The perseverance of transactionalism in the global arena has deep implications for the security governance of the Black Sea region. In particular, for Turkey, the linkage between the Syria crisis with the Black Sea region due to Russia’s increasing presence in the Middle East has augmented its sense of insecurity. This paper thus attempts to explain and assess the factors driving Turkish strategic thinking as its carefully constructed strategy of being one of the two primus inter pares powers has failed to redress the current imbalance in favour of Russia.