Hephaestion
Hephaistion Amyntoros (Hephaestion, or Hephaistion, son of Amyntor)
Curtius calls him “omnium amicorum carissimus” to the king: dearest of all the friends. Alexander himself named him “Philalexandros”–friend of Alexander–in contrast to his great rival, Craterus (Krateros), who was merely “Philobasileus”–friend of the king. By the time of his death in Ecbatana in 324 BCE (only eight months before Alexander’s own) he was the second man in the empire (Chiliarch), married to the sister of Alexander’s own wife.
He and Alexander were coevals, and had shared their education under Aristotle at Mieza. They may have known one another before that. He was not a great military leader, and Alexander seems to have kept him away from important commands in actual battle. But this does not make him the incompetent or sycophant which he has sometimes been painted. Curtius stresses that he had great freedom to speak his mind to the king. And snatches of evidence in the extant sources suggest his real gifts were diplomatic and logistical, not military. It would be wrong to dismiss him as unimportant, and unnecessary to assume him a mere yes-man in order to get along with the king. His skills and those of Alexander were complimentary, not competitive.
We know little about his looks or personality. He was tall and, apparently, handsome. He also seems to have had a reputation for both charm and quarrelsomeness by turns. Later speculation whispered that he and the king had been lovers. While this is nowhere stated plainly, it is entirely possible. Nonetheless, it would be reductive to characterise their relationship solely in this way. Our model of friendship is not consonant with theirs. Within these ancient societies where homoerotic desire was freely, sometimes emphatically, expressed, intense friendships might well develop a sexual expression even while that expression was not the focus of the friendship.
Perhaps in the end, Alexander’s own name for Hephaistion is best: Philalexandros. And so he has been known down through history: dearest of all the friends of the great Alexander.
Article by Jeanne Reames-Zimmerman , The Pennsylvania State University.
World Of Alexander The Great 
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