The aim of this hypothesis is to compare the interrelatedness between the Phoenician, Greek and Latin alphabet and the Macedonian Cyrillic alphabet, based on new research challenges in exploring recently evidenced peculiarities in age and identity of literacy signs, found at various sites within the Republic of Macedonia. These findings on tomb stones, excavations and rock art engravings point to written signs, some of them as old as 9.000 years, others offering incredible assumptions for consequent alphabets. Some of the ancient signs discovered in the Republic of Macedonia date back some 40.000 B.C. (Vasil Iljov, Marija Gimbutas). This analysis particularly explores the missionary role of the Phoenician ruler Cadmus in his diffusion of Mediterranean written signs, later foundations for alphabetical systems. His trips took place around 2000 B.C. and included the famous ancient cultural and educational town of Ohrid, Kutmichevica (after the name of Cadmus), in the Republic of Macedonia, as well as other regions of the European civilization’s linguistic territories. The scientific facts in this paper encounter mythology on its way to the formation of alphabets and their impact upon actual and fundamental intercultural exchange and evolution of the European letters. The ancient assumptions related to the literacy missioner, the ruler Cadmos, led to the quest in this paper for distinctiveness and interaction between the Macedonian, Cyrillic alphabet, and the other Phoenician, Greek and Latin alphabets.