In the season 5 finale of the podcast, we finish the journey through the Legends of the Brethren Court book series by covering the 5th and final book, named Day of the Shadow. The Black Pearl docks in an eerily quiet Marseille, and Jack and his crew run into Carolina's father, who is eager to get his daughter back. In the chaos, Diego and Carolina are separated from the rest of the crew, and they end up in the Mediterranean Sea, where they come under attack by Ammand the Corsair, Pirate Lord of the Black Sea. Jack enlists the help of Capitaine Chevalle, Pirate Lord of the Mediterranean Sea, and all the pirates find themselves together when the Shadow Lord enacts his master plan. The Day of the Shadow begins, and Jack along with the rest of the pirates must do their best to stop him.

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