This dissertation presents a new portrait of mercenaries as they pertain to the island of Crete during the Hellenistic period (323-30 BCE). Mercenaries ought to be contextualized among the diplomatic strategies by which Greek cities sought to remain vital, and by which some Cretan cities even succeeded up until the Roman conquest in 67 BCE. Hellenistic Cretan mercenaries need not be considered as the output of circumstances idiosyncratic to Crete, such as economic crisis, a demand for a brand of warfare unique to the island, or an exceptional culture of violence, but rather as part of a Mediterranean-wide cultural phenomenon. Furthermore, the most secure way to identify Hellenistic Cretan mercenaries is through unambiguous labels in textual sources. The study primarily uses close readings of literary and epigraphic texts to analyze the terminology for defining Cretan mercenaries and to better understand contemporary Hellenistic portrayals of and attitudes towards Crete and Cretans, especially those in Polybius’ Histories. Chapter 1 observes that the Greek term Krēs, often taken to indicate Cretan mercenaries from Crete, could identify a person’s origin and/or a specialized type of fighter, depending on context; but it was not always an unambiguous indicator of both, i.e., a Cretan mercenary from Crete. Examining material, literary, and epigraphic evidence, Chapters 2 and 3 maintain that warfare on Crete reflected mainline practices in the Greek world. Although Krētes fighters were undoubtedly specialists, their context was hegemonic (i.e., royal, league, Roman) war, not the small interpolis warfare found on Crete. Chapter 4 first posits that Polybius uses Crete as a model to illustrate for his readers the symptoms of ailing political systems; it then applies this model to Polybius’ historical accounts of Crete, concluding that Polybius criticizes how foreign aid enabled and sustained violence amongst Cretan cities. Chapter 5 offers a close reading of mercenary recruitment clauses in inscribed alliances and corroborates Polybius’ observation: Cretan cities used alliances to create relationships that lasted beyond the immediate circumstances of alliance. Mercenaries were one means by which cities could offer substantive support for these relationships and, in turn, receive crucial aid in times of need