Currently, the Eastern Mediterranean Sea is brewing as a region of potential conflict rather than cooperation due to continuous geopolitical and geo-economic competition among various actors, not only at the national level but also at regional and strategic levels. Turkey, having one of the longest coasts in the Mediterranean Sea, and the Turkish Republic of Northern Cyprus (TRNC) are facing both military-naval challenges and new U.S.-based alignments that aim to prevent both the TRNC and Ankara from exercising their legal rights in the Mediterranean Sea. In this challenging environment, Turkey continues to be active diplomatically while also feeling obliged to uphold its legal rights by conducting searches for hydro-carbon energy by means of newly acquired seismic drilling vessels – usually under the protection of its upgraded naval fleet. This analysis seeks to explain why Western/U.S. behavior is building confrontational alignments aimed at excluding both Turkey and the TRNC from the ongoing Mediterranean balance of power game, and why President Trump's current shortsighted Mediterranean strategy is doomed to fail in bringing peace to the Mediterranean region in general.