The most recent manifestation of a new "Great Game," or a resurgence of interest in the geopolitical competition taking place in the Caucasus, occurred in August 2008 when Russia invaded and occupied parts of the Republic of Georgia. Russia's invasion, the first use of force outside its territory since the collapse of the Soviet Union in 1991, has forced a reassessment of U.S. and NATO strategy toward Russia and its relationship with the Republic of Georgia. The United States and NATO have yet to develop a new strategy that balances their enlargement policy of supporting Georgian sovereignty and independence with concerns about growing Russian security interests in the region. The main purpose of this thesis is to examine Georgia's national security dilemmas and explain the principal components of U.S. engagement policies designed to manage its strategic predicament. This thesis examines whether these engagement policies contribute to U.S. and NATO interests, bring greater stability to the region, and enhance European security. The study also analyzes how U.S. engagement in Georgia affects Georgian and Russian interests and explores the implications for U.S.-Russian relations in terms of a new "Great Game" of geopolitical competition in the region.