Judge Hits Pause on Trump Team’s DEI Crackdown, Signals Free Speech Concerns

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A federal judge in Chicago has temporarily halted part of the Trump administration’s aggressive move to strip diversity, equity, and inclusion (DEI) efforts from organizations that rely on federal labor grants.

In a two-week restraining order, U.S. District Judge Matthew Kennelly said the Labor Department cannot, for now, demand that grant recipients sign off on a pledge declaring they operate no DEI programs—even those entirely unrelated to their federal funding. The judge warned this certification mandate could violate free speech protections under the First Amendment.

Kennelly’s ruling marks a partial victory for Chicago Women in Trades (CWIT), a nonprofit training women for trades like carpentry and welding, which argued the new DEI restrictions would effectively silence their advocacy or force them to abandon core aspects of their mission. The judge agreed, warning that the rule could chill speech and create an atmosphere of “self-censorship.”

“The impact… is likely to result in self-censorship,” Kennelly wrote in his order, noting that even DEI programs outside the scope of federal contracts would be vulnerable under the Trump directive.

The judge also blocked the Labor Department from revoking CWIT’s funding under Trump’s January 21 executive order, which had ordered agencies to terminate so-called “equity-related grants.” However, this relief was limited to CWIT alone. Kennelly stopped short of issuing a nationwide injunction, cautioning that such sweeping rulings should be reserved for exceptional cases to avoid jurisdiction-shopping.

The Trump administration’s campaign to dismantle DEI initiatives—framed by its supporters as a push for neutrality and fairness—has sparked legal battles across the country. Just weeks earlier, a federal appeals court greenlit a temporary ban on DEI initiatives within federal agencies and private contractors, pending the outcome of broader litigation.

The Labor and Justice Departments have not yet commented on the ruling.

As the legal tug-of-war over DEI intensifies, Kennelly’s decision sets the stage for a broader showdown over how far the government can go in policing ideological commitments tied to public funding—and whether those boundaries clash with the Constitution itself.

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