A federal judge in Manhattan has ordered the Trump administration to lay out its legal reasoning behind a string of deadly boat strikes in the Caribbean, rejecting the government’s attempt to keep that rationale sealed from public view.
In a 66-page ruling issued Wednesday, U.S. District Judge Paul Engelmayer, an Obama appointee, shot down most of the arguments the Department of Justice had used to justify withholding an Office of Legal Counsel memo tied to the strikes.
The strikes date back to August 2025, when the Department of Defense began targeting boats it said were smuggling drugs into the United States, acting under a presidential directive that authorized military force against what the administration called “foreign criminal groups.” According to the lawsuit brought by the ACLU and other organizations, roughly 234 people have died in these operations, even though the government has never produced evidence that conclusively backs up its trafficking claims.
The legal fight kicked off in December 2025 after the ACLU submitted a Freedom of Information Act request. The Department of Defense denied it outright, withholding the OLC memo in full and pointing to three separate FOIA exemptions as justification.
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As the case moved through motions, the administration and the ACLU found some common ground on two of those three exemptions, the ruling notes. That partial agreement could have paved the way for releasing a redacted version of the memo once the judge had a chance to review it privately.
But the government held firm on the third exemption, arguing that various forms of privilege still justified withholding the memo in its entirety.
Ruling on cross-motions for summary judgment, Engelmayer decided that argument doesn’t hold up, at least not yet.
Central to his reasoning is how heavily the administration itself has leaned on the OLC memo to defend the strikes, even in its limited public statements.
“[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 states. “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.”
Both sides agree that some portions of the memo are likely exempt on national security or statutory grounds, the judge notes. The real fight is over the legal analysis itself, which is precisely what the ACLU wants made public.
Engelmayer points out that a DOJ attorney conceded during arguments that while the legal analysis might touch on facts tied to those narrower exemptions, requiring some redactions, the bulk of it likely couldn’t be shielded on those grounds alone.
Given that, the court found that standard privilege protections, such as attorney-client privilege and deliberative process privilege, don’t apply here, since the administration has treated the memo less like internal deliberation and more like settled policy, or what courts call “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 writes.
He goes further, noting that other parts of the administration, including the White House, have pointed to the memo the same way. Under Second Circuit standards, Engelmayer finds that DOD has both adopted the memo outright and folded it into its operations by reference, effectively making it binding, and therefore “working law.” The memo’s treatment, he adds, checks nearly every box the appeals court has laid out for identifying an agency’s working law.
In explaining the working law doctrine, Engelmayer cites earlier case law warning against agencies relying on what amounts to secret law, rules they actually apply to the public while hiding behind a legal label.
Still, even after knocking down two of the government’s three privilege arguments, the judge stopped short of ordering the memo released outright. He said he first needs to examine the document himself, privately, before deciding what should ultimately become public.
“[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 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.”
