Cubby is rather timid and is not very confident in himself. He is great with maps. He looks up to the other two as older siblings who are always there for him. He has a tendency to get upset easily but that never gets in the way of him helping to come up with a solution.
In the episode "The Emerald Coconut", it was revealed that Captain Hook does not believe Cubby to be a threat to his plans. Despite this, Cubby proved himself worthy by taking on Captain Hook with only Skully as help putting aside his great fear of him. He is also one of the crew members aboard Jake's pirate ship, Bucky.
Cubby is a short, plump young boy with blue eyes, fair skin, rosy cheeks, honey blonde hair and dirty blonde eyebrows. His outfit consists of a blue bandanna, red shorts with a large orange patch on his right legging, a white T-shirt with a V-neckline, a navy vest with gold buttons on the trims, white socks with blue trims above each of them, and brown boots with gold buckles.
Cubby is a member of a band of pirates organized by Peter Pan and consisting of himself, Jake, Izzy, and their parrot Skully. He is also the youngest of the group. He plays a key part in the overall story as the keeper of the map of Never Land. The pirate's secret hideout on Pirate Island also holds a large map room where Cubby keeps a trove of maps. Though very adventurous, Cubby is easily scared and somewhat clumsy. He appears to have low self-esteem, constantly thinking low of himself, but can be resourceful when necessary.
A few episodes revolve around Cubby such as the already mentioned "The Emerald Coconut". In "Cubby's Sunken Treasure", Cubby accidentally uncovers the lost treasure map of the legendary Captain Fisher. In "Never Night Star", Cubby is forced to face his fear of the dark when the crew goes on a journey to find the lost City of Gold.
In the episode "Cubby's Mixed Up Map", Captain Hook switches Cubby's map with a fake one to keep Jake and his crew from finding their way to the Golden Dinghy. Cubby proves his resourcefulness and keen memory recalling all the locations leading to the Golden Dinghy.
In the episode "Cubby the Brave!" when Jake and crew find a pair of abandoned boots on their hunt for the Treasure of Spikey Pike Peak, Jake suggests that they might be the legendary Boots of Bravery, in hopes of helping Cubby conquer his fear.
In the episode "Sand Pirate Cubby!", Cubby auditioned to become one of Captain Flynn's sand pirates for the day by enduring various trials of the Never Land Desert along with Bones. Captain Hook became furious that a member of his crew would ever join forces with Flynn.
In the episode "Cubby's Tall Tale", Cubby and the rest of the crew were enjoying Captain Flynn tale of adventure on Shipwreck Beach. Once it became Cubby's turn to tell a tale. In order to impress Flynn and his mateys, Cubby exaggerates his tall tale about his journey to buried treasure at the top of Hidden Peak. Unknown to the young pirates, Captain Hook overhears and sets off to find it taking Cubby's map. Jake and his crew, accompanied by Flynn, follow Captain Hook and his crew in order to reclaim both Cubby's map and the treasure.
Cubby appears as a puppet in the Disney Junior-based show at Disney's California Adventure and Disney's Hollywood Studios. Cubby joins Jake, Izzy, and Skully to retrieve their stolen treasure chest that Captain Hook plans to take.
- He wields the map of Never Land because he is the genius map reader of the group.
- Cubby is the second main character to have a solo song (in "The Golden Twilight Treasure!") with the first being Izzy (in "Surfin' Turf").
- He is not to be confused with the Lost Boy of the same name and nearly-identical appearance.
- He appears to have some talent in cooking, as revealed in the episodes "Cookin' with Hook", and "Captain Hook's New Hobby".
- In the episode "Sand Pirate Cubby!", both Cubby and Bones became honorary Sand Pirates.
- In the episode "Beardini's Apprentice", Cubby became an honorary Pirate Magician.
- Cubby has been a temporary member of the Jolly Roger twice in the series (the first time was in the episode "Pirate Swap!" and the second in "Aye, Aye Cap'n-Cap'n").