The chapter collects what may be known of Alexander’s life up until the battle of Chaeronea, for which the source of primary importance is Plutarch’s biography. It attempts to sift what may plausibly regarded as historical from embellishments of various kinds (contemporary and subsequent, propagandist, folkloric or mythologyzing). Particular attention is given to: Alexander’s three birth myths; his education at the hands of Lysimachus of Acarnania, Leonidas of Epirus and Aristotle; Aeschines’ vignette of him as nine-year-old boy; the intriguing traditions bearing upon his horse Bucephalas; his regency during the Byzantine campaign, his foundation of Alexandropolis and his dealings with the Persian ambassadors; his role in the battle at Chaeronea.