Trump’s Anti-DEI Efforts Struggle Under Federal Judges’ Scrutiny
Jayne Vellinga’s work helping Black and Latina Chicago-area women prepare for construction careers ran into legal trouble when President Donald Trump ordered an end to federal funding for organizations promoting diversity, equity, and inclusion.
Trump’s third day into his second term last year brought letters from a US Department of Labor official telling Vellinga’s organization, Chicago Women in Trades, and dozens more like it to terminate all DEI-related activities that rely on federal dollars. Her group stood to lose about $1.7 million of its roughly $5 million annual budget.
But ending its pro-diversity mission wasn’t an acceptable option, Vellinga said. Like a wide range of other organizations, the Illinois group sued Trump, claiming his anti-DEI directives were unconstitutional.
In court, Chicago Women in Trades and other challengers found initial success. A federal judge ruled in April 2025 the government violated the group’s First Amendment rights by asking it to certify it doesn’t promote DEI. That ruling meant, at least temporarily pending the government’s appeal, Vellinga’s group could continue its mission and the Labor Department couldn’t cancel its grants.
“Our goal has always been to open up access to these nontraditional careers that offer high wages and opportunity for women,” Vellinga said.
While federal pressures have succeeded at discouraging diversity programs within some corporations, law firms, and universities, several groups that have fought in court to preserve DEI have found a variety of winning arguments. A handful of courts, like the federal court that heard Chicago Women in Trades’ case, determined Trump’s policies violated the First Amendment and were unconstitutionally vague, while others ruled the president’s moves violated the Constitution’s separation of powers.
In recent months, both Democratic and Republican appointed judges have ruled against Trump while finding the anti-DEI efforts lack clarity and legal authority when challenged in court, said Sabrina Talukder, senior counsel at the Lawyers’ Committee for Civil Rights Under Law, which represents Vellinga’s organization.
“It’s just been this resounding wave of pushing back,” she said.
Vellinga’s court victory underscores a challenge for Trump and his GOP allies’ efforts to erase decades-old diversity initiatives. While their political and regulatory pressure tactics have swayed many companies such as
A federal court in February dismissed the Missouri attorney general’s case claiming
Fighting the administration in court can be costly and risky for businesses.
But the rulings have been a boon to those groups that emerged victorious, at least temporarily. Even though the wins have been early stage—often preliminary injunctions that are pending appeals—they’ve forced GOP officials to retrench and find new legal arguments to support their initiatives.
‘Vagueness’ Debate
In recent litigation against Trump’s anti-DEI policies, various judges have taken issue with the administration’s failure to clearly define what illegal DEI looks like.
In court, Justice Department lawyers argued Trump’s executive orders challenged by Chicago Women in Trades and other organizations focus on illegal DEI and only require federal grant recipients and contractors to certify they don’t promote illegal discrimination.
The Fifth Amendment’s “vagueness doctrine has no bite because the provisions do not declare any new conduct unlawful,” the DOJ argued in a March 2025 court filing in the Chicago Women in Trades case.
But Judge Matthew F. Kennelly, a Clinton appointee, disagreed. He deemed the orders unconstitutionally vague and ruled they offered no guidance on what illegal DEI means and left it “entirely to the grantee’s imagination.”
Kennelly ruled “the government’s view of what is illegal in this regard has changed significantly with the new administration,” and yet Trump’s orders and the Justice Department’s legal briefs and arguments failed to define “how it has changed.”
In July, Judge William Glover Young, a Reagan appointee to the US District Court in Massachusetts, cited a lack of clarity when he ruled against the US Department of Health & Human Services’ cancellation of National Institutes of Health research funding linked to DEI and issues related to the LGBTQ+ community regarding initiatives such as health disparities and HIV.
The administration’s orders “set it up as some sort of boogeyman,” Young wrote, finding the NIH’s cancellation of whole categories of funding illegal under the Administrative Procedures Act.
Press secretary Emily Hilliard told Bloomberg Law the agency “stands by its decision” to end the funding.
“HHS is committed to ensuring that taxpayer dollars support programs rooted in evidence-based practices, not driven by divisive DEI mandates or gender ideology,” she said.
It’s possible the administration is intentionally keeping its definitions vague, with the goal of applying maximum pressure outside of court to discourage DEI efforts, said Joshua S. Roffman, a human resources compliance attorney at Roffman Horvitz PLC.
“You have courts questioning,” Roffman said, “you haven’t defined what unlawful DEI is. And they probably don’t want courts to pin them down it.”
A March 26 executive order doubled down on using federal contract language to bar businesses and organizations from discriminatory DEI by referencing “disparate treatment.” Trump’s initial anti-DEI orders early in his second term didn’t mention that more tangible legal standard, which courts have long used in determining whether an employment decision violates the 1964 Civil Rights Act.
That latest order shows an effort by the administration to clarify illegal DEI and put it on sturdier legal footing, said Judge Glock, research director and senior fellow at the Manhattan Institute.
The order and related guidance, Glock said, “seem to be focusing on discriminatory practices, bringing them closer to the intention and language of the Civil Rights Act.”
Jacob Scott, an attorney who advises government contractors at Smith Currie Oles, said the order still leaves the administration with broad discretion in how it enforces the restrictions.
“Certainly, as somebody who would have an interest in defending against a charge like this, it doesn’t give the type of specificity that I would hope to see, given the severity of the potential impacts to contractors in a prosecution or debarment situation,” he said.
DOJ spokesperson Natalie Baldassarre said the agency will continue to carry out the administration’s plans of curtailing DEI efforts that consider protected traits like race.
“As reaffirmed numerous times by the Supreme Court, discriminating against any individual based on any protected characteristic is unlawful,” she said. “The Department of Justice has not, and will not, stand idly by as recipients of federal funds violate federal civil rights laws, and our work to protect ALL Americans will continue no matter the wishful thinking of so-called legal ‘experts’.”
Tangible Harm
Courts’ demands for specificity hamper government officials both when defending DEI restrictions and dismantling diversity programs.
Missouri’s Republican attorney general encountered the issue when a federal judge found the AG failed to identify any individuals harmed by Starbucks’ diversity practices in hiring, training, mentorship, and promotions.
The attorney general alleged that Starbucks linked race- and gender-based hiring quotas to executive compensation. But the court determined the lawsuit lacked sufficient evidence that Starbucks used its DEI efforts to create a more female, and less White, workforce.
“It would be a far leap for the court to infer that the conclusory allegations specific to Missouri establish that any portion of the state’s population has been harmed by the defendant’s actions,” added Judge John A. Ross of the US District Court for the Eastern District of Missouri, an Obama appointee.
Starbucks maintained in court filings that its diversity policies don’t exclude in a way that would violate federal anti-bias laws, such as Title VII of the 1964 Civil Rights Act. Its race- and gender-based hiring policies were aspirational, not strict quotas, it said.
The AG’s office has appealed the ruling. Stephanie Whitaker, a Missouri AG spokesperson, said the office will continue pursuing cases where companies have race-and-sex-based hiring practices in violation of state law. Starbucks didn’t respond to requests for comment.
Finding White male plaintiffs who can bring allegations that DEI programs have harmed them has also proven challenging, given they aren’t historically prime filers of discrimination suits, legal observers say.
This could explain why EEOC and Justice Department officials during the Trump administration have used social media to encourage White men to file workplace bias claims, said Vicky Slade, an attorney with Davis Wright Tremaine LLP.
On Tuesday, the EEOC sued The New York Times on behalf of an unidentified White, male editor who alleged his race and sex factored into the newspaper’s decision not to consider him for a promotion. The publication’s diversity goals, according to the complaint filed in the Southern District of New York, influenced its decision not to advance him to a final interview panel for a promotion.
The Times spokesperson said the newspaper’s promotions are “merit based” and the paper “categorically rejects the politically motivated allegations brought by the Trump administration’s EEOC.”
Meanwhile, DEI supporters also faced difficulty alleging specific harms to satisfy courts. In February, the Fourth Circuit overturned an injunction blocking portions of Trump’s executive orders in a case brought by an association of diversity officers in higher education, university professors, and the City of Baltimore.
The Richmond, Va. appeals court, rejected the diversity group’s argument that the orders ran afoul of their constitutional rights to speak freely on diversity issues and to have due process before any government enforcement action, including clear notice of what’s required of them. Judge Albert Diaz, an Obama appointee, said the orders weren’t unconstitutional because they served as instructions to federal agencies rather than legal requirements imposed directly on the officers.
There’s no shortage of chances to continue challenging the Trump administration’s anti-DEI policies, according to Democracy Forward, which served as legal counsel to the National Association of Diversity Officers and many plaintiffs in similar lawsuits. The group joined an April 20 lawsuit against Trump’s latest DEI executive order.
“A range of the President’s initiatives that weaponized federal funding to target equity efforts have been found by federal courts in early stages of litigation to be unlawful,” said Democracy Forward CEO Skye Perryman. “We will continue to use every legal tool available to hold this administration accountable.”
‘Whack-a-Mole’
Several challengers to Trump’s anti-DEI campaign are waiting to see how federal appeals courts will rule on their claims. Even if appeals courts largely agree that most diversity efforts are legal, the administration has used other means to eliminate DEI, such as with merger approvals or withholding regulatory licenses.
T-Mobile US Inc., which has two merger deals awaiting the Federal Communications Commission’s approval, said it dropped its DEI policies to appease the agency’s chair, who publicly stated that proposed acquisitions wouldn’t otherwise be approved. That decision follows Verizon Communications Inc.'s acquisition of Frontier Communications Parent Inc. after agreeing to FCC demands to roll back DEI.
“It’s sort of whack-a-mole,” attorney Slade said. “You think that you’ve successfully challenged one way that they’re coming for this program and then something else pops up.”
Such was the case for
IBM didn’t respond to requests for comment on the settlement.
Meanwhile, a former IBM vice president Monday accused the company of illegally firing five of its seven Black executives last year “to appease the Trump administration, and to remain favored by the Defense Department and other government agencies” that have contracts with the company in response to federal anti-DEI sentiments.
Annette Brooks, who worked at IBM for 26 years, said in her New York federal court complaint that she was one of three Black vice presidents fired simultaneously in January 2025.
Through a statement released by her attorney, Pamela Keith of the Center for Employment Justice, Brooks described the lawsuit as “a difficult step but necessary to address the pattern of discrimination towards me and Black executives at IBM.”
IBM spokesperson Miki Carver denied the allegations and said race played no role in Brooks’s termination.
In some instances, legal scrutiny inside the courtroom has forced the administration to back down from its anti-DEI initiatives.
In January, the Department of Education told the Fourth Circuit it withdrew its letter threatening funding cuts for educational institutions that maintain DEI programs or teach topics like critical race theory.
That decision came after multiple judges, including Stephanie A. Gallagher, a 2019 Trump appointee to a federal court in Maryland, found the letter’s “vague language and threats of enforcement” to be unconstitutional.
“The government did not merely remind educators that discrimination is illegal: it initiated a sea change in how the Department of Education regulates educational practices and classroom conduct, causing millions of educators to reasonably fear that their lawful, and even beneficial, speech might cause them or their schools to be punished,” Gallagher wrote.
Meanwhile, Vellinga and the Chicago Women in Trades continue to focus on training minority women for construction careers.
Despite a court injunction that prevented immediate cancellation of the Chicago organization’s grants, three grants expired and two others are scheduled to end later this year. The government’s appeal of that injunction remains pending. Vellinga said she hopes to replace a portion of the group’s funding with private donations, but still expects its budget will shrink to $3.5 million next year, a 30% drop since Biden’s final year in the White House.
“Being a woman in the construction trades is not at all an easy thing to do,” Vellinga said. “To have them dismissed as being less qualified or that they’re all DEI hires or some crap like that when people have worked so hard—worked harder, not less hard in order to get the same sort of opportunities—it’s so disrespectful and so very difficult to not challenge it.”
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