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During the Peloponnesian War bandits had claimed the cave as their own. During one night when the bandits were roaming the mountain range, they happened to run into Theoros and Akamas, two boys finishing up their agoge. A scuffle ensued and Akamas was slain, while Theoros was captured and taken to the Cave of Sorrows.
Soon afterwards, the misthios Kassandra found the cave as well, looking for the boys at the request of Iatrokles, the boys' agoge master. Kassandra slew the bandits, claimed their valuables and freed Theoros.