Since achieving independence in 1991 with the fall of the Soviet Union, Georgia has become the most westward-oriented state in the Transcaucasus. The government in Tbilisi has departed from two centuries of union with Russia and vigorously pursued NATO membership as an avenue for restoration of its full sovereignty, domestic reform, economic development, and Euro-Atlantic integration. This first objective has been hampered by Russian-backed separatist regimes in Abkhazia and South Ossetia. Moscow has made its view clear that NATO encroachment into the South Caucasus poses a threat to its national security. Through overt threats, economic pressures, diplomatic control of the separatist regions, and covert attacks, the Kremlin has attempted to keep Georgia destabilized and dependent on Russia's good will. Its zero-sum, realist foreign policy opposes the institutional argument of enhancing security by diffusing democratic norms. This thesis will show how the degree to which Western governments are willing to confront coercive activity will largely determine the success or failure of Georgia's transition to a stable democracy.