Captain Loon's Doubloon first appeared in the episode "Ahoy, Captain Smee!" Mr. Smee is left in command of the Jolly Roger after Captain Hook gave up his title of captain and abandoned ship with Sharky and Bones, leaving Smee to deal with the sinking ship. Luckily, Jake and his crew were sailing nearby and decided to help. Izzy used her pixie dust to lift the Jolly Roger from the Never Sea allowing Smee to patch the hole. With the danger over, Hook, Sharky, and Bones returned aboard the Jolly Roger. Hook orders Smee to return his title as captain, but Mr. Smee shocks Captain Hook by deciding to remain as captain for a while. During Smee's time as captain, he and the rest of the crew join Jake's to find Captain Loon's giant gold doubloons. Once at the valley where Captain Loon hid his doubloon, Mr. Smee accidentally triggers a pirate booby-trap destroying the flooring that the pirates were standing on. Leaving both Jake,his crew, Smee,Sharky and Bones holding onto the side chasm or hanging vines. Jake ask Izzy to use her Pixie Dust, but she was unable to reach while trying to keep herself from falling. Soon Captain Hook arrives, gloating at Smee and the other pirate's blunder as he attempts to fly over the chasm using his Whirly-Hook and take Captain Loon's Doubloon for himself. Smee order Hook to forget about the treasure and ask him to save them. Hook at first scoffed at Smee's order but when he witnesses him struggling yo keep himself from falling he rushes to his, Jake and the other pirate's aid. With everyone safe, Smee decided to return Hook to command. Captain Hook flies over with Captain Loon's Doubloon and gives it Jake. Jake and his crew soon realize the giant doubloon is actually made out various smaller slices allowing Jake and his mateys to share the treasure with Hook and crew member.