WASHINGTON -- A federal judge in Manhattan refused on Wednesday to require the Justice Department to disclose a memorandum providing the legal justification for the targeted killing of a United States citizen, Anwar al-Awlaki, who died in a drone strike in Yemen in 2011.
The ruling, by Judge Colleen McMahon, was marked by skepticism about the antiterrorist program that targeted him, and frustration with her own role in keeping the legal rationale for it secret.
"I can find no way around the thicket of laws and precedents that effectively allow the executive branch of our government to proclaim as perfectly lawful certain actions that seem on their face incompatible with our Constitution and laws while keeping the reasons for their conclusion a secret," she wrote.
"The Alice-in-Wonderland nature of this pronouncement is not lost on me," Judge McMahon wrote, adding that she was operating in a legal environment that amounted to "a veritable Catch-22."
A lawsuit for the memorandum and related materials was filed under the Freedom of Information Act by The New York Times and two of its reporters, Charlie Savage and Scott Shane. Wednesday's decision also rejected a broader request under the act from the American Civil Liberties Union.
David E. McCraw, a lawyer for The Times, said the paper would appeal.
"We began this litigation because we believed our readers deserved to know more about the U.S. government's legal position on the use of targeted killings against persons having ties to terrorism, including U.S. citizens," Mr. McCraw said. "Judge McMahon's decision speaks eloquently and at length to the serious legal questions raised by the targeted-killing program and to why in a democracy the government should be addressing those questions openly and fully."
Jameel Jaffer, a lawyer with the A.C.L.U., said his group also planned to appeal. "This ruling," he said, "denies the public access to crucial information about the government's extrajudicial killing of U.S. citizens and also effectively greenlights its practice of making selective and self-serving disclosures."
A Justice Department spokesman said only that lawyers there were reviewing the decision.
Judge McMahon's opinion included an overview of what she called "an extensive public relations campaign" by various government officials about the American role in the killing of Mr. Awlaki and the circumstances under which the government considers targeted killings, including of its citizens, to be lawful. The Times and the A.C.L.U. argued that the government had waived the right to withhold its legal rationale by discussing the program extensively in public.
(Samir Khan, a naturalized American citizen who lived at times on Long Island and in North Carolina, was also killed in the strike, on Sept. 30, 2011. Another strike two weeks later killed a group of people including Mr. Awlaki's 16-year-old son, Abdulrahman al-Awlaki, who was born in Colorado.)
President Obama and Defense Secretary Leon E. Panetta both acknowledged that the United States played a role in the elder Mr. Awlaki's death, Judge McMahon wrote. But she focused in particular on a March speech by Attorney General Eric H. Holder Jr. at Northwestern University.
When United States citizens are targeted for killing, Mr. Holder said, the Constitution's due process protections apply. But due process does not require "judicial process," he added.
On the one hand, Judge McMahon wrote, "the speech constitutes a sort of road map of the decision-making process that the government goes through before deciding to 'exterminate' someone 'with extreme prejudice.' " On the other hand, the speech was "a far cry from a legal research memorandum."
The government's public comments were as a whole "cryptic and imprecise," Judge McMahon said, and were thus insufficient to overcome exemptions in the freedom of information law for classified materials and internal government deliberations.
"It lies beyond the power of this court to conclude that a document has been improperly classified," she wrote, rejecting the argument that legal analysis may not be classified.
Judge McMahon said she had not reviewed the withheld documents, including the one at the heart of the case, which was prepared by the Justice Department's Office of Legal Counsel. She said the memorandum must contain more detailed legal analysis than the broad statements in Mr. Holder's speech "unless standards at O.L.C. have slipped dramatically."
The Times published an account of the Office of Legal Counsel memorandum in October 2011, citing people who had read it.
Even as she ruled against the plaintiffs, the judge wrote that the public should be allowed to judge whether the administration's analysis holds water.
"More fulsome disclosure of the legal reasoning on which the administration relies to justify the targeted killing of individuals, including United States citizens, far from any recognizable 'hot' field of battle, would allow for intelligent discussion and assessment of a tactic that (like torture before it) remains hotly debated," she wrote.
This article originally appeared in The New York Times.