The stories of Odysseus companions begin from the very opening of book nine, on the coast of Ismarus home to the Cicones. Odysseus and his men sacked the place and destroyed its men folk after taking their women and their vast spoils, Odysseus warned his men to dispatch with haste. But they were not quick minded enough, and a tremendous battle broke out between Odysseus and his men and the Cicones. Seventy two of Odysseus men were brutally killed. We can see here that this would cause much grief for Odysseus and his remaining companions, for his men had made it through the battle of Troy and where rejoicing to be returning home to Ithica, now he would have to return to grieving families awaiting their heroes return and for some, now their heros would never return. This is a classic example of the kind of grief Odysseus feels throughout the epic poem, because this is how many of his companions have presented Odysseus with grief, through death.
Whether it was falling in battle or devoured by a monstrous creature. For instance when, Odysseus and his remaining companions sailed to the island of the Cyclopes, where with twelve companions, he entered the cave of the Cyclops Polyphemus. This giant devoured, one after another, six of the companions of Odysseus, and kept Odysseus and his other men as prisoners in his cave. Witnessing their loyal companions cannibalistic murders right in front of them Odysseus and his men wept and raised their hands to Zeus in horror. This again must have made Odysseus overridden with grief for not only did he watch his men be killed but he was the one that led them to this ferocious one eyed monster. Again he has lost more of his men which means more grieving families; at home in Ithica questioning the Gods for the death of their loved ones.
However, death is not the only way that Odysseus is exposed to grief some of the monsters that Odysseus and his followers encountered would not kill his men but simply make them forget all longing for home, and the nostros that they were feeling. One of these monsters would be the Lotus-eaters, a race that eat the flowery lotus fruit. Some of his companions were so much delighted with the taste of this flower that they wanted to remain with the Lotus-eaters and think no more of Ithica.
This must have caused much anguish for Odysseus as he did not know how to help his compelled comrades. But being the intelligent and strong hero he is he used force to bring them back to the hollow ships, and they wept on the way but once on board he tied them up and continued with his voyage. The sirens also allow men to forget their home for with their beautiful voices would sing bewitching songs to drive these men to their death. Luckily with the help of Circe the sorceress who told Odysseus that if he wanted to hear the sirens song and live that he should allow his men to tie him to the mast of his ship while they covered their ears with softened bees wax and steer the boat onward while Odysseus listened.
Odysseus, in the epic poem has also encountered Companions that have questioned and mistrusted his leadership; this is that of Odysseus second in command of Odysseus ship during the voyage back to Ithica after the Trojan War his name was Eurylochus. In the Odyssey he is portrayed as an unpleasant, cowardly individual who undermines Odysseus and stirs up trouble. When Odysseus and his men arrive on the island of Aeaea home to Circe Eurylochus is chosen to lead a group of twenty-two men to explore the island. While touring the island they see Circes house and all but Eurylochus enters, he himself suspects Circes trap and when the men are turned into pigs he runs back to warn Odysseus.
Odysseus prepares himself to confront this witch and save his crew however Eurylochus refuses to guide him to Circes palace and urges Odysseus to escape and leave the men to their fate. This must have caused an uncountable amount of grief and pain for Odysseus for Eurylochus was his second in command, Odysseus therefore must have trusted this man with his life and thought rather highly of him. Then for him to tell him to abandon his loyal companions who have been there for him since Troy and save himself must have hurt Odysseus a great deal. After Odysseus returns from Circes palace having rescued his companions, Eurylochus insults Odysseus and threatens to kill him. Here we see Odysseus being befriended and almost killed by his second in command obviously causing much grief for our brave hero.
Overall I feel that the companions are the source of much grief for our fearless hero. However most of them did not wish to bring grief upon their leader. For most it was simply an unfortunate death leading to Odysseus grieving for the loss of them.