 Laughing Jack is Tom and Ava's brother, although they do not tell anyone this, except Lief and his companions, in a secret letter from Tom.He lives in a caravan that is disguised by magic (like Lief's cloak) and was given great powers of sorcery by his master, the Shadow Lord.Laughing Jack was told to stop the companions' quest, (he acted more like the Sister of the West's guardian than Doran the Dragonlover in Isle of the Dead), but failed, first when he encountered Steven at The Funnel (in the territory of the lapis lazuli) and then when he broke an oath he made in the past.