The middle section of this book focuses primarily on the Bannister brothers, members of the minor gentry who both critiqued settler colonialism and yet simultaneously promoted and made careers from it. John William Bannister settled in Upper Canada after being demobilized from the navy at the end of the Napoleonic wars. John William’s interaction with the Six Nations helped launch the long career of the Bannisters as supposed experts in Indigenous affairs. This chapter discusses the struggle of John Brant and his cousin Robert Kerr to have the Grand River headlands returned to the Six Nations, and the efforts of John William and Saxe Bannister to support a Brant–Kerr embassy to London to that effect. The chapter also discusses the involvement of both William Johnson Kerr, a descendant of Joseph Brant, and John William Bannister in the controversial colonial career of Robert Gourlay in Upper Canada. It concludes by exploring the commission of inquiry proposed by Saxe Bannister into British relationships with the Six Nations, and the related efforts of the Bannister brothers to broker Indigenous expertise for colonial positions.