The Headhunters Guild, usually shortened simply to Headhunters, was an organization of Dragonhollow's Second Era. In the wake of the Steel War and with the emergence of the Serkrs as the dominant power of both the Swamplands and Woodlands, the world was experiencing at unprecedented era of peace that had left some bored and in search of excitement. Matto decided to create a group that could unite those who fought on both sides of the war while still providing them a challenging outlet for their destructive tendencies.