in Macedonia, as Andronikos II married off his five-year-old daughter Simonis to King Stefan Milutin in 1298. In spite of the resolution of problems in Europe, Andronikos II was faced with the collapse of the Byzantine frontier in Asia Minor, despite the successful, but short, governorships of Alexios Philanthropenos and John Tarchaneiotes. The successful military victories in Asia Minor by Alexios Philanthropenos and John Tarchaneiotes against the Turks were largely dependent on a considerable military contingent of Cretan escapees, or exiles from Venetian-occupied Crete, headed by Hortatzis, whom Michael VIII had repatriated to Byzantium through a treaty agreement with the Venetians ratified in 1277. Andronikos II had resettled those Cretans in the region of Meander river, the southeastern Asia Minor frontier of Byzantium with the Turks. After the failure of the co-emperor Michael IX to stem the Turkish advance in Asia Minor in 1302 and the disastrous Battle of Bapheus, the Byzantine government hired the Catalan Company of Almogavars (adventurers from Catalonia) led by Roger de Flor to clear Byzantine Asia Minor of the enemy. In spite of some successes, the Catalans were unable to secure lasting gains. Being more ruthless and savage than the enemy they intended to subdue they quarreled with Michael IX, and eventually openly turned on their Byzantine employers after the murder of Roger de Flor in 1305; together with a party of willing Turks they devastated Thrace, Macedonia, and Thessaly on their road to Latin occupied southern Greece. There they conquered the Duchy of Athens and Thebes. The Turks continued to penetrate the Byzantine possessions, and Prusa fell in 1326. By the end of Andronikos II's reign, much of Bithynia was in the hands of the Ottoman Turks of Osman I and his son and heir Orhan. Karasids conquered Mysia-region with Paleokastron after 1296, Germiyan conquered Simav in 1328, Saruhan captured Magnesia in 1313, and Aydinids captured Smyrna in 1310. The Empire's problems were exploited by Theodore Svetoslav of Bulgaria, who defeated Michael IX and conquered much of northeastern Thrace in . The conflict ended with yet another dynastic marriage, between Michael IX's daughter Theodora and the Bulgarian emperor. The dissolute behavior of Michael IX's son Andronikos III Palaiologos led to a rift in the family, and after Michael IX's death in 1320, Andronikos II disowned his grandson, prompting a civil war that raged, with interruptions, until 1328. The conflict precipitated Bulgarian involvement, and Michael