The episode’s framing device focuses on a play being performed by Winnie the Pooh and friends, which is titled "The Legend of Sheriff Piglet." The horse gang works for their boss Nasty Jack, who features as the main villain in the play.
After realizing that Piglet is now the sheriff of the town (as Piglet now possesses the Sheriff badge), Jack makes plans to "trounce" Piglet and sends his horse gang after the group. The group is able to escape into the Sheriff’s office.
Later, when Jack challenges Piglet to a showdown, Piglet is able to gather the courage to face Jack; however, in a twist of fate, his badge falls off. As Piglet is no longer Sheriff, Jack can no longer trounce him. At Piglet’s suggestion, Jack decides to become good, and becomes Sheriff himself, stating that he always wanted to be Sheriff. At the sight of this, the rest of the horse gang flees town after their once-villainous leader promises to clean up the town and haven’t made another appearance since.