Stefan Dragutin child Urošica
Charles Martel's son, Charles Robert, came to Hungary to assert his claim to the throne in 1300. His grandfather, Charles II of Naples, listed Dragutin and Dragutin's wife among Charles Robert's principal supporters. Between the summer of 1301 and May 1304, Charles Robert spent much of his time in the powerful Ugrin Csák's domains, which were located to the north of Dragutin's realm, implying that Charles Robert's relationship with Dragutin was cordial. For unknown reasons, Dragutin's troops pillaged Csák's domains in 1307, but Csák launched a counter-attack and defeated Dragutin's army on an unknown date, sometime before 13 October 1307. Dragutin made an alliance with Charles Robert's opponent, Ladislaus Kán, who ruled Transylvania in the 1300s. Dragutin's Orthodox son married Kán's daughter, for which the papal legate, Gentile Portino da Montefiore, excommunicated Kán at the end of 1309. Historian Alexandar Krstić proposes that Dragutin wanted to secure the Hungarian throne for his elder son, Vladislav, and the Serbian throne for his younger son, Urošica. Records of the destruction that Dragutin and his troops wreaked in Valkó and Szerém Counties most probably refer to Dragutin's frequent raids against Ugrin Csák's territories in 1309 and 1310. His ally John Smaragd led Dragutin's army, but was defeated by Paul Garai, Ugrin's commander. Dragutin also seized properties of the Archbishopric of Kalocsa, which prevented the newly elected Archbishop Demetrius from visiting Rome before the end of 1312.
His conflict with Charles Robert forced him to fight on two fronts. He could continue the war against his brother after Serbian noblemen rose up against Milutin in the early 1310s. The Serbian prelates remained loyal to Milutin and helped him to hire Tatar, Jassic and Turkish mercenaries. After Milutin inflicted a decisive defeat on Dragutin in late 1311 or 1312, the prelates mediated a peace treaty between them most probably in 1312. Dragutin had to acknowledge his brother as the lawful king, but his Serbian appanage (including the silver mine at Rubnik) was fully restored to him. Dragutin sent reinforcements to help his brother's fight against the powerful Ban of Croatia, Mladen II Šubić of Bribir, in 1313. According to Krstić, Dragutin obviously made a peace treaty with Charles Robert in Sremska Mitrovica in February 1314. In 1314 or 1316, Dragutin signed his brother's charter of the grant to the Banjska Monastery as "the former king".Dragutin became a monk and adopted the name Teoctist shortly before his death. According to Archbishop Danilo II's biography, while he was dying, he stated he could not be venerated as a saint. He died on 12 March 1316. He was buried in the Đurđevi Stupovi Monastery. He is regarded as the second founder of the monastery, which had been built by his great-grandfather, Stephen Nemanja. On the list of Serbian saints, Dragutin is venerated on 12 November or 30 October (Old Style and New Style dates). He was succeeded, in his northern domains, by his son, Stefan Vladislav II.
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