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The Figurehead is one of the three items needed to fix the machine in Ventureland that opens the door with the Projector Screen leading to Tortooga.
After the pirates broke the machine to stop Hook's new crew from following them to Ventureland, Damien Salt grabbed the Figurehead because it looks like the girl he's fallen in love with, Henrietta.
Damien will happily trade Mickey Mouse the Figurehead if the mouse sets him up with his secret crush. Mickey can either give Damien Salt flowers or Ice Cream to give to Henrietta. If the item is flowers, Henrietta falls in love with Damien and the pirate gives the figurehead to Mickey for free. If the item is ice cream, Henrietta will reject Damien. With his hopes of a relationship in tatters, Damien is willing to sell the painful reminder for 50 E-Tickets.
After Mickey gives the Figurehead to Smee, it will be attached to a rope, being yanked up and down on the contraption for the rest of the game.