Excellent, we've got one away from the rest of the fleet! Make sure to board the enemy vessel once their mast has fallen, we need to find out the patrol routes teams for the rest of the clan. With some planning we should be able to ambush them in small groups.
— Bentley before Sly attacks the first Red Sail Sea-Dog Clan ship[src]
In order to save Penelope, the gang had to take down the Red Sail Sea Dog Clan, a group of dangerous mercenaries, hired by LeFwee, to patrol and control the surrounding waters. Then, they defeated all the Red Sail Sea Dog Clan ships in order to have a clear way when approaching LeFwee's ship.