The serrated (saw-shaped) coins of the Carthaginians, Romans, Seleucids, and Antigonids remain an enigma in the history of coinage. A large reason for this has been the increased scholarly interest in silver and gold coins as opposed to bronze coinage. Despite several theories and empirical studies on the weight, orientation, and origin of the coins, there is still no definitive answer as to why serrated coinage becomes so widespread in the Late Hellenistic World. In the present paper, I will attempt to describe and reexamine the history of this type of coinage and to review past explanations of this monetary enigma in anticipation of an attempt at a new approach to these coins. Instead of a practical or aesthetic reason for their existence, these coins can be explained through the struggle for dynastic continuity and self-legitimation among the many pretenders for the Seleucid throne in the aftermath of Antiochus IV’s rule. After the serrated bronzes were instituted by Seleucus IV at Ake and Antioch, these serrated coins became an important tool of dynastic legitimation. In essence, using the serrated coins was paramount to claiming dynastic continuity from Seleucus IV. This was the reason why Demetrius I, Seleucus IV’s son and rightful successor, reinstituted the serrated fabric that had been largely abandoned by Antiochus IV. This tool of legitimation was taken over by the usurper Alexander I Balas and would later become a way for his descendants to link themselves to their predecessor. Accordingly, the serrated fabric disappears in the Seleucid Empire with the death of the last descendant of Alexander I, Alexander II Zabinas. This analysis can potentially change the way that we perceive the direction of monetary influence between states in the ancient world and shed new light on the dynamics in the Late Seleucid kingdom, a power that influenced the history of the Middle East for 3 centuries.