The second season of Our Flag Means Death begins with a vivid dream. Stede, a maestro of swordplay, duels Izzy on a beach, emerging victorious after piercing him with a knife. As Ed appears, the two men rush towards each other with eager reunions in mind. However, Stede's moment of triumph is marred by an unexpected fart, only to reveal that it was Wee John's, as the crew slumbers in a cramped cell.
As Stede pens a letter to Ed, we learn of the tight corner he and his crew have found themselves in, post their renouncement of wealth. Oluwande, with a fondness for the Swede, secured them jobs at Spanish Jackie's establishment and agreed to let them stay in the cell and work in her bar.
One day, as they toil, Richard Banes approaches Stede, but the latter artfully dismisses any knowledge of 'Stede'. In his letter to Ed, Stede portrays a rosier picture of himself and his crew's spirit, yet the truth is starkly different. He seals the letter in a bottle and casts it into the ocean, hoping it will find its way to Ed.
Stede's thoughts drift to Ed, whose first glimpse reveals a tattoo that reads "Trust no one." Ed and his crew, including Izzy, Fang, Frenchie, Jim, and a new recruit named Archie, raid a ship where a wedding is being held. Their attire, adorned with black paint and resembling Blackbeard's, conceals the faces of those who pillage the ship, leaving no survivors and claiming all valuables.
Ed ascends to the wedding take and snatches a figurine that eerily resembles Stede. We learn this is a recurrent act, committed by the crew on consecutive days. As they feast on cake, Jim wonders if they've crossed a line this time. Fang, distraught, weeps while recounting how Ed killed Ivan, lamenting that Blackbeard was not like this before.
Stede catches sight of a poster featuring Ed, prompting Oluwande to remark on his busyness. While awaiting soup at a humble shack, they discuss their dire financial situation, but Stede is adamant about waiting until they have enough for a decent ship. Sue, the shack's owner, and another woman join the conversation. Stede clarifies that he and Ed didn't break up; they're merely "on a break."
At Spanish Jackie's bar, she discovers the crew's savings jar and confiscates all the money as payment for room and board. Stede attempts to confront her, but with her 20 husbands backing her, he's left helpless. Once again, they find themselves jobless and homeless.
Meanwhile, on Ed's ship, his reckless behavior takes a toll on Izzy. Snorting rhino horn, Ed orders Izzy to discard the treasure they've stolen to make room for new plunder. Izzy, haggard and near the brink of a breakdown, relays the news to the crew, who are outraged by Ed's actions. Even more disturbing is the revelation that Ed has cut off two more of Izzy's toes. Fang offers a comforting hug to the distraught Izzy.
Stede gazed pensively at the poster of Ed, confessing that their endeavors had veered off the intended path. Just then, Richard Banes, the mysterious man, appeared again, claiming to be privy to Stede's true identity. He recounted how the Gentleman Pirate had saved his life, introducing himself as a prince of minor rank who aspired to emulate Stede's legacy. Further, he divulged that Spanish Jackie possessed a Roman puzzle chest, a treasure trove of immense worth.
Stede and his crew approached the Swede, who readily agreed to aid in the theft, citing a debt of gratitude. He advised them to strike that night, when he was fulfilling his "marital duties."
Back on Ed's ship, Izzy confronted him, voicing the crew's discontent with parting with the ill-gotten gains. He warned Ed of the toxic atmosphere and suggested an open discussion, inadvertently echoing Stede's mantra of "talking it through as a crew." This triggered Ed's ire, and he stormed onto the deck, confronting the crew with a gun. When Izzy dared to speak up again, Ed fired, striking him.
As the Swede indulged Jackie in a massage, Roach and Black Pete slyly snuck the chest from her chamber. Richard Bane lingered, insisting on leaving a calling card — a small aperitif. Stede, making the wiser choice, retreated. The commotion roused Jackie, who swiftly sliced off Richard's nose.
Outside, Stede reunited with his compatriots, discovering that the chest was filled with indigo powder. Before they could make their escape, Jackie caught them. Amidst the chaos, Sue, the soup kiosk owner, emerged as their savior. She offered Jackie a sum sufficient to secure the indigo and the crew's freedom, thus pacifying her and saving the group. With Sue now their employer, Stede and the others obediently followed her lead.
On The Revenge, Fang was distraught over Ed's shooting of Izzy. Jim sought to cheer him with the tale of the wooden puppet longing to become a real boy. They even emulated Stede's voice, and Fang managed a fleeting smile. Frenchie, now promoted to First Mate, inquired about Ed's plans. Ed described a bird born in the air, destined to sail and pillage forever, never touching land. As Frenchie departed, Ed gazed at the figurine he had stolen.
Meanwhile, in a small rowboat, Stede gazed up at the same moon that Ed beheld, offering him a silent goodnight. Olu pondered over Sue's true identity, and her companion introduced her as Zheng Yi Sao, the pirate queen.
