When answering this question, it is vital that the reader look to both the Iliad and the Odyssey to determine whether Odysseus meets the criteria of a good leader. First, let us examine his role in ending the siege of Troy and ensuring victory for the Greeks. When all of the invading Greeks have given up hope after the almost ten year long stalemate at the gates of Troy, and after many of his fellow leaders have died (Achilles, Ajax, et all) Odysseus formulates a plan using cunning and subterfuge to penetrate the gates of Troy by hiding himself and other Greeks in the faux gift of the Trojan horse.
The plan requires stealth and creativity, and it also requires Odysseus to convince his comrades that such a ruse could possibly work, when many are skeptical. Of course, the plan does work and leads to the fall of Troy. Without a doubt, this victory proves Odysseus' leadership skills in battle. He gets his men to trust and follow him, using persuasive rhetoric and by appealing to his men's patriotism and desire to get home. These are the hallmarks of a great leader.
Yet in the Odyssey, Odysseus certainly makes some questionable decisions, and all of his countrymen eventually die on that voyage. That said, the voyage home is plagued by the wrath of Poseidon, Aphrodite and other gods who oppose the Greeks and hate Odysseus for sacking Troy. Poseidon controls the seas on which Odysseus and his men travel, and it is debatable whether another leader could have steered his men home safely. They are all so tired from the Trojan War and face such obstacles that their deaths are less an indictment of Odysseus's leadership than a demonstration of Odysseus’ remarkable skill as a survivalist, and the strength of his guardian, Athena.
To examine Odysseus' skills as a leader during his voyage home, one can look to the Island of the Lotus Eaters, where Odysseus's scouts could have been stranded forever, hooked on the narcotic that delays so many there forever. Instead, Odysseus manages to find his men and take them away from the island by force so that they do not become captives to their own sloth, forget their homes and families, and succumb to addiction. Odysseus again displays his creative leadership when he forces his men to fill their ears with wax as they travel by the Sirens, whose sweet songs have shipwrecked thousands of men on the sharp rocks nearby.
Yet the perils of the ocean and the wrath of gods set against him are too great. Odysseus manages to outsmart the Cyclops, Polythemus, who kills many of his men and enslaves Odysseus for a time. He manages to navigate his ship between the sea monsters, Scylla (the hydra-headed leviathan) and Charybdis (the whirling vortex), and even though many of his men die, others survive because of Odysseus' bravery and unwillingness to succumb to despair.
Odysseus' remaining countrymen die because they fail to heed the warnings of Tiresias and Circe, who tell them not to eat the cattle on the Island of Helios. Odysseus himself does not eat the cattle, and thus survives. Again and again, Odysseus tries to instill in his men the same stoicism and self-control that he possesses, but they are not able to do so. For that reason, it is difficult to lay the blame for their deaths on Odysseus' lack of leadership. If anything, his men might have perished much sooner without his problem solving skills and ability to find inspiration and hope when hope seems like madness.
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