President Donald Trump delivers the Memorial Day Address at the 157th National Memorial Day Observance at Arlington National Cemetery, Monday, May 26, 2025, in Arlington, Va., as Vice President JD Vance and Secretary of Defense Pete Hegseth, right, look on (AP Photo/Julia Demaree Nikhinson).
A federal judge in Manhattan has ordered the Trump administration to reveal its justification for fatal attacks on boats in the Caribbean.
In a 66-page ruling issued Wednesday, U.S. District Judge Paul Engelmayer, a Barack Obama appointee, rejected numerous rationales advanced by the U.S. Department of Justice for keeping an Office of Legal Counsel (OLC) memo on the subject under wraps.
In August 2025, operating on a presidential directive authorizing military force against “foreign criminal groups,” the Department of Defense (DOD) began attacking boats it claimed were trafficking drugs into the country. Some 234 people have been killed in those attacks while the government has not provided evidence conclusively proving its claims, according to the underlying lawsuit filed by the American Civil Liberties Union and other groups.
Litigation began in December 2025 after the ACLU filed a Freedom of Information Act (FOIA) request. In denying the request, and thus withholding the OLC memo in full, the DOD cited three separate exemptions to the nation’s premier government transparency law.
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Through motions practice, the Trump administration and the ACLU worked toward common ground on two of those exemptions, according to the ruling. In theory, these concessions would have allowed for a limited release of the OLC memo with redactions after the document was reviewed by the judge.
The government, however, said one of those three exemptions meant they could still withhold the OLC memo in full, by citing privilege.
Now, on cross-motions for summary judgment, Engelmayer has found that privilege claim is simply not enough — at least not now.
The court cites the primacy of the OLC memo in the administration’s defense, however factually limited, of the boat strikes.
“[I]n public statements regarding the legality of the boat strikes, DOD and Administration officials have relied exclusively on the OLC Memo as defining the parameters of their authority to undertake these strikes,” the opinion and order reads. “They have not identified any other document (by OLC or otherwise) that does so, or that sets out the legal basis for the strikes. Nor, during this litigation, has either DOJ or DOD identified any alternative written guidance on this point.”
The parties do not dispute that “portions” of the OLC memo are likely properly withheld for national security and statutory reasons, the judge explains. The only real area of dispute is the underlying legal analysis, the court notes. And that analysis is what the ACLU is intent on making public.
Engelmayer points out that a DOJ attorney even “acknowledged at argument, although that legal analysis may embed facts or factual premises that implicate [national security and statutory exemptions] and require redaction, the balance likely could not be withheld based on those exemptions.”
To that end, the court found that typical notions of privilege — like the attorney-client privilege and the deliberative process privilege — simply do not apply to the OLC memo because the Trump administration has developed the memo to a sufficient point that it is relied on as “working law.”
“[T]he assembled record compellingly supports the finding that DOD—the agency that asserts disclosure authority over the Memo—has treated the Memo as its effective law and policy governing the boat strikes,” the judge explains.
The court elaborates:
[O]ther components of the Administration, including the White House, have held out the Memo in a similar manner. Under the standards set out by the Second Circuit, DOD has both expressly adopted the Memo and incorporated it by reference, so as to make it functionally binding and hence, “working law.”
DOD’s treatment of the Memo, in fact, tracks nearly every factor the Second Circuit has identified to gauge whether a document constitutes an agency’s working law[.]
Explaining the “working law” doctrine, Engelmayer cites precedent that rejects the idea of an agency using “a body of secret law which it is actually applying in its dealings with the public but which it is attempting to protect behind a label.”
While rejecting two of the government’s key rationales for invoking privilege, the court stopped short of ordering the Trump administration to release the OLC opinion. The judge ruled that he needs to review the document behind closed doors before making a final decision on disclosure.
“[T]he Court rejects the privilege claim with respect to two of the three privileges the agencies invoke (the deliberative process and attorney-client privileges),” the opinion and order reads. “But the existing record does not permit the Court to reliably resolve whether the agencies have waived their right to invoke the third (the presidential communications privilege). The Court accordingly orders the agencies to furnish information to enable it to resolve that question.”
The post Judge rubbishes ‘secret law’ and rejects Trump admin excuses for withholding OLC memo on fatal boat strikes in the Caribbean, court will review behind closed doors first appeared on Law & Crime.
