D.S.’s most important historical work remains problematical, as the question of its authorship has never been securely settled and D.S. has been, perhaps uncritically, presented as its true author. At the end of his Physiologia in the Codex 462 of the Metokhion of All-Holy Sepulchre, there is a chronicle dealing with the long period from the reign of Romulus to Murād III (r. 982-1003/1574-1595) and a composition on the Patriarchs of New Rome (Constantinople), reaching to the year 980/1572. This last work is further known as Khronikon and is not assigned an author in the manuscript. Recorded in the manuscript after Physiologia, however, it has been reasonably attributed to the pen of D.S.

The fact that it was used as a source by a number of authors in the Patriarchate of Istanbul in the sixteenth century is an indication of the significance of this work, which still remains unedited and unpublished in its entirety. Scholars of the nineteenth century already had realized its importance and modern research has shown, through philological and linguistic analysis, that the Khronikon was the main source of Historia Patriarchica by Manuel Malaxos (d. 1581), who seems to have copied D.S.’s text very closely (in some cases verbatim), both in its lexical choices and sentence structure.

The fragment that has been published is of the utmost importance for the early history of the Patriarchate, as it deals with its transfer from the Holy Apostles (after its conversion to a mosque by Meḥmed II (r. 848-850/1444-1446, 855-886/1451-1481) to Pammakaristos, and provides us with the earliest account of this important event. It has been speculated that Khronikon contains additional information about that early period. Moreover, the text of Damaskenos-Malaxos was also elaborated slightly, and in some cases, supplemented by Theodosios Zygomalas (16th cen.), another well-known intellectual in the Patriarchate. The importance of the last elaboration lies in the fact that it was sent to Martinus Crusius (d. 1607), who included its Greek text and his own valuable translation into Latin in his monumental Turco-Graecia. Already in the sixteenth century there were persistent rumors that Malaxos was not the original author of the Zygomalas-Crusius version but had copied another earlier work, which can be identified now as the Historia-Khronikon by D.S.

The importance of the Khronikon is further indicated by the fact that it was also used in the elaboration of George Sphrantzes’ (d. 1477) original Chronikon Minus into the immensely popular Chronicon Maius (ca. 988/1580) by the sixteenth century forger-elaborator Makarios Melissourgos-Melissenos (= Pseudo-Sphrantzes) (d. 1585). The importance of D.S.’s Khronikon does not stop there, as his text was also used by another immensely popular “historical” work of the Ottoman period, namely Historikon Biblion (also known as Khronographos as well as Synopsis Historion) by Pseudo-Dorotheus of Monemvasia (late 16th-early 17th cen.), which proved to be one of the bestsellers published in Venice (the first edition: 1040/1631).

D.S.’s work seems to have been the source of many other histories. He was clearly among the major scholars in the early history of the Patriarchate during the Ottoman period. Even though our understanding seems to have been improving with modern research, our knowledge of the history of the Patriarchate in the late fifteenth and in the sixteenth centuries is scanty at best and will certainly be enhanced when we possess the full text of D.S.’s work.

His most valuable work, the History of the Patriarchs of Constantinople, has never been published and it is to be hoped that it will find a modern editor, so that D.S.’s contribution to the intellectual life of the sixteenth-century Patriarchate of Istanbul will be properly evaluated and will undoubtedly assist in a better understanding of the Patriarchate under the Ottoman sultans. Its contents include all the individuals who were patriarchs in the city from its foundation by Constantine the Great up to the present day (i.e. 1572 A.D.). It includes the number of years that each patriarch occupied the highest patriarchal throne and the those who were expelled from the throne.

Another major work of D.S.’s was Thesaurus, which consists of thirty-six homilies he had pronounced (~1557-1558). D.S.’s Thesaurus was translated into a number of languages including Russian, Bulgarian, and Karamanid-Turkish for Turcophone Greeks. Another popular work is entitled Physiologia. Based on the ancient work of Oppian (late 2nd cen.) and Aelian (d. ca. 230) on animal lore, Physiologia appears to have passed as a treatise on zoology at the time. D.S. also produced works of a hagiographical nature on neomartyrs and on various religious matters. Furthermore, D.S. chose the literary genre of the dialogue to produce a satirical criticism of the practices and behavior of the high clergy, including the patriarch. Thirteen of his letters, his works on mathematics, meteorology, and astronomy survive in manuscript form and still remain unedited. His references to Plato, Homer, Aelian, Oppian, Aristophanes, and Herodotus indicate D.S.’s familiarity with ancient literature and its genres. Another indication of D.S.’s acquaintance with ancient Greek literature is his usage of the classical Attic dialect. D.S. also composed works in the spoken idiom, a tendency that was not generally favored at the time. His scholarship and command of ancient as well spoken Greek is impeccable and there are indications that he also knew Turkish, as he employed, in Hellenized form, Turkish words in his text.