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What do Kobe Bryant, Aristotle, and the continuing U.S. response to the terrorist attacks on September 11, 2001, have in common? President Barack Obama told the New Yorker in early 2014, in response to a question regarding the seeming resurgence of al Qaeda in Syria and Iraq, that “[t]he analogy we use around here sometimes, and I think is accurate, is if a jayvee team puts on Lakers uniforms that doesn’t make them Kobe Bryant.” As this example demonstrates, the Obama Administration and others, in reference to the legality of the use of armed force against al Qaeda and similar groups, have frequently employed an ancient tool of thought dating back to Aristotle—the use of analogies in reasoning. Reasoning by example, or making legal assessments by highlighting similarities and differences among examples, seems to dominate the Obama Administration’s discussions of the legality of its armed response to al Qaeda and its associates. This is reflected in the above Kobe Bryant example, as well as in high-ranking U.S. government lawyers’ repeated use of the U.S. shoot-down of Japanese Admiral Yamamoto’s plane over the Pacific Ocean during World War II to legally justify today’s lethal targeting of individual al Qaeda members. Yet this method of analogical legal reasoning is not restricted to U.S. government lawyers and other officials when arguing the legality of modern drone strikes. It is a hallmark of legal debates, inside and outside of government, regarding the use of military force against non-state terrorist groups in general since September 11, 2001. This Article’s primary point is simply that the inherent vagueness in international law and its interpretive methodologies, and the opaqueness particularly resident in the international legal regulation of the use of force against non-state actors, encourage resort to legal interpretation by analogy when addressing post-9/11 law of war issues. Normatively, this Article warns that such an approach should be more transparent and that its use should be infused with greater methodological rigor. This scene-setting discussion leaves substantive analysis of discrete law of war analogies and process recommendations to a future law review article.