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A previously secret memo on CIA involvement in drone killings is casting new doubt on whether the American government had any legal basis to prosecute Canada’s Omar Khadr for war crimes.

In fact, Khadr’s lawyers argue in new filings to the U.S. Court of Military Commission Review, the document by the Dept. of Justice emphatically rejects any such legal foundation, and say his convictions at Guantanamo Bay should be set aside immediately.

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The memo — produced in July 2010 in relation to the drone targeting of U.S. citizen Anwar Al-Awlaki — only came to light last month after a court ordered it disclosed in a hard-fought freedom of information case by the New York Times and the American Civil Liberties Union.

Specifically, the U.S. Dept. of Defence wanted to know whether CIA agents who operated drones — but who are not part of the military and do not wear uniforms — could be considered “unprivileged belligerents” and therefore be guilty potentially of war crimes.