Dichalkon - Demetrios III

Demetrios III Eucaerus ("of the opportune moment") seized Damascus in 97 BC during the prolonged fratricidal collapse of Seleucid authority, carving out a kingdom from the wreckage of his father Antiochus VIII's realm. His reign is remarkable for one episode above all others: in 88 BC he intervened in Judaea at the invitation of Pharisee rebels, inflicting a catastrophic defeat on the Hasmonean king Alexander Jannaeus at Shechem. Yet the Jewish troops then switched sides, leaving Demetrios without enough support to press the advantage. He withdrew, and Jannaeus survived to rule another decade.

Demetrios was eventually captured by the Parthian king Mithridates II and died in comfortable captivity — the ignominious endpoint of a reign that came genuinely close to reshaping Levantine politics.