A school teacher and master of the boys department of a school on the borders of Kent and Surrey. Charley Hexam becomes Headstone's pupil and Bradley becomes obsessed with Charley's sister Lizzie. Lizzie wants nothing to do with him and he becomes jealous of Eugene Wrayburn who also has eyes for Lizzie. He attempts to murder Wrayburn and believes he has been successful. Rogue Riderhood discovers the supposed murder and attempts to blackmail Headstone. In a later confrontation Riderhood and Headstone are both drowned.