After a lackluster season 3, Black Sails is ... well, pick your favorite phrase: upping the ante. Turning it up to 11. Pulling out all the stops. Keelhauling pirates and slitting soldiers’ throats. (What, that’s not a phrase? Should be.) Long John Silver has come a-calling and there is blood in the streets. It’s a dazzling culmination of the people and events that will eventually segue into the plot of Treasure Island, and as good as it is - and it is very good - it’s still going to have a hard time topping the sack of Charles Town at the end of season 2.
The man who would become Captain Flint, one of the most feared pirates in Nassau, began as James McGraw, a British naval officer assigned to assist Lord Thomas Hamilton formulate a plan to civilize New Providence. Lord Hamilton believes that the pirate population could be turned to develop Nassau into a thriving community, if given half a chance - and legal pardon for their crimes. Over time, McGraw comes to share that belief, and becomes a close confidant of both Lord Hamilton and his wife, Miranda, eventually sharing both their beds. Thomas’ father uses that information to commit his son to a mental institution, where he eventually dies, and force McGraw and Miranda to flee to the new world, where they were reborn as Captain Flint and Mrs. Barlow.
Despite proving himself to be an excellent pirate, Flint never stopped hoping for a civilized Nassau. A place where he could stop being Flint and become McGraw once again, where he and Miranda could live a quiet, boring life as far from the sea as they could manage. It’s a dream that seems impossible until fate delivers the chance to talk to Peter Ashe, a former member of parliament who worked with Thomas and Flint on their plan for a civilized Nassau. Ashe is now the governor of the Carolina colony, and one of the most powerful men in the new world. Flint and Miranda travel to Charles Town to talk to Ashe, but they’re not there long before Miranda realizes that Ashe must’ve helped Thomas’ father betray them all, and that he is in part responsible for ruining their lives. Understandably, she flips out, declaring that she wants to see all of Charles Town burn, Peter along with it. Peter’s man shoots Miranda and puts Flint on trial for piracy.
Meanwhile, fellow pirate Charles Vane has nipped up to Charles Town to steal Flint’s ship, a sexy Spanish Man o’ War. And while he’d normally be totally on board with Flint dangling at the end of a rope, if people see Flint dead, they’re going to fear pirates less, and that’s bad for Vane, bad for Nassau, just bad all over. So Vane’s crew joins forces with Flint’s crew to rescue him, and this is where the greatest part of the show’s entire run begins. After watching these hypocrites and cowards of the new world rip everything Flint cared about away from him, and refute testimony from one of their - Ashe's own daughter - defending the pirates who saved her, you can’t help but cheer as the men of Nassau just plain wreck the place. Never underestimate someone that pissed off. Flint’s one-on-one showdown with Peter Ashe is a thing of savage justice, as he turns the dying man’s face towards Miranda’s corpse, put up on display in the town square as part of the trial. “Her word,” says Flint, “will be the last word for this place.”
His anger is born of loss. Not just the loss of Miranda, his companion of so long, and perhaps the last person on Earth who truly knew him. But for the loss of James McGraw, and the future he had hoped for. The loss of peace and a quiet life. He was willing to make huge, personal sacrifices to make his dream work, and it still wasn't enough, because the men around him were small and petty. His hurt is a palpable thing, swirling around him in dark waves that lay waste to everything they touch. It is magnificent to behold.
Flint and Vane cut a bloody swath through the streets of Charles Town, and when they finally make it back to their ship, Flint gives the order to train the Man o’ War’s guns on Charles Town. Billy Bones asks what the target is.
“Whatever’s left,” says Flint.
The pirates of Nassau do a lot of horrible things, no question. They are murderers and thieves, all. But in that moment, their anger is righteous and perfect. Their vengeance is divine. Whatever happens in the rest of season 4, the destruction of Charles Town will remain the best bit of Black Sails.