Federal Judge Paul Engelmayer has ordered the Trump administration to disclose its legal justification for fatal attacks on Caribbean boats, rejecting key claims of privilege that the Department of Defense used to withhold the Office of Legal Counsel memo. The ruling, issued Wednesday, stems from a Freedom of Information Act lawsuit filed by the American Civil Liberties Union and other groups challenging the military operations.
The Military Operations and Legal Challenge
In August 2025, the Department of Defense began targeting boats it claimed were trafficking drugs into the region under a presidential directive authorizing force against foreign criminal groups. According to the lawsuit, approximately 234 people have been killed in these attacks, though the government has not provided conclusive evidence supporting its claims. The ACLU filed a FOIA request in December 2025 seeking the OLC memo, which the DOD denied in full by citing three separate exemptions to the transparency law.
Through motions practice, both sides reached agreement on two of the three exemptions, potentially allowing for a redacted release of the memo after judicial review. However, the government maintained that one exemption-privilege-justified withholding the entire document. Engelmayer rejected this claim, finding that typical notions of privilege – like the attorney-client privilege and the deliberative process privilege – 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”.
Court’s Rejection of Privilege Claims
The court emphasized that DOD and administration officials have publicly relied exclusively on the OLC memo to justify the boat strikes, with no other written guidance identified during litigation. “[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 ruling states. White House and other administration components have similarly treated the memo as binding policy.
Engelmayer explained that the memo’s adoption aligns with the Second Circuit’s criteria for determining whether a document constitutes an agency’s working law. The judge cited precedent rejecting the notion of agencies operating under secret laws while claiming public application. While acknowledging that portions of the memo may properly remain classified for national security reasons, he noted that the core legal analysis, the ACLU’s primary interest, could require disclosure with appropriate redactions.
Procedural Next Steps and Remaining Issues
The ruling does not mandate immediate release of the OLC opinion. Instead, the judge ruled that he needs to review the document behind closed doors before making a final decision on disclosure, and orders the agencies to furnish information to enable resolution of whether the presidential communications privilege-distinct from the rejected deliberative process and attorney-client privileges-has been waived. This exemption protects communications between the president and advisors, and the court determined the existing record is insufficient to decide this question definitively.
The government’s argument centered on the memo representing confidential legal advice embedded within presidential decision-making.
Judge’s Ruling Details and DOJ’s Position on Redaction
U.S. District Judge Paul Engelmayer, appointed by President Barack Obama, issued a 66-page ruling rejecting numerous rationales advanced by the Department of Justice for maintaining the Office of Legal Counsel memo under seal. The decision addressed the legal basis for withholding the document from public disclosure.
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.”
