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(Odysseus:) ‘But first there came the soul of my companion, Elpenor, for he had not yet been buried under earth of the wide ways, since we had left his body behind in Circe’s palace, unburied and unwept, with this other errand before us. I broke into tears at the sight of him, and my heart pitied him […].’(11.51-56)
Oops. Odysseus loses major loyalty points for not noticing that he was missing one of his crewmen. (Seriously, the buddy system? It might have come in handy.)
(Odysseus:) 'Right in her doorway she [Skylla] ate them up. They were screaming and reaching out their hands to me in this horrid encounter. That was the most pitiful scene that these eyes have looked on in my sufferings as I explored the routes over the water.' (12.256-259)
Considering that Odysseus has to watch his friends die basically one by one over the course of his voyage home, we're surprised that he holds up so well—particularly since he takes his responsibility to them so seriously.
(Odysseus, in his tale:) '"Dear friends, surely we are not unlearned in evils. This is no greater evil now than it was when the Cyclops had us cooped in his hollow cave by force and violence, but even there, by my courage and counsel and my intelligence, we escaped away. I think that all this will be remembered some day too. Then do as I say, let us all be won over."' (12.208-213)
Odysseus tries to cheer his men up by reminding them that they've persevered through worse—but, we don't know, that doesn't sound like much of a motivational speech to us: "Oh, come on, being stuck in the cave of a homicidal giant isn't that bad. We've been through worse." Are you inspired?