The story of Odysseus has always seemed to be a tale of triumph. After the fall of Troy, he wanders for ten years across the seas, braving storms, monsters, and temptations, until at last, finally, he returns to Ithaca, defeats the suitors, and reclaims his throne. For centuries this has been remembered as the quintessential homecoming, the long journey completed, the circle closed. It is the archetype of what the Greeks called nostos, the return after struggle and exile, and it promises resolution. Yet, if we pay close attention to Homer’s poem, we see that the homecoming is never quite as secure as it appears. Notably, Odysseus does not stride straight into his home to be welcomed; he sneaks in, disguised and suspicious of everyone around him. His reunion with Penelope is not the instant or joyous affair that he hopes for, but rather, it is drawn out in hesitation and doubt. Even when peace is restored, it feels fragile, the result of Athena’s intervention rather than Odysseus’ own ability to reconcile with those who remain. Beneath the surface lies a deep and profound sense of unease. Odysseus has been away too long. The Ithaca he left is not the Ithaca to which he returns, and he himself has become something other than the man who once departed.

The later Greeks seem to have noticed this. Other traditions revised Odysseus’ story and imagined darker outcomes. In the Telegony, a now-lost epic known through summary, Odysseus does not enjoy years of peace in Ithaca but is killed by Telegonus, his own son by the sorceress Circe. Other myths imagined that he was fated to leave Ithaca once more and wander again. It was as though the Greeks themselves were skeptical that nostos could ever truly be final. Odysseus might come home, but the qualities that made him Odysseus: cunning, deception, restlessness, would prevent him from ever truly staying. He was polutropos, the man of many turns, and those turns could not simply stop once he set foot in Ithaca. The possibility always lurked that his homecoming might fail, or that the man who returned was too changed to belong. In this light, Odysseus begins to look less like a triumphant hero of epic and more like a tragic figure, haunted by the impossibility of rest, much like his allies from the War.

This tragic Odysseus has a surprising modern echo in the character of Captain Flint from the television series Black Sails. Flint, like Odysseus, is a man defined by exile. Once James McGraw, a promising officer in the Royal Navy, he is betrayed and loses the man he loves, Thomas Hamilton. In that loss he reinvents himself, takes on a new name, and becomes Captain Flint, the pirate feared across the seas. From that point on, his life is defined by wandering, by struggle, by ceaseless pursuit of a vision. Flint’s Ithaca is not a literal home, but the dream of Nassau transformed into a republic of the free. Again and again he fights, manipulates, and sacrifices to bring this dream into reality. Like Odysseus, he is brilliant, eloquent, ruthless when he must be, and possessed of the ability to spin stories that rally others to his cause. Flint is a modern Odysseus, driven forward by loss, cunning, and longing.

Yet Nassau, like Ithaca, resists. Flint imagines it as a home for the outcast, a place of freedom beyond the reach of empire, but repeatedly, it slips through his fingers. The island is divided by self-interest, torn apart by competing visions, threatened by British power and by betrayal from within. For every gain Flint makes, another loss follows. He can never fully secure the dream. Just as Odysseus returns to find Ithaca corrupted by suitors and uncertain loyalties, Flint finds Nassau already compromised. The home he longs for is as much fantasy as reality. It is this that makes him into a tragic Odysseus: the man who cannot stop striving for a return that can never truly be realized.

In classical tragedy, the downfall of the hero often comes not simply from external enemies but from the very qualities that make the hero great. Achilles cannot restrain his anger; Oedipus cannot escape the search for truth; Agamemnon cannot escape the cycle of violence he has entered. Flint belongs in this company. His brilliance, his vision, and his relentless drive make him formidable, but they also ensure that he can never let go of the dream of Nassau, even as it destroys him. He has no place of rest because he cannot allow himself one. He is consumed by his nostos, even as it becomes impossible. He becomes the tragic Odysseus because he embodies what Odysseus might have been had he never reached Ithaca at all, or had he arrived only to find it empty of meaning.

A crucial part of what makes Odysseus’ homecoming possible in Homer is Penelope. She is his anchor, the figure who holds Ithaca together during his absence and provides him with a reason to return. Though their reunion is strained, she represents the possibility of stability, the household preserved against time and corruption. Flint has no Penelope. The love of his life, Thomas Hamilton, is lost, and the loss is the spark that transforms him into Flint. Miranda, who shares in his exile, is also taken from him. Without an anchor, without a household to which he can truly return, Flint’s journey cannot complete its circle. His Ithaca is not a person or a family but an idea, and the tragedy lies in the fact that an idea cannot be embraced. The home he longs for is not flesh and blood but vision and memory, and no reality can live up to it.

This absence of Penelope marks one of the starkest contrasts between Odysseus and Flint. Where Odysseus is drawn back to Ithaca by the constancy of Penelope, Flint is driven forward by loss. The memory of Thomas Hamilton haunts him and propels him to remake the world in a way that could have accommodated their love, if only it had survived. His Nassau is not just a home, but rather, a monument to the life he was denied. It is an Ithaca that never truly existed, which makes the tragedy even sharper. He is not seeking to return to something preserved but to create something that has already slipped away. His nostos is destined to fail because the home has been lost before the journey even begins.

What makes Black Sails particularly powerful is that it leans into this tragic vision. Where Homer can rely on Athena to impose peace at the end of the Odyssey, modern storytelling resists such closure. In our world, there are no gods to intervene and make endings neat. Flint’s story reflects this modern awareness. Exile is permanent, and closure is elusive. Nassau can never become what he dreams because it exists in a world of empires and commerce that will not permit it. The age of piracy is always doomed to give way to the age of empire, and Flint’s struggle becomes not the path to homecoming but the descent into futility and retribution. He is the Odysseus whose wandering cannot end, the man who has turned too many times to ever completely stop.

This tragic Odysseus also speaks to the question of identity. Odysseus is always a man of many names, a trickster who survives by deception, by stories, by masks. Flint is the same. He is James McGraw, he is Captain Flint, he is the haunted lover and the ruthless pirate. His identities protect him and empower him, but they also consume him. If homecoming means returning to the self that one once was, neither Odysseus nor Flint can succeed. Odysseus remains the wanderer even in Ithaca, and Flint cannot reconcile James McGraw with Captain Flint. Their very essence resists finality, which is why their stories haunt us. They represent the human condition of never quite returning, of never fully recovering the self that began the journey.

When we place Flint alongside Odysseus, what emerges is a story not of epic closure but of tragic haunting. Odysseus reminds us of the hope that return is possible, that perseverance and cunning can bring us home. Flint reminds us of the darker possibility, that sometimes the homecoming fails, or that the home is no longer there, or that we ourselves are no longer capable of belonging. Both stories matter because both reflect human experience. We long for homecomings, yet we fear their impossibility.

The tragic Odysseus is a reminder that nostos is not guaranteed. Sometimes the wandering never ends, or the homecoming proves hollow, or the home itself has vanished. Captain Flint embodies this reality, showing us that the most painful fate may not be defeat in battle but the realization that there is no Ithaca to which one can return. His story is epic in scope but tragic in ending, and it reflects a modern understanding that closure is often impossible.

Perhaps this is why both Odysseus and Flint remain so compelling. They capture the tension between hope and futility, between the desire to return and the impossibility of truly doing so. Odysseus haunts us because he holds out the promise of reunion; Flint haunts us because he shows us the futility of chasing what has been lost. Together they remind us that the theme of homecoming will always move us, not only because we long for it, but also because we fear that we may never find it ourselves.