This chapter discusses Greece’s ‘Ostpolitik’ and the extent to which its aspirations supported or contradicted Western Cold War strategies. Karamanlis’ ‘Ostpolitik’ was a dynamic policy that gradually evolved from a—classic in Greek strategic tradition—move to improve relations with its neighbouring Socialist countries in order to counterbalance Turkey, into a refined strategy with the aspiration to actively contribute to East-West relations. Combining great ambitions with modest expectations, Karamanlis’ Balkan initiatives put Greece at the centre of intra-Balkan détente, but the practical results were limited. However, Greek policymakers were too pragmatic to expect impressive results; their primary objectives were to improve the political climate in the region, thereby reducing the likelihood of conflict, and at the same time, prove to the West that Greece was able to formulate a strategy essentially supportive of Western interests in the area. In this respect, Greece’s détente policy could only buttress the country’s Western orientation. In fact, Karamanlis’ ‘Ostpolitik’ and ‘Westpolitik’ were closely interconnected and mutually reinforcing.