Jack Sheppard

In the novel, Jack Sheppard is a trans man who previously was an apprentice to a carpenter turned to theft and prison break artist.^[8] His work with a carpenter gave him the skills to be able to break out of jail four separate times, making him the most wanted criminal in London. His illegal work as a thief parallels with forbidden queerness in 18th century London. He has a relationship with prostitute, Edgeworth Bess, who finally enables him to identify himself as a man instead of his biological sex. During the novel, she was the one who performed top surgery on him, allowing his physical body to match his identity. Eventually, another infamous London criminal, Jonathon Wild, turned Sheppard in and he was eventually executed in 1724 at the age of 22.^[9]

Rosenberg's fictional Jack Sheppard is based on the historical folk hero who lived in London in the 18th century, but it is important to note that this is not a true account. According to Rosenberg, it is unclear if the real Sheppard 'thought of himself, as trans or not trans',^[10] but he notes that in many works Sheppard is represented in a way that 'we might see now as genderqueer or gender nonconforming', and it was his small and flexible frame that helped him escape confinement so many times.^[11]

Edgeworth Bess

Elizabeth Khan, also known as Edgeworth Bess, was Jack's main love interest in the novel. Bess was a prostitute in London who had a severe disregard for authority and the law. She has an interesting background in that she identified as "lascar" who was brought to London as part of England's East India Company. In the book, she is described to be of Southeast Asian descent. She was a free spirit, made clear through her willingness to accept Jack in a society that would not.

The historical figure of Bess was actually named Bess Lyon, and Rosenberg's account of her is fictional.

Jonathan Wild

As Jack emerged into the world of thievery, he learned about the famous Jonathan Wild. Jonathan ran a business of thievery in London, though he disguised himself as a constable. After hearing about Jack Sheppard, he tried to recruit him to join his gang. Bess urged Jack to work to be a "freelance roguer" instead of joining into Wild's organized heists that revolved around bribery. When Sheppard refused Wild's offer, he was furious. Wild eventually was a major player in Jack's final arrest and his eventual sentencing to death.

Dr. Voth

Dr. Voth is the fictional character who discovered and is editing the manuscript. His footnotes give the reader a better understanding of who he is and why he is so fascinated by this manuscript. He is a professor at a university but is put on unpaid leave, giving him unlimited time to focus on this manuscript. It is clear he has many qualms with the university that he works at, and also discusses his personal life, specifically his struggles of dating as a queer man. Dr. Voth and the author, Jordy Rosenberg, have many parallels so it is important to consider that the author may have based this character off of himself. Dr. Voth's character adds a playful and comedic spin to the novel, which contrasts with the more grim aspects of the manuscript.

Identity

As a queer man himself, it makes sense that Rosenberg crafted the novel around the important theme of identity. The character of Jack is a trans man, and it is unclear if he has female genitalia or is a hermaphrodite. The lack of focus on his genitalia insinuates the fact that his biological sex is not relevant, as he eventually defines himself as a man. Furthermore, Rosenberg claims in an interview that this combined with the numerous terms to discuss genitalia all were to somewhat mock the cis-het conventions around the rigid relationship between desire and certain body parts.^[12] Rosenberg says that he was intending for the experience of genital resignification to help structure his novel.^[13] It must also be noted that Jack's gender identity would be considered differently in modern terminology to that of the 18th century, so whilst readers can recognise that his character is transgender, a large part of his identity relies on the ambiguity of his gender identity at the time.

In the beginning of the book, the carpenter he apprentices calls him “girl”, but when Bess refers to him as a “handsome boy”, he is relieved to realize that he can identify himself however he wishes.^[14] Bess is a major player in him being able to come into his own skin, and is the first woman he feels confident enough to have an intimate relationship with. Though being transgender was not acceptable in 18th century London, Bess accepted Jack which allowed him to accept himself as well. Despite an entire police force after him and the looming prospect of the death penalty, Jack's greatest fear was that his biological identity will be discovered and he will be forced to revert to living like how he did before he represented himself as a man.

This theme also relates to Dr. Voth, the editor of the manuscript, because he is a trans man as well. In the footnotes, he discusses the struggles of dating in the 21st century while transgender.^[15] Not only this, but Dr. Voth's identity as an academic makes his narration of Jack's story more credible; he is a trustworthy narrator and validates Jack's experience of trans identity through the mode of academia.

Criticism of Academia

One of the reasons Dr. Voth is so infatuated with the manuscript is because he reveals he has been put on unpaid leave by the Dean of Surveillance for "improperly utilized leisure"—playing phone Scrabble during office hours. There are many references throughout the book at his disappointment in the way he is treated as a professor at a university, and appreciates the opportunity to be able to immerse himself in the manuscript, which is something he was extremely interested in.^[16] However, he later is angered when a company called P-Quad Publishers and Pharmaceuticals coerces the manuscript from him. The university claims Voth is legally obligated to turn the manuscript over, which furthers his resentment to the institution and capitalism in general.^[17]

It is interesting to consider the possibility that as an academic himself, was Rosenberg touching on his own frustrations with his experiences working at a university?^[18] In an interview, he discusses the holistic life of study.^[19] He explains that from his time working in academia, he has come to the belief that university's goal is to make its staff feel so insignificant, they will stop struggling for a space there.^[20] This is reminiscent of Dr. Voth's experience with the publishing company as they try to take the manuscript from him, and the university tells him he is obligated to do so. Rosenberg says that a lot of times, "there are things about the university that grinds people down so badly that they should certainly not feel compelled to continue to struggle there".^[21]

Liberation

Liberation is a theme that can be discovered in almost all aspects of the novel. Even in Dr. Voth's defiance of the university's wishes for him to surrender the manuscript, he is seen to free himself from the expectations the university has for him.

It is no mistake that Jack breaking social norms with his queerness parallels with his breaking of the law and defiance of London's new prison system. In the beginning of the novel, he is an apprentice to an abusive carpenter who literally chains him to his bed at night. At this time, Jack was still forced to identify with his biological sex, which was torturous for him. Ironically, using his expertise on locks from working with the apprentice was what allows him to break out of the chains at night. This was when he met Bess and identifies himself as a man, so he is not only physically liberated from the chains but also freeing himself from the constraints of society. Furthermore, Bess is a major reason why he is able to become liberated from the fear of his queerness being discovered; she instils confidence that he would not have been able to derive from himself.