If we think of 2nd century Greek literature as largely “nostalgic” for the Greek past, the Battle of Chaeronea of 338 BCE, at which Philip and Alexander won a decisive victory over a panhellenic alliance led by Athens and Thebes, seems an obvious inflection point. Our writers would have been exposed to such a perspective from a young age, as the historical strife between Demosthenes, Aeschines, and Philip, and the words of the Athenian orators themselves, provided the main scaffold for Greek rhetorical education. Yet no extant 2nd century writer describes the battle extensively, and it is treated variably even by writers whom we would describe as Hellenocentric. A study of these variations is a useful tool by which we can understand better the nature and limits of Greek nostalgia and Hellenocentrism as concepts. What is revealed is a distinction between nostalgia, a longing of a return to the pre-Macedonian past, and idealism, which focuses on the continuation of Greek cultural supremacy in the Roman present. The only author who shows a strand of true nostalgia is Pausanias, who alludes to Chaeronea as the Greeks’ great disaster on four separate occasions. By contrast, Plutarch, a native Chaeronean, is more interested in his city’s prosperity under Rome; while his minimal treatment of the Battle of 338 contains echoes of nostalgic rhetoric, it is also importantly conditioned by his admiration of Alexander. Arrian, Polyaenus, and Aeneas Tacticus go even further in their positivity toward Macedonian power, variously treating Philip, Alexander, and the Macedonian soldiery at Chaeronea as quasi-Hellenic militarists. The conclusion considers what the use of Chaeronea (or lack thereof) can tell us about our authors’ stances towards Roman power, to which the Macedonians could be seen as a precursor.