Ed's old friend Calico Jack drifts by the Revenge and invites himself to stay for a while. Jack quickly proves to be rude, rowdy, uncouth, and antagonistic to Stede, and brings out similar traits in Ed. Stede is unhappy with Jack's presence on the ship, but tries to be a gracious host. At Jack's request, the crew visits Blind Man's Cove, where Jack once saved Ed's life. Jack asks Stede if he and Ed are sleeping together and reveals that he and Ed have had their own "dalliances" in the past. Stede tells Ed that he doesn't like the person Ed becomes around Jack.
Jim returns to the Republic of Pirates and takes Geraldo hostage to try to extort information about the Siete Gallos from Spanish Jackie. To Jim's surprise, Jackie kills Geraldo herself and offers to bury the hatchet with Jim, as they are now even after Jackie left Jim for dead at the hands of the Spanish. Jackie tells Jim that Geraldo was a member of the Siete Gallos, but she has no idea where the remaining members are and believes they are probably dead. She encourages Jim to let go of their quest for vengeance.
That night, Jack, Ed, and the crew get drunk and practice hitting things with Jack's whip, leading to Jack accidentally killing Buttons' beloved seagull companion Karl. Stede kicks Jack off the ship, but is heartbroken when Ed chooses to leave with Jack. Ed and Jack sleep on the beach while Stede stays up all night watching them from his bedroom window. In the morning, Ed and Jack start to row away in Jack's dinghy as Stede informs the crew of Ed's departure. Jack reveals to Ed that he was sent to the Revenge by Izzy, who wanted him to lure Stede into an ambush and get Ed out before the English arrived. Ed, furious, abandons Jack and swims for the Revenge. The arriving English warships fire warning shots, one of which hits Jack. Stede tells the crew to prepare for battle, but Ed reaches the ship and tells them to raise a white flag. The English Navy boards the Revenge and arrests them all, but Ed and Stede are too overjoyed at their reunion to care.
This episode provides examples of:
- Allegiance Affirmation: While the whole crew are clearly enjoying themselves when Calico Jack comes on board, Jack killing Karl the seagull immediately turns them against him. When Stede kicks him off the ship and Jack angrily asks if anyone's going to stay with "the fop" over him, the entire crew ends up doing so.
- Blatant Lies: Jack tries to pass off killing Karl as an accident ("He flew into my whip!"), but no one buys it. When Ed joins him in the ship's boat, he hints it was intentional ("I thought there'd be more feathers!").
- Changed My Mind, Kid: Ed changes his mind about leaving Stede after realizing it's exactly what Izzy and Jack want, and returns to the Revenge just in time to save Stede from engaging in a suicidal battle with the English Navy.
- Does This Remind You of Anything?: Stede's speech to the crew about Ed leaving sounds exactly like a parent explaining a divorce to their kids, right down to telling them "we both still love you very much".
- Held Gaze: The episode ends with Stede and Ed gazing lovingly at each other as they are arrested by the English.
- Laser-Guided Karma: The first cannon the English fire hits Jack.
- Lured into a Trap: Calico Jack manages to manipulate Stede into steering the Revenge into Blind Man's Cove, a death trap with no escape, for the English Navy.
- Makes Us Even: Spanish Jackie to Jim. Instead of fighting to the death, Jackie figures that leaving Jim to die at the hands of the Spanish is good enough payback for Jim shooting one of her husbands.
- The Missus and the Ex: Ed's old friend Calico Jack spends some time on the Revenge, and Stede spends most of it jealous and extremely disgruntled.
- Mood Whiplash: Things turn sour real quick when Calico Jack accidentally kills Karl the seagull.
- Naked People Are Funny: Buttons spends the entire episode naked.
- New Friend Envy: The basic plot of the episode, by Stede over Calico Jack. While it's a case of old friend envy with Ed, as they have a history with each other, Stede is also clearly envious of Jack's popularity with the crew.
- Queer Establishing Moment: While the show was hardly subtle about it in previous episodes, Calico Jack revealing that he and Ed used to be Friends with Benefits is what unambiguously confirms that Ed is attracted to men.
- Second-Act Breakup: Blackbeard leaves with Calico Jack when he believes that Stede won't like him for who he really is. They both mope around for a bit, Lucius dumps Blackbeard's stuff in a box and drops it off with him, and eventually Blackbeard comes back just in time to save the Revenge from being blasted apart by the English Navy.
- Shoot the Hostage: Done by Spanish Jackie to her husband Geraldo when Jim tries to hold him hostage for information on the Siete Gallos.
