In comparing Soviet era and Putin era foreign policies toward Arabia and the Gulf, a striking similarity emerges. In both eras, Moscow’s foreign policy has been characterized not so much by a grand design but by an opportunistic approach that seeks to have good relations simultaneously with both anti-Western and pro-Western actors, including those bitterly opposed to each other. At the heart of Moscow’s approach both then and now has been an effort by Moscow to balance between opposing parties and thereby derive benefits from both. Moscow’s logic in both eras seems to have been based on the expectation that governments and other actors will calculate that they are better off having good relations with Moscow despite its support for their adversaries since Moscow might well support those adversaries even more otherwise. This paper will show how Moscow has often pursued this “balancing between adversaries” approach in Arabia and the Gulf both in the Cold War when the Soviet Union was pursuing a revolutionary foreign policy and in the Putin era when Russia has been pursuing a status quo-oriented foreign policy. This will shed light on the enduring nature both of the foreign policy goals that Moscow pursues in this region and of the means by which it does so. I will argue, though, that Putin has been more successful at this approach than the Soviets were, but that it still involves important limitations and risks for Moscow. Moscow, of course, has not just pursued this balancing between adversaries strategy in Arabia and the Gulf, but has done so in other regions—or would certainly like to. Nor is Russia the only great power to have adopted this approach. The question being addressed here, though, is how successful Moscow has been in pursuing this approach in this one key region. I will first describe the similar balancing efforts that Moscow pursued (sometimes successfully and sometimes not) during both the Cold War and the Putin eras toward the countries of this region: Saudi Arabia; the smaller Arab Gulf states; the Yemen(s); and Iraq and Iran. I will then examine the broader similarities in Moscow’s foreign policies toward the region during both eras, and discuss their strengths and weaknesses then and now