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When viewers first meet Captain Flint (Toby Stephens) on Black Sails, he’s all mystery. One can only guess as to what drove this man to become the stern-faced and stern-hearted pirate captain he now appears to be. No one seems to know his story or his motivations, though there are plenty of guesses. Even when Miranda Barlow (Louise Barnes) comes into the picture, assumptions are made that she’s the force that’s steering him and holding all his secrets. But that’s not completely true either. Flint’s real truths aren’t learned until season two’s flashbacks into his quite dramatic past. To most viewers’ shock, it is revealed that Flint had a romantic relationship with Miranda’s husband, Thomas Hamilton (Rupert Penry-Jones). This wasn’t just some torrid affair either; “Thomas wanted to clean up piracy in the Bahamas and make New Providence Island a British colony” (Jethro Nededog, TheWrap.com), and he needed Flint’s help as an officer in the British Royal Navy to do that. It doesn’t take long for Hamilton’s vision to influence Flint, and both share that dream of a better world that further enhances their love. But what’s most remarkable here is how this revelation changes the viewer’s perception of Flint.

Initially, Flint has an affair with Hamilton’s wife, Miranda. As Hamilton and Flint work together, one assumes Flint’s continuing his dalliance with Miranda behind Hamilton’s back. But oddly enough, once Hamilton makes his feelings for Flint clear (in front of Miranda no less), viewers bear witness to a rather complex love triad, one in which all three participants are loved and willing to boldly fight those who would condemn them. It’s their rebellious nature and willingness to pursue “pardoning the pirates in order to work with them for commerce to and from Nassau” (Jethro Nededog, TheWrap.com) that ends their romance and dooms their careers. Despite Thomas and Flint bringing out the best in each other and trying to make a difference and establish progress in England’s name, their relationship cannot be tolerated and all sides are severely punished.

Things seem hopeful when Miranda and Flint make it to Charlestown with their old friend Lord Ashe’s (Nick Boraine) daughter, Abigail (Meganne Young), who they rescued from a kidnapping scheme involving Captain Charles Vane (Zach McGowan). They’re hoping this peace offering will bend Lord Ashe to their wills, perhaps making him remember the past goals they all shared and their vision for Nassau’s future. But things don’t go well: Miranda deducts that Lord Ashe was the one who betrayed Flint and Hamilton, and that he did so for his position at Charlestown, which was orchestrated by Hamilton’s father, Lord Proprietor Alfred Hamilton (Danny Keogh). Miranda wants justice for her men, for the devastation of their lives and dreams. She wants Lord Ashe dead, and nothing less will do. Miranda is shot dead for her bold declarations, and what was left of Flint’s dreams and chance of happiness dies with her.

Flint is not the same man he was when he sailed into Charlestown; he was slightly broken, but he remained hopeful with Miranda and Nassau’s potential at his side. With her death, there are no more rules to follow, no more false hopes to cling to. He and Vane form an unlikely alliance, escaping their trials and authority, and sending Charlestown to its knees. Flint is changed forever and “destroyed as a person” (Jethro Nededog, TheWrap.com). With Flint, it was never just about gold, power, or glory; it was about becoming something more than himself, and delivering on a promise of a better Nassau. Toby Stephens puts it succinctly when he claims Flint “became himself with Thomas Hamilton. His potential was unleashed with Hamilton” (Jethro Nededog, TheWrap.com). Viewers can discern that Hamilton was the best thing to happen to Flint, providing both opportunity and self-discovery. Flint may have formed a man unjustly stripped of his naval career, robbed of his loves, and cheated by a corrupt and duplicitous system; but British authority created the pirate, and now they’ll have to deal with him.