From the time of his death in 323 BC, the life and exploits of Alexander of Macedon were continually reimagined and reinterpreted in various literary works throughout the ancient world. While modern historians prefer such authorities as Arrian or Plutarch, in Late Antiquity there emerged an amorphous collection of stories, anecdotes, and apocryphal letters now subsumed under the title of the Alexander Romance, which elaborate in remarkable detail upon Alexander's Eastern campaigns. This project seeks to examine a popular episode of the Alexander Romance: the prophecy of the Sun and Moon Trees in the apocryphal letters of Alexander to his tutor, Aristotle, which appear as interpolations in the Romance text. We will trace the various permutations of this episode, from its earliest known versions in Latin and Ancient Greek, to its medieval translations in Old English, Old French, and Arabic. Through a close philological reading of these texts, we will examine the thousand-year history of a single tale about Alexander, and see how this single literary thread unites so many different peoples and cultures which at first seem so far apart.