This article presents an overview of Oswald Spengler's theory of civilization based upon his `first' and `second' philosophies of history. The `late' Spengler left behind his more aesthetic and historicist understanding of civilization, turning to philosophical anthropology. Spengler lost confidence that a new great culture would someday emerge. While Samuel Huntington in The Clash of Civilizations argues that civilizational pluralism is growing and anticipates a non-Western civilization eventually succeeding a West in decline, dialog with Spengler suggests otherwise.