This paper is an analysis of the policies of global and regional actors in the South Caucasus for the past 25 years. This paper will look at each of these actors – the US and NATO, the EU, Russia, Turkey, and Iran – to analyze the web of overlapping or conflicting interests and patterns of influence and affiliation. This analysis is used to then propose a rethinking of policies of all five actors with implications for the countries of the South Caucasus and the conflict context. This will be done with the vision of increasing the fraction of shared interests and decreasing the confrontation of interests and the conflict potential in the region.