The article tracks the development of U.S. efforts to establish a presence and influence in the Central Asian and Caucasian regions in the post-Cold War era, as well as the Russian responses to those efforts-responses that, by spring 2009, appeared to have successfully warded off the challenge, but only a few months later seemed less effective. The argument will be developed in five stages. We will first survey the impact of the demise of the Soviet Union on Moscow's foreign policy, including its ability to establish and determine what it viewed as its key interests. We will then examine the efforts of the leaders of the post-Soviet states of the greater Caspian region to balance their dependence on Moscow with expanded economic, political and security links with states from outside the region. This will lead to a third issue, namely early U.S. efforts to establish contacts with and influence in the greater Caspian region as part of a broader policy of taking advantage of what many at the time viewed as the permanent demise of Russia as a major power. The fourth segment of the argument will outline the return of Russia as a major actor during the presidency of Vladimir Putin and the overall deterioration of Russian-U.S. relations. The final section of the narrative will track the recent tensions in U.S. relations with key Central Asian states and the apparent success-at least partial and possibly for the foreseeable future-of the Russians' efforts to reestablish themselves as the dominant external influence throughout the region. Included in this assessment, of course, will be a discussion of the interests of local political elites and the various ways in which those interests impact the new ‘Great Game’ for major power influence in the region. In many respects the expanded competition among large external states for a political role in the region has strengthened the ability of some of the regional states to play the great powers off against one another.