He was the colonel of "Bearskin's Free Company", the Fables who held back the Adversary's forces and tried to hold their last unconquered territory. It is said that he fought in many famous battles. He was known for his cunning battle strategies which were the reason that the territory held as long as it did. He also cared for the safety of the people who had loved ones and sent them on the boat to Fabletown. Boy Blue was his orderly, and he gave Boy Blue the witching cloak so Blue would live to tell the tale of the battle and so he could escape to be with Red Riding Hood. He was the one of the last of the Fables that stayed to fight to be killed; he was stabbed in the side and died slowly while the Adversary's troops mocked him.

Bearskin is based on a German "Good Soldier" fable, in which a soldier returning from war makes a deal with the devil to live as a vagabond for seven years—if he dies within the seven years, the devil takes his soul. If he lives, the soldier will receive love, happiness, and great wealth. During his wandering, the soldier becomes known as Bearskin because of his long hair and general filthy appearance. While wandering, Bearskin is betrothed to the youngest of three daughters. He breaks a ring in half: giving half to the girl and keeping half as a token of his devotion. After the seven years have ended, Bearskin returns to his fiancee. Her two elder sisters dress in their finest clothes to impress the handsome soldier (much like Cinderella's stepsisters). He presents his half-ring as proof that the handsome man is the same as the ugly wanderer. Bearskin is reunited with his love, the wicked sisters commit suicide, and the devil appears once more to gloat: "Now I've got two souls in place of your one!"