Trump’s bad day in court: President loses three times within 90 minutes on DEI, sanctuary cities and voter registration

Three federal judges blocked key parts of Donald Trump’s agenda in courtrooms across the country on Thursday, all within roughly 90 minutes of one another.

First, Trump’s executive orders targeting so-called “sanctuary cities” were deemed unconstitutional attempts to “coerce” local officials into enforcing the president’s immigration policies.

Next, the president’s attempts to withhold federal funding from schools that engage with diversity, equity and inclusion initiatives were labeled “textbook viewpoint discrimination” that likely violate the First Amendment.

And another judge blocked parts of the president’s sweeping executive order targeting election administration and voting rights, including a requirement that voter registration forms ask for proof of citizenship.

The latest setbacks to the Trump administration’s agenda, which has faced an avalanche of lawsuits, arrived in the middle of the president’s increasingly volatile position with a federal judiciary now confronting the administration’s routine defiance of the courts.

California District Judge William H. Orrick, who was appointed by Barack Obama, blocked the administration from withholding or freezing funding from 16 cities and counties it labeled “sanctuary jurisdictions,” landing a significant blow to Trump’s aggressive anti-immigration agenda.

In his order granting a preliminary injunction, Orrick cited Trump’s similar executive action from 2017 — which Orrick also blocked — that was found unconstitutional nationwide.

“Here we are again,” Orrick wrote Thursday. “Their well-founded fear of enforcement is even stronger than it was in 2017.”

One executive order directs Attorney General Pam Bondi and Homeland Security Secretary Kristi Noem to withhold federal funds to so-called “sanctuary” jurisdictions, while another order directs every federal agency to screen funds to state and local governments with “sanctuary’ policies” that “seek to shield illegal aliens from deportation.”

The orders likely violate the separation of powers and Fifth and Tenth Amendments, among other statutes, “because they impose coercive condition intended to commandeer local officials into enforcing federal immigration practices and law,” Orrick wrote.

In her 82-page order blocking a key part of Trump’s anti-DEI crusade in education, New Hampshire District Landya B. McCafferty, another Obama appointee, found that a letter from the Department of Education threatening federal funds “would cripple the operations of many educational institutions.”

“A professor runs afoul of the 2025 Letter if she expresses the view in her teaching that structural racism exists in America, but does not do so if she denies structural racism’s existence,” she wrote. “That is textbook viewpoint discrimination.”

The ruling, stemming from a lawsuit from the National Education Association and the American Civil Liberties Union, accused the administration of violating teachers’ due process and First Amendment rights.

She declined to issue a nationwide pause on the administration’s policy, limiting her ruling to schools that employ or contract with at least one member of the groups that sued.

Last month, Trump issued an executive order that voting rights advocates and legal scholars warn could disenfranchise millions of voters with sweeping changes to rules for election administration, including requirements that proof of citizenship be presented when registering.

Republicans in Congress introduced parallel legislation that passed in the House of Representatives earlier this month.

In her 120-page ruling, Washington, D.C. District Judge Colleen Kollar-Kotelly pumped the brakes on parts of Trump’s order.

“Our Constitution entrusts Congress and the States — not the President — with the authority to regulate federal elections,” wrote Kollar-Kotelly, who was appointed by Bill Clinton. “[N]o statutory delegation of authority to the Executive Branch permits the President to short-circuit Congress’s deliberative process by executive order.”

The president is “free to state his views” about policies he supports in Congress and across federal agencies, “but in this case, the President has done much more than state his views: He has issued an ‘Order’ directing that an independent commission ‘shall’ act to ‘require’ changes to an important document, the contents of which Congress has tightly regulated,” she added.

The Trump administration is facing dozens of legal challenges across the country in response to his executive orders and policy maneuvers that opponents argue are flatly unconstitutional or flying in the face of a system of checks and balances.

Several cases have reached the Supreme Court, including challenges to Trump’s attempt to revoke birthright citizenship for children of certain immigrants, mass firings of federal workers and agency officials, and deep cuts to foreign aid.