[1] His father was most likely one of the Kantakouzenoi that settled Serbia after the marriage of Serbian Despot Đurađ Branković (r. 1427–1456) and Irene Kantakouzene in 1414.
In addition, many talented Serbian and Bulgarian writers and artists resided in that city, among the most notable being Konstantin Mihailović (1430–fl.
Even after the capture of Smederevo, however, the last capital of independent Serbia, Novo Brdo resisted Turkish invasion and refused to capitulate.
The citizens of Novo Brdo still refused to admit to defeat and immediately organized an uprising which was cruelly and mercilessly quelled by the Ottomans.
He also ordered all able-bodied Serbian men to be decapitated, the children and boys to be enlisted in the Janissaries, and the girls and women of that city to be given to his soldiers and commanders as slaves.
Death became an ever-present thought and vision, a constant companion, a tormentor, the central theme and recurrent motif of his literary works.
Dimitrije had another traumatic experience, according to some chronicles, Sultan Mehmed the Conqueror executed several members of the Kantakouzenos family in Serbia; Janja was executed in Istanbul in September 1477 together with his two younger brothers Alexios and George, his four sons and twelve grandsons, on the orders of Sultan Mehmed II.