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. He also seized properties of the Archbishopric of Kalocsa, which prevented the newly elected Archbishop Demetrius from visiting Rome before the end of 1312.