Character Analysis
It's a miserable existence.
Gregory the Jailer is the big hulking man who stays in the dungeons and oversees all the prisoners. He doesn't even have light and has to find his way around the maze of the dungeons by a rope that's tied to his ankle. All that time in the dungeons has turned him into a wild creature; when he eats, he even swallows chicken bones whole.
Despite the fact that he's spent a great deal of time alone in the darkness, Gregory decides to save Despereaux because he takes pity on the little mouse—and because Despereaux agrees to tell him a story to bring some light to his bleak existence. Somehow, spending his life in the dark dungeon hasn't made him an evil person.
We never sense much hope for Gregory, and in fact, he's collateral damage in Roscuro's scheme to imprison the princess. Roscuro needs him out of the way—Gregory would never let them take the princess—so he chews up the guide rope and Gregory loses his way and dies in the dungeon. He's a tragic character.