Stede decides to fence the hostage English officer at the Republic of Pirates, a pirate haven in Nassau. Oluwande convinces Jim to let Lucius out of the trunk. Stede and Lucius take the captive officer into town to try to sell him, while Oluwande worries that Jim is in danger because Spanish Jackie, a powerful bar owner in the Republic, has put a price on Jim's head for killing her favorite husband, Alfeo.
The four of them all end up at Spanish Jackie's bar, where Jackie seemingly doesn't recognize the disguised Jim. Stede is approached at the bar by Izzy Hands, who tells him that his boss wants to meet him; Stede, not realizing Izzy's boss is Blackbeard, refuses. Jim sneaks into the back room to retrieve their family's knife from Alfeo's mummified body, but is unable to find it. Two pirates get into a bidding war over the English officer, and a fight breaks out that leads to Stede shattering the jar of noses Jackie has cut off misbehaving patrons over the years. Jackie threatens to cut off Stede's nose, and Jim recognizes her knife as their family dagger. Jackie lets Stede go unharmed after Geraldo, one of her other husbands, informs her that Blackbeard was asking after Stede.
As Stede leaves the bar, he is approached by Geraldo, who tells him that he has a client who would be interested in buying the hostage. Lucius gives Jim their family knife, which he pickpocketed off of Jackie as he left the bar. Geraldo leads Stede, Lucius, Jim, and Roach to his "client," which turns out to be the Spanish Navy. The Spanish captain stabs Stede and arrests the pirates. Geraldo peels off Jim's fake nose and beard, revealing their true identity and stating that Jackie knew who Jim was the entire time. The Spanish plan to execute Stede by hanging, but as they attempt to do so, they are attacked by Blackbeard and his crew, who rescue Stede and the rest of his pirates. Blackbeard addresses the badly wounded Stede by his nickname, "the Gentleman Pirate," and says that he's heard all about him.
This episode provides examples of:
- Agonizing Stomach Wound: Downplayed, as Stede survives, but his stab to the gut is portrayed as a very serious and painful injury.
- Batman Gambit: Jackie correctly predicted that putting an insultingly low bounty on Jim's head would bait them into coming back to her bar, allowing her to sell them out to the Spanish.
- Hanging Around: Stede is sentenced to hang from the deck of the ship, and in the commotion of battle, it takes a little while before someone manages to cut him down.
- If It's You, It's Okay: Lucius, a gay man, has a moment like this after Jim (a nonbinary person whom Lucius still thinks is a woman at the moment) gives him a big kiss of gratitude for bringing back their family's knife.
- Lured into a Trap: Geraldo tells Stede the Spanish Navy is interested in buying the captive English officer. It turns out they're actually interested in killing pirates like Stede.
- Mood Whiplash: After three episodes of watching Stede be goofily inept but largely harmless, seeing him get stabbed in the gut is a sobering reminder that Stede's incompetence puts him in genuine danger.
- Skewed Priorities: Jim is much more concerned with the insultingly low bounty Spanish Jackie put on their head than they are with the prospect of being killed.
