The courts were doing brisk business on Thursday as an avalanche of orders came rolling out — many of them in cases involving the Department of Education. I am not going to lie, the fact that all of these semi-related rulings in multiple different jurisdictions (D.C., Maryland, New Hampshire) came out on the same day had me scratching my head and wondering at what game was afoot, until the light bulb finally went off: Today was the deadline by which state educational agencies needed to certify their compliance with the “Dear Colleague” letter issued by the ED in February.
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I feel better now that I figured that out — not better about all the rulings, mind you; just better that the timing at least makes sense. Something else that doesn’t quite make sense, however, is the administration’s decision to dismiss its appeal in the State of California case (pending in Massachusetts, mind you — there are multiple state plaintiffs). That’s one in which the Supreme Court actually granted a stay pending disposition of the appeal, so I’m not sure what the strategy is there.
But it wasn’t just ED-related cases in the spotlight today. There was election integrity, funding of sanctuary cities and states, OMB funding pauses, immigration — and pretty much none of these rulings went the administration’s way today. (And, for the record, several of the judges issuing them are Trump appointees.) Of course, none of these is the final say in any of the cases. Just one more speed bump along the way.
So, without further ado, here’s Thursday’s round-up:
- American Federation of Teachers v. Dept. of Education – 1:25-cv-00628 – (case challenging Dept. of Education “Dear Colleague” letter banning DEI-related programming) — Judge Stephanie Gallagher (Maryland) entered an order granting in part plaintiff’s motion for preliminary injunction and staying the administration’s implementation of its February 14 letter regarding DEI-related programming. In her 48-page memorandum opinion, Gallagher began by noting her ruling is not directed at the propriety of the policies themselves, but rather the way the administration is going about enacting them. Her order denies plaintiff’s motion as to the administration’s certification requirement (requiring states and school districts to affirmatively certify their compliance with ED’s interpretations of Title VI) because they didn’t challenge the certification requirement in their Amended Complaint.
- City and County of San Francisco v. Trump – 3:25-cv-01350 – (case challenging punishment of sanctuary cities and states) — Judge William Orrick III (Northern District of California) issued a preliminary injunction barring the administration from withholding, freezing, or conditioning funds on the basis of sanctuary jurisdiction status.
- League of United Latin American Citizens v. Trump – 1:25-cv-00946 – (case(s) challenging EO 14248 re: election integrity) — Judge Colleen Kollar-Kotelly issued a 120-page memorandum opinion in support of her order granting the plaintiffs a preliminary injunction, which prohibits the administration from giving effect to section 2(a) of the order (requiring proof of citizenship in the national mail voter registration form). Several related cases have been consolidated into this one. As to the related case filed by the DNC, her order prohibits the administration from giving effect to section 2(d) of the order (requiring the heads of agencies to “assess citizenship prior to providing a Federal voter registration form to enrollees of public assistance programs,” but denies some of the additional relief requested. For a more detailed rundown on this one, see: Federal Judge Blocks Part of Trump’s EO Requiring Proof of Citizenship to Vote.
- Mahdawi v. Trump – 2:25-cv-00389 – (case challenging removal/seeking habeas relief) — Judge Geoffrey Crawford (Vermont) entered an order extending his previously issued TRO (prohibiting the removal of Mahdawi from Vermont) for 90 days. (Mahdawi is/was a full-time undergraduate student at Columbia University, taken into custody in early April during his naturalization interview.)
- NAACP v. U.S. Dept. of Education – 1:25-cv-01120 – (case challenging Dept. of Education “Dear Colleague” letter banning DEI-related programming) — Judge Dabney Friedrich (D.C.) issued a preliminary injunction barring the administration from enforcing its recently issued certification requirement “under which state educational agencies must certify compliance with the Dear Colleague Letter by April 24 or lose federal funding.”
- National Council of Nonprofits v. OMB – 1:25-cv-00239 – (case challenging OMB memo re: temporary pause on grants, loans, assistance) — This one got a lot of attention when Judge Loren Alikhan initially entered a TRO. The administration has now appealed it to the D.C. Circuit.
- National Education Association v. U.S. Dept. of Education – 1:25-cv-00091 – (case challenging Dept. of Education “Dear Colleague” letter banning DEI-related programming) — As in the AFT v. ED case above, Judge Landya McCafferty (New Hampshire) issued a preliminary injunction barring the administration from implementing its February 14 letter regarding DEI-related programming.
- State of California v. U.S. Dept. of Education – 1:25-cv-10548 – (case challenging ban on DEIA initiatives) — So, this one’s interesting and a bit of a puzzler. SCOTUS has already entered a stay on this one, pending disposition in the 1st Circuit Court of Appeals…but the government has now voluntarily dismissed its appeal in the 1st Circuit. (Presumably, there’s a strategic reason for this, but at this point, I’m not clear on what that is.)
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I also want to mention something I’ve not really had an opportunity to study at length yet, and that is that some key documents were unsealed in the Alien Enemies Act case (J.A.V. v. Trump — this is the Texas offshoot of the J.G.G. case that was overseen by Judge Boasberg in D.C.). These are worth a deeper dive, and I aim to do just that once I get this published.
🚨🚨🚨BREAKING: Court unseals procedure for Alien Enemies Act removals, explaining notice & process. 2 key points: First, notice is given in native language, so did ACLU mislead court by focusing on written notice being only in English? 1/ pic.twitter.com/PTbIYKoNkv
— Margot Cleveland (@ProfMJCleveland) April 24, 2025
RELATED: New: Federal Judge Blocks Part of Trump’s EO Requiring Proof of Citizenship to Vote
Here We Go Again: Federal Judge Blocks Yet Another Key Trump Illegal Immigration Policy
And, of course, no Evening Docket would be complete without a sampling of the new suits filed that day:
- Harris County, Texas v. Robert F. Kennedy Jr. (challenging termination of grants)
- National Academy of Education v. Dept. of Education (challenging the cancellation of department contracts, reduction in force, and interference with the collection of education data under the Education Sciences Reform Act)
- National Family Planning and Reproductive Health Association v. Kennedy (challenging withholding of Title X grant money)
- Robert F. Kennedy Human Rights v. DHS (challenging closure of DHS oversight offices)
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You can check out prior installments of The Evening Docket series here.
Editor’s Note: President Trump is fighting to dismantle the Department of Education and ensure America’s kids get the education they deserve.
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