A pious and honest man according to his biographers, Stefan Dragutin (pr. drah-GOO-tin) was always troubled by the shady circumstances surrounding his assumption of power from his father. Consequently, he took a broken leg in a hunting accident six years later as a divine warning and serious bad omen, which coupled with some other factors, led to the council at Dezevo and his effective abdication in favor of younger brother Milutin (1282). However, Dragutin did not disappear from the political scene, having retained appanages from both Hungarian and Serbian lands in the northwestern part of the state, which included Macva, Srem, and the strategic city of Belgrade, parts of eastern Bosnia and Sumadija, and other areas further south.

Throughout all this time - perhaps in part due to family bonds - he remained in favor of strong ties with the West in general, and the Hungarian court in particular. The relationship with his brother was more tumultuous, having gone through several ups and downs during the period of over thirty years; the two did, however, cooperate in several major campaigns, including the advance against Byzantium in Macedonia during 1283/4. Also notable are the ties Dragutin forged with his Bosnian neighbors, as his son-in-law, Stjepan Kotroman, became the founder of a more stable dynasty of Bosnian bans; this relationship eventually was to justify a certain continuity of Serbian royal institutions in Bosnia, starting with Tvrtko I.

Soon after his mother's death in 1314, Dragutin retired to a monastery as brother Teoktist, engaged in a very ascetic lifestyle, we are told, and died shortly thereafter. His legacy includes some splendid monasteries, most notably among them Arilje and St. George in Ras, where he was buried.