In the following communication Dimitrie Cantemir in the face of civilizational paradigm change, the authors try to examine from a different angle the actions of Dimitrie Cantemir (1673-1723) during his short reign in Moldova (1710-1711) and especially regarding his alliance with Peter I, Tsar of Russia (April 2/13, 1711). Starting from the fact that the Romanian scholar during his adolescence and youth had been formed as an intellectual and politician in the Orthodox cultural and spiritual environment from Moldova on the one hand and in that of the Islamic world and culture from Constantinople on the other, it can be assumed that he was acquainted both with the Christian European civilization and with the Arab-Turkish-Persian Oriental one. Throughout his entire literary creation as a historian, philosopher, musician, etc., Cantemir relied on representative scientific, cultural and religious values from both civilizational worlds. As for his political activity, both before and during his reign in Moldova, the Romanian prince understood that his homeland was included in the civilizational area of the Ottoman Empire, a circumstance that inhibited its development and affirmation on the international level. In accordance with the Biblical conception of the universal cycle of the four monarchies, which the erudite prince had embraced and further developed in a special study, Monarchiarum physica examinatio / A Natural Research of Monarchies, he considered that the unfolding political-military events at the crossroads of the two great civilizations, that of Europe and that of Islam, inevitably led to the collapse and disappearance of the Ottoman Empire as a historical anomaly. As a result, the baton of universal evolution would soon be taken over by the Northern monarchy, which was represented, according to D. Cantemir, by the Russian state. This system was used as the theoretical basis for the decision of the prince of Moldavia to break his relations with the Ottoman Gate and negotiate an alliance with the new rising European power. Thus, through such an action in these new circumstances, Cantemir was actually trying to break Moldova away from the area of Oriental civilization and place it de facto as a sovereign country in the new system of European international relations.