Nasty Jack

Nasty Jack is a villian who appears in The New Adventures of Winnie the Pooh  episode Paw and Order. He is voiced by Jim Cummings. Nasty Jack, the meanest horse thief, is the leader of a vicious group of horse thieves, ("Horses who steal things, comprendo?") who come to the old town Rickety Gulch to cause mayhem and engage in immoral activities. Part of what makes him so feared and cruel is what he does to sheriffs. Using his strength and his hatred for sheriffs, he "trounces" the sheriff, meaning that he takes them, puts them in a bag, and simply drops them. When Piglet reluctantly and unexpectedly becomes the new sheriff of the town, he becomes Jack's newest target.

While Nasty Jack and the other horse thieves reside in the saloon where they have Rabbit and Tigger held hostage, he is confronted by a strange new foe who claims to be made out of stuffing. This new enemy is the Masked Bear (Pooh) and his fateful steed, a masked donkey (Eeyore). Though pretty harmless, an ongoing fight with ice-cream as their weapons, causes Nasty Jack to think that the Masked Bear and his steed are a threat and must be dealt with. He ends up using them as bait to persuade Sheriff Piglet to meet him face to face.

During the showdown, Piglet's sheriff badge unpins itself and falls off his shirt. This means that not only is he not sheriff, but also because he is not sheriff, Nasty Jack becomes unable to trounce him. Piglet suggests that he become the new sheriff. Nasty Jack accepts the offer gladly, showing that the reason why he was mean was because he had never been sheriff. After he becomes sheriff, he drives away the rest of the horse thieves and becomes good.