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After the rout of Darius, while the Persian baggage train was being catalogued, someone carried a small coffer to Alexander. The men handling the captured treasure had judged it the single most valuable object in the entire haul, which in that haul meant something considerable. He asked those around him what belonged inside a container like that. Various answers came back and he accepted none of them, announcing that he would keep the Iliad in it. He was twenty-four or thereabouts, he had just broken the largest empire on earth, and he had determined that the most precious box in Asia existed to hold a poem.
Alexander

Pietro Testa Italian ca. 1650
The copy had been corrected by Aristotle in his own hand. Alexander studied under him at Mieza in his early teens and said afterwards that his father had given him life while Aristotle had given him the knowledge to live well, the sort of remark a young man makes before a relationship curdles, and theirs curdled thoroughly. He called the Iliad an ephodion of the military art, a Greek word for travelling provisions, the supplies a man packs for a road he expects to be long. Onesicritus records that the corrected text stayed with his dagger beneath his proskephalaion, the two objects he wanted within arm's reach in the dark. Deeper into Asia, when the campaign outran its reading material, he wrote to Harpalus in Babylon requesting more, and Harpalus shipped out the histories of Philistus, a substantial quantity of Euripides, Sophocles and Aeschylus, and the dithyrambs of Telestes and Philoxenus. A man conquering the known world was filing requisitions for tragedy. Plutarch adds, on the authority of the Alexandrians themselves, that the site of Alexandria was settled after Homer's verses came to him in a dream, though he hedges that story carefully and so will I.
Six years before the casket, in the spring of 334, he crossed the Dardanelles and went directly to Troy. At the burial mound believed to hold Achilles he anointed the gravestone with oil, stripped, ran a race past it with his companions in the traditional manner, and laid garlands on it, while Hephaestion placed a second wreath at the tomb of Patroclus nearby, a piece of choreography that every ancient writer who mentions it understood perfectly. Aelian read it as a public statement about what the two men were to each other. Then Alexander said the thing I find more revealing than anything else in his biography. Achilles was fortunate, he remarked, in having a faithful friend while he lived and a great herald of his fame after he died. Offered a chance to inspect the lyre of Paris during the same visit, he waved it away and asked whether anybody had the lyre of Achilles, the instrument used to sing the glories of brave men. Paris won the woman. Achilles got the poem.
Everything after that reads as an attempt to satisfy both halves of the sentence spoken at that grave. He kept the friend, and when Hephaestion died at Ecbatana in the autumn of 324 he lay across the body for the better part of a day, refused food for two, cut his hair over the corpse precisely as Achilles had done for Patroclus, and had the attending physician executed. Eight months later he was dead himself at thirty-two. Achilles in the poem receives an explicit choice between a long obscure life and a short glorious one, and Alexander, who knew the text by heart, accepted identical terms without ever giving any sign that he recognised them as terms at all.
The pillow itself, however, is a problem. A complete Iliad copied onto papyrus runs past fifty metres of roll, and divided into eight scrolls each one comes out at roughly the diameter of a beer can, so nobody has ever slept on that, with or without a casket around it. Ancient pillows were generously sized and ancient art never shows anyone using more than two at a time. Classicists have offered a solution I prefer to the legend. Chares of Mytilene, royal chamberlain in Alexander's own court, recorded that the Persians used the word proskephalaion, pillow, as the name for the treasure chamber adjoining the king's bedroom, a vault holding five thousand talents of gold coin. The book in its casket sat in the strongroom beside where he slept, filed with the bullion at identical security, which tells you considerably more about how he valued the thing than the bedtime image ever did.
Onesicritus is the sole authority for the sleeping arrangement, and he ranks among the least trustworthy men who ever wrote about this campaign. Arrian accuses him of claiming command of the fleet when he had served as its pilot. For Aulus Gellius he belongs alongside the authors of pure fable. Plutarch cites him for the story of an Amazon queen arriving in camp for a conjugal visit, an account that reportedly made Lysimachus laugh aloud years later on hearing it read back to him. So the most famous image we hold of Alexander's private hours reaches us from a demonstrable fabulist and describes an arrangement that could not physically have existed. He had grasped at twenty-two that a life and the record of a life are separate acquisitions, and that the second is by far the scarcer of the two, so he brought a historian with him. Callisthenes of Olynthus, Aristotle's great-nephew, recommended by Aristotle himself, travelled with the army and produced Deeds of Alexander, an account describing the king in openly Homeric terms and promoting his claim to divine parentage. In 327 Callisthenes objected publicly to proskynesis, the Persian prostration Alexander wanted from Macedonians. Within months he was implicated in a conspiracy among the royal pages that he almost certainly had nothing to do with, and he died in custody, either of illness or by hanging depending on which officer's memoir you read, since Ptolemy and Aristobulus left incompatible accounts and Arrian openly doubted both. The book is lost.
So the herald was hired, the herald did the work, and the herald was destroyed by the man who wanted him. What comes down to us is a young king in a tent east of Babylon, one hand near a dagger and the other near a poem, arranging a life to match a story he had memorised as a boy. The arrangement succeeded completely. He remains the most famous soldier who ever lived, and almost nothing anyone knows about him can be checked.
Until Sunday.