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"Cubby the Brave!" is the second segment of fiftieth episode of Jake and the Never Land Pirates

Plot

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 Boots of Bravery, in hopes of helping Cubby conquer his fear.
Cubby wearing Captain Hook's Boots

Cubby, marching in Captain Hook's Boots.