This article discusses the triangle of competition between Russia and the USA over three members of the Organization for Democracy and Economic Development, GUAM: Azerbaijan, Georgia, and Ukraine. The first of three sections analyze how Russian leaders and politicians have, since 1991, prioritized the reintegration of the former Soviet space over nation-building in the Russian Federation. Russian officials and politicians have always viewed the former USSR, the Commonwealth of Independent States (CIS) and Eurasia as “Russia’s exclusive sphere of influence”. Russia has supported separatism and manufactured frozen conflicts, recognized the “independence” of separatist regions, and annexed neighbouring territories in countries that have stepped in a direction contrary to Russia’s regional interests in Eurasia. The second section focuses on Ukraine and GUAM members Azerbaijan and Georgia, which have prioritized building nation states over joining integration projects in the post-Soviet space and have implemented independent or pro-Western security policies. The third section analyses US security policy towards Eurasia and the South Caucasus under assertive (Bill Clinton, George W. Bush) and indifferent (Baack Obama, Donald Trump) presidents. This section discusses policies that US President Joseph Biden could pursue to revive the US as a security actor in partnership with Turkey towards Eurasia and the South Caucasus in pursuit of what US National Security Adviser Zbigniew Brzezinski described as “geopolitical pluralism” in Eurasia.