For centuries, American policymakers have likened Russia to a large, clumsy bear—a state whose power relies not on skill and appeal, but on brute force and the ability to intimidate. The unsuccessful Soviet invasion in Afghanistan seemed to confirm policymakers’ belief that Russia’s boorish foreign policy would fail among its Muslim neighbors to the south. However, this experience was an anomaly. Russia has since proved its agility in the Near East and outmaneuvered the United States. Moscow retained the loyalty of the Central Asian republics upon the Soviet Union’s disintegration. It prevailed in the Caucasus by cooperating with local Muslims. It turned the tide in the Syrian Civil War. And perhaps most remarkably, it drove a wedge between the U.S. and its formerly stalwart NATO ally, Turkey. While the clumsy bear caricature simplifies American planning, it leads to misguided policies. The past decades have shown that it is time for Washington to cast away this caricature and to study Russia with greater care and greater humility.