Trouble arrives in the form of an old friend of Ed's, Calico Jack, whose partying ways take Ed back to the old days and cause tension between him and Stede.
Meanwhile, Oluwande is missing Jim but his crewmates are quick to take advantage of the room space - Frenchie and Wee John as the 'room people' is very sweet and funny. Jim themself is on a journey of revenge that eventually leads them back to Spanish Jackie's door.
Will Arnett's Calico Jack is a disruptive presence and a love-to-hate sort of character. His drunken actions with a whip cause a rift between Stede and Ed that threatens to be permanent until Ed figures out the real reason he's there.
The final scenes feature an absolutely iconic musical backing, ending with a touching reconciliation that will have you grinning like an idiot. This episode really is a stand out among a fantastic series, some of the best shot television out there.