Jack Sheppard is the protagonist of Confessions of the Fox. The real Jack Sheppard was born in 1702, placing Jack in his early twenties within the novel. Jack is a daring character who uses his expertise in carpentry to perform impossible heists and escapes. Jack is a transgender man whose adolescence is spent dealing with misgendering and abuse due to being assigned female at birth. He is apprenticed to a cruel carpenter named Kneebone who treats him as property and uses him for profit.

Jack’s character explores The Relationship Between Gender Identity, Rebellion, and Criminality. He gives himself the name Jack only after he meets Bess, who sees him as the man he really is (54). It is also Bess who urges him to take up thieving and reclaim his own labor and life from Kneebone’s clutches. By thieving, Jack takes all the spoils of his work (stolen goods) for himself instead of making tuffets that create wealth solely for Kneebone. Jack’s relationship with Bess is a focal point that brings together the text’s narratives surrounding labor, profit, rebellion, and gender identity. Jack’s character argues that a rebellion against one facet of the status quo necessitates a rebellion against the other facets.