Kritobulos of Imbros is known to us as the author of one of the most important sources of the Halosis. However, his historical work covering the period from 1451 to 1467 can be regarded not only as an important source of information, but due to its author’s literary talent, as a momentous work of late Byzantine historiography. It has been long acknowledged that Kritobulos was influenced to a great extent by classical authors, in particular Thucydides. Nevertheless, relatively little research has been carried out concerning the manner in which these classical notions reappear in the Historiai. Revealing some new parallels, the present paper explores the commonplace themes present in the proem and the letter of dedication, as well as the most significant features of Kritobulos’ literary imitatio.