Simon is not the first student to feel out of place at the Shadowhunter Academy—half-warlock and total bookworm James Herondale certainly didn't quite fit in with the other students. Simon learns about James' time at the Academy and discovers what it means to find a place you belong in this prelude to The Last Hours.
Shadowhunter Academy, 2008:
In the present day, Catarina Loss is teaching a History class. Marisol Garza answers a question correctly, and Jon Cartwright kicks her chair, annoyed that the "dregs" have once again done something right. Simon calls him out for this, leading to an argument between the elites and the dregs about which group could stand to learn more from the other. Jon challenges Marisol to a duel, which Beatriz Mendoza objects to, but then Marisol suggests that the dregs and elites compete against each other in a game of baseball. If the dregs lose, the Shadowhunters get to speak first in class for a week, and if the dregs win, the Shadowhunters don't talk for a week.
After class, everyone prepares for the game, but before Simon can leave, Catarina pulls him aside to talk to him. She says that Simon is in a unique position because she knew of only one other student who dropped from the elites to the dregs—James Herondale. Simon assumes that James was a lot like Jace, both being Herondales, but Catarina says that he was the opposite and that Matthew Fairchild was more like Jace—liked by everyone, including Catarina, except James. She begins to tell her about James, who was born into a situation that has fated him to a difficult life—he was a child of a Shadowhunter and a warlock.
Shadowhunter Academy, 1899:
James is on his way to the Academy with his father, Will Herondale, for his first day. He is nervous as he is shy and not very good at interacting with others. Will and James's mother, Tessa Gray, had been skeptical about sending him to the Academy, but they felt that they have isolated him in London and wanted to give him a chance to socialize with other kids his age. But James felt that it isn't his parents' fault, it was his own that he made few friends. James remembers that his only friend outside of his family is Grace, whom no one could know about and was more isolated than him. Will expresses his hope that James will become friendly with Alastair Carstairs, reminiscent of his own parabatai, Jem Carstairs whom James knew as Brother Zachariah. James thinks about his own desire to have a parabatai and became scared that if he did not make friends at the Academy, he would never find a parabatai.
Once at the Academy, Will asks Dean Ashdown for a tour of the Academy. Left alone in the courtyard, James spots his cousins, Christopher and Thomas Lightwood, and James is filled with hope that he could be friends with the two boys who also seemed quiet in nature. He goes over to speak to them but Matthew Fairchild pushes past him and beats him to it. James is familiar with Matthew—he is the son of Charlotte and Henry Fairchild, two people who are very important and close to his own parents. James notes that Matthew is the complete opposite of James, able to easily converse with others.
James realizes that the three were already friends and he may not have a chance, but still introduces himself. Ragnor Fell, a warlock and their teacher, comes over looking for Christopher. Ragnor is miffed at Christopher's vagueness, so Matthew answers for him instead. Ragnor reminds Matthew about his promise to be responsible for Christopher, who was recently involved in an explosive incident. Matthew agrees, albeit wordily, and Ragnor storms off.
Matthew and James have a conversation about Oscar Wilde when Alastair—the boy his father wants him to be friends with, also the brother of Cordelia, his own sister Lucie's best friend—overhears, comes up to them and says that they should worry themselves with Shadowhunter concerns, not mundane ones, surprising James that Alastair is not friendly like Cordelia. Matthew responds that he'd rather be in a place where culture is valued, but he is stuck at the Academy with narrow-minded people like Alastair. Alastair says that he was only trying to help them but then comments that at least Matthew can talk while James remains silent. Alastair and his friends then proceed to mock James's yellow eyes, and Alastair calls James "Goatface Herondale". James storms away from Matthew, believing that he was the one who got him into such trouble.
James goes into the Institute and reads a book, intending only to read for a while but ends up doing so for hours. James wanders and finds the dining room, where most of the students were mingling. He once again finds Matthew, Christopher, and Thomas. Matthew was telling them that they should sit around a small table as he did not want to be friends with the other students who came to the Academy willingly, which James responds to by saying that Alastair was right: people come to the Academy to train to be able to save lives and that it is a worthy goal, but Matthew calls the idea dull. Matthew invites James to sit with them, but James declines, after which Matthew decides to sit at a large table instead.
Meanwhile, James sits with a lone mundane named Mike Smith, who is surprised to have a Shadowhunter sit with him. They are joined by another mundane, Esme Philpott. During their conversation, James doesn't answer direct questions about his mother, not wanting to reveal her parentage as wrong. Alastair teases James for hanging out with the dregs, and James realizes that his new derogatory nickname "Goatface" has stuck with the older students. James stays with Mike and Esme, but he sadly notices that Mike wanted to be at Matthew's table, which had become crowded and filled with students, even Alastair, who seemed interested in what he had to say—making him feel worse, that he had become the kind of friend people settled for.
After dinner, James asks Dean Ashdown to show him to his room. Dean Ashdown takes him to his room and relays a good luck message from Will in Welsh. When James gets to his room, he is distressed to find that Matthew is his roommate. James ends up reading every night and is late for his morning classes. Meanwhile, Matthew refused to participate in any of their training courses, using his "aesthetic principles" as his primary excuse. He complains about being forced to attend the Academy and waited for the expulsion that never came, despite his teachers' exasperation.
Thomas asks James to hang out with him and Christopher more, and though James expresses interest, he declines if it means being around Matthew. Thomas tries to convince him to get to know Matthew and tells him that him spending time with the mundane makes him an easier target by the other students, who don't like people who are different. James angrily refuses, saying that the mundanes are not bad and that Thomas should know that, considering that his own mother was once a mundane. Thomas said he never thought of it that way, and James, realizing how people in Idris rarely seemed to think, angrily points out that perhaps his father didn't tell him stories like Will did. Matthew says that "maybe not everyone listens to stories like you do," and James is shocked by Matthew's kindness. However, he is immediately turned off when Matthew tells another story to his admirers, once again feeling inadequate, that Matthew has everything James wants but does not appreciate it.
During one particular training session, supervised by Ragnor Fell as the other teachers had given up on Matthew's stubbornness, Matthew was forced into gear by the warlock who threatened to strip Matthew in front of everyone. James volunteers to "teach" Matthew and is surprised to find that Matthew is a skilled fighter. In anger, James trips Matthew with his staff, and Matthew observes that most people, except James, like him. James stands up, only to find himself directly in the path of Christopher's battering ram. James should've died, except he transformed into a shadow before the ram could hit him. Though he felt that it was warlock magic, he initially assumed it had been Ragnor who saved him—he realized later on that it was his own.
James wakes up in the infirmary with his Uncle Jem by his side. Jem tells him that he has the ability to turn into a shadow due to his mother's bloodline. He is being banished to the dregs section of the class. Jem advises him to leave the Academy, concerned for his well-being among people who don't care. However, James thinks of the guilt his mother would feel and refuses to leave, though he wants to. Uncle Jem reassures him that he is not a coward and has the same courage as Tessa. Jem tells him that his life is brightened by the thoughts of Will, Tessa, James, and Lucie.
James became much more ostracized than he had been before. Even his old friends Mike and Esme became scared of him, and the elites have begun to call him "Demon's eyes", a nickname that makes James miss "Goatface". James also does not sleep well, scared that he will slip into a world of shadows, scared that he might transform again and never return.
One morning, James sits outside on the Academy grounds in the rain. He briefly wishes that he could disappear and sees his hand disappear—he had just willed himself to turn into a shadow. Suddenly, an unhappy-looking Matthew jogs into view, and James questions his sadness out loud. Matthew gets angry and retorts that James is so judgmental, but tells him that he'd like to trade places with him, so he could get expelled and be sent home so he could be with his father, something he knows is unlikely because he is the Consul's son. He expresses remorse that Shadowhunters like him and his father and Christopher cannot pursue careers fitting for their genius and desires because they were born Nephilim. When James suggests that Matthew be an actor, the boy says that he cannot bear to be away from his family and that while he doesn't like violence, he is a good fighter, though he'd rather be an artist.
James tries to convince Matthew that being a Shadowhunter is still honorable and that though they themselves might not be able to directly "add beauty to the world," they could do so by saving mundanes who could. When Matthew asks why he's remained at the Academy despite the treatment he gets, James tells him his reasons, and Matthew decides that he shouldn't envy him. When he asks James why he doesn't like him, James admits that he is jealous; Matthew jokingly laughs at James, realizing that James was jealous of his charm, and finally with an understanding of the other, James begins to warm up to Matthew's behavior.
They begin to sit together at the Academy's dining hall, about which both Christopher and Thomas are glad. Matthew reveals to James that he only accepted the people who flocked around him to make James jealous, and Thomas rejoices because, like James, large crowds and interacting with others make him nervous, and he didn't have Matthew's wit, James's aloofness, and Christopher's carefree mind to get through it, and that he'd rather face his bossy sisters, whom he tried to escape from by going to the Academy in the first place, than parties. James is surprised to hear that people think he is aloof, and when Matthew brings up his words earlier, about him being seen by everyone as "an unholy abomination on the earth," Christopher asks why that is, and James tells him that he can turn into a shadow. Christopher finds the thought interesting and requests that James allow him and Henry to perform experiments on him, and he asks if he can do one at the table, but Matthew tells him no.
James revels at how easy it was to have gone from having no friends to having three close ones. James admits that he likes Matthew the best, and he writes letters home about him all the time. James worries, though, that Matthew only seeks him out because he wants to take care of him, like Henry, Christopher, and Thomas, but James is okay with that if that is the case.
Another day, Christopher asks James why the others call him Demon Eyes, and later asks if he looks like his demon grandfather. Thomas is distressed by this question, and he begs Christopher to not ask Ragnor Fell the same question. Christopher, clueless as ever, asks who Professor Fell is and is surprised to learn that they had a green teacher. Going back to the topic, Matthew says that James looks like his father and will even more so when he grows.
Matthew's friendship encouraged others to be friendly towards him, too, including Esme, who apologizes for her behavior and Mike's idiocy. She then clarifies that she does not like James, but she actually fancies Matthew, and she asks James to put in a good word for her. Although James' life is much easier with friends, people still call him "demon eyes" and are terrified of him. James worries that a disaster will soon occur.
At their next training exercise, Matthew insists on being paired up with James. James says that the teachers are thrilled that Matthew now participates in class, except when James is not in them, in which case he still refuses to participate. The task of the exercise is for the students to find the Pyxis boxes containing small and harmless demons, hidden around the grounds by older students. James and Matthew find the corpse of an older student Clive Cartwright holding an empty Pyxis box. James immediately deduces that Clive was trying to play a trick on him, wanting to give James a scare with a larger demon. The plan evidently backfired and Clive was killed. Suddenly, a Vetis demon appears, and James transforms himself into a shadow to fight it off. Together, he and Matthew battle and defeat the demon.
James, still a shadow, flies through the woods in search of Clive's accomplices and finds Alastair and a friend hiding behind a tree. James puts his concealed blade to Alastair's throat. Alastair's friend says that they never meant for anything bad to happen, and Clive only wanted James to leave, while Alastair stays silent. James asks them who is afraid, and he tells them to never come after him again, or they will get hurt. Alastair and his friend run away, and James returns to his human form. Matthew is impressed by James's talents, but he is still shaken so he declares that he will call him Jamie for a while to make himself feel better.
Because of Clive's death, James is deemed dangerous and is expelled, despite his innocence. He is isolated in the infirmary, the doors barred. Ragnor visits him, telling him that he had waited for James to come to him for help and is disappointed to hear that James only wanted to be a Shadowhunter. Will arrives and grimly escorts James out of the Academy. No one dared insult him in front of Will, and James knew that they never would, but they would do so behind him. James is horrified that despite his efforts, his mother still found out.
Outside, Matthew greets them and, upon confirming that James had been expelled, begs Will to take him to London with him. Alastair interrupts them briefly to apologize to James and wish him luck, after which Matthew brushes him off for them and tells him that in return as a prank, he took his belongings and put it in the south wing. When Alastair leaves, Matthew explains that he is about to be expelled because he broke his promise about keeping an eye on Christopher, in fact giving him materials that could make an explosive and had it set in the south wing of the Academy. Matthew left a note explaining his role in the explosion but apparently doesn't want to have to explain things to Charlotte. Will himself thinks of Charlotte and considers refusing, but is easily convinced when Matthew tells him that he and James are going to be parabatai.
As they drive away from the Academy, Will remarks that they could be hit by flying debris so they should visit the Silent Brothers. Matthew is baffled by this, but James stops him from questioning it, knowing that Matthew will learn soon enough why Will is obsessed with the Silent Brothers. Matthew tells James that they can train part of the year at the London Institute, and another part at the Consul's house in Idris, so that people will get used to James without being allowed to insult him in the Consul's house. James agrees that this arrangement is ideal, as Matthew will get to see more of Henry. Then, the south wing of the Academy explodes.
Matthew ponders, suddenly quiet, and tells James that they don't need to be parabatai if James doesn't want to, but James, realizing that in Matthew was a friend who cares about him, agrees to be Matthew's parabatai. James holds on to Will and Matthew for the rest of the journey home.
Shadowhunter Academy, 2008:
Back in the present day, and Simon has heard the story and is glad that everything worked out well for James. However, Catarina says that it is no victory, as James was driven out of the Academy for being different, and those who loved him could do nothing but leave, too. Simon doesn't understand why Catarina told him the story, and Catarina tells him that many lessons could be taken from the message: maybe to trust his friends, or to learn from the mistakes of the past and strive to do better. Simon thanks her for her story and leaves, knowing that he missed the baseball game, but is delighted to find that the dregs won the match.
Simon then remembers what James had said about people telling stories and people listening. He realized that Catarina had first heard the story from Ragnor and passed it onto him. He thought about stories and its bearing on the people around them, of the people involved in the stories, and how it keeps legacies alive. Simon decides to write letters to Clary and Isabelle and finally learn more about his past, not wanting to lose them.
Later, when George arrives, Simon tells him about Catarina's story and asks him about the idea of having a parabatai. George says he likes the idea and would ask Simon, but he knows that Simon already has someone else in mind. As George tells Simon about Jon's attempts to play baseball, Simon realizes that Clary is the person he'd ask to be parabatai. He knows that his life without Clary feels wrong and that he wanted to become a Shadowhunter more than ever because Clary was another thing that made it worth it, and he would get his memories back in the process. The story ends with Simon thinking that he is going to ask Clary to be his parabatai.
- The title was derived from The Picture of Dorian Gray by Oscar Wilde, whom Matthew Fairchild is a fan of. It is also an allusion to James Herondale, whose ability to turn into a shadow is discovered in the story told in this installment.
- This short story is told from two characters' points of view, namely: Simon and James.
- The story is set in 2008, while the story told from the past is set in 1899.
- The plague that Catarina is giving the lecture on is the Mandikhor poison that affected London in 1903.