This paper examines four speeches by Aelius Aristides that contrast the image of Macedonian history negatively with Greek past and Roman present. Aristides' literary milieu of the 'Second Sophistic' is characterized by Greek self-consciousness and nostalgia in the Roman Empire. While writers like Plutarch and Arrian mythologize the figure of Alexander as a second Achilles and a philosopher-of-war as a means of offering subtle proof of 'Hellenic' primacy over the Romans, Aristides chooses to focus on the more negative aspects of the Macedonian legacy. To the Thebans I and II elaborately update the 'barbaric' image of Philip II found in Demosthenes, making him parallel not only, perhaps, to the Persian enemy of old but also to Rome's contemporary Parthian enemy. The Panathenaic Oration and To Rome, on the other hand, idealize the world of the present, where Athens reigns supreme in culture, Rome in conquest. Aristides' stance suggests that, despite the attractions of the 'Hellenic' Alexander, pride in Greece does not necessarily have to include Macedonian history. What is more important is that writers have some means of Hellenizing Rome, whether by idealizing a 'Greco-Roman' Alexander, or by seeing Rome as the ultimate polis.