affirmative action in college admissions, no educational institution, at any level, may direct benefits toward any specific racial group.
A federal judge rejected many of those arguments in August, noting that there was no language in the 2023 affirmative action decision limiting the public school curriculum. She halted one of the administration’s attempts to withhold funding from schools and colleges with diversity and equity efforts, saying it violated free speech.
But the White House could appeal, and the question of whether public schools can remain race conscious is likely to go before the Supreme Court in the coming years. Several conservative justices have expressed an interest in taking up the subject.
Chicago Public Schools did not respond to questions about why the system was sticking by its racially targeted approach.
But the politics of education have changed with Trump in the White House. Democratic Party leaders, including Mayor Brandon Johnson of Chicago and Gov. JB Pritzker of Illinois, have reveled in confrontation with the president.
“The Trump administration has looked for any excuse to target Democrat-run cities across the country, and, particularly, cities run by Black mayors,” said Johnson, who has indicated the city would consider legal action if the federal government withheld education funding.
“There is nothing illegal,” he added, “about providing targeted support for Black students.”
This article originally appeared in The New York Times. © 2025 The New York Times
