In the following study Dimitrie Cantemir about the Metropolitan Dosoftei of Moldavia, it is shown that the erudite prince met the Metropolitan Dosoftei (1624-1693) when he was a teenager and when his father, Constantin Cantemir (1624-1693) was the ruler of the Moldavian Principality (16851693), leading to the fact that these three important personalities had interesting intersections in their activities both during the times of peace and war after the entry of the Polish king Jan Sobieski with his army into Moldova. Some of these resonant moments in history are reflected by Dimitrie Cantemir through the lens of his own impressions, as well as of Constantin vodă Cantemir’s relationships and attitude towards Dosoftei’s actions when the Polish army entered Iași in 1686. These circumstances led the high Moldavian prelate to leave the metropolitan seat and to retreat to Poland together with the King Jan Sobieski, having the sole purpose of saving the treasury of the Metropolis. The scholar prince addressed, albeit tangentially, these aspects in his works Vita Constantini Cantemirii…, Descriptio Moldaviae and The History of the Ottoman Empire, in which he expressed a completely different opinion about the reasons that led the metropolitan to leave Moldova together with the Polish king and he disapproved of his father’s gesture towards the Moldavian hierarch, even if he had been pursuing the goal of returning Dosoftei to Moldova with the entire treasure and the relics of Saint John the New of Suceava. The nuances that are brought in the study can easily complement the atmosphere in which these events happened, filled with tension and dramatism.