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Overview
Reward: Possibly Diamond "Clear Eye"
The reward from the youngest brother is a treasure map to dig up a diamond, worth quite a bit once you've maxed out the Trade skill in the Mind tree.
1 - Fisherman, Fish Eye
Speak with Fish Eye to begin this quest. You'll sail to #2 to Thomas Cook's house and find out what the trouble is.
2 - Pirate's House, Thomas Cook
Cook would like you to sort out who should be the new head of the family once he passes away. To accomplish this, speak with each of his sons at #3, #4, and #5. In order to get the treasure map, you'll want to give Cook's bandana to the youngest son at #5.
3 - Pirate's Den, Harry
Speak with him about his reason to become the head of the family.
4 - Pirate's Den, John
Speak with him about his reason to become the head of the family.
5 - Pirate's Den, Brenden
Speak with him about his reason to become the head of the family. Once you've spoken to all three, giving the bandana to Brenden gets you a treasure map. Open your inventory, and choose Info to see where the diamond is buried. Mine was in the Eastern Islands, on the northern most island of the inner island circle.