La historia comienza en el día presente, donde Simon acude a una de la clases de historia de Catarina Loss. Cuando Marisol responde una pregunta correctamente, Jon Cartwright patea su silla, diciéndole a Simon que es un imbécil. Luego, los de élite y los desechos comienzan a discutir sobre cuál grupo debería quedarse para aprender del otro. Jon reta a Marisol a un duelo, así que ella sugiere que los desechos y los élites compitiesen entre ellos en un juego de béisbol. Si los desechos pierden, los cazadores de sombras pueden hablar primero en la clase por una semana, y si los desechos ganan, los cazadores de sombras no hablarían por una semana.
Luego de las clases, todos se preparan para el juego, pero antes de que Simon pudiese marcharse, Catarina lo retiene y habla con él. Ella se dice a Simon que está en una posición única porque ella sabía de solo un estudiante que había abandona a los élites para irse con los desechos, James Herondale. Simon asume que James era un montón como Jace, ya que James era un Herondale como Jace, pero Catarina le dice que él era lo opuesto, y que Matthew Fairchild era más como Jace. Matthew era adorado por todos, incluyendo Catarina, excepto por James. Catarina dice que James era un hijo de un cazadores de sombras y demonios.
La historia viaja a la Academia de Cazadores de Sombras en 1899, cuando James Herondale estaba viajando hacia la Academia con su padre, Will Herondale. James estaba nervioso de ir a la Academia de Cazadores de Sombras, pero no era muy bueno interactuando con otros. Él recuerda ver a su padre hacer reír a la gente como si fuera se segunda naturaleza, pero James era "de los más normal". Will dice que él y Tessa no estaban seguros de enviar a James a la Academia, pero que ellos sintían que los habían aislado en Londres, y que necesitaban darle la oportunidad de socializar con otros jóvenes de su edad. James sabe que él prefiere estar aislado, como se evidencia cuando Lucie, su hermana menor, fue a Francia y se hizo amiga de Cordelia Carstairs, mientras que él nunca hizo amigos en ningún viaje. De hecho, el único amigo de James fuera de su familia es Grace, pero nadie sabe que se conocen. Will expresa su esperanza de que James se convierta en amigo de Alastair Carstairs, el hermano de Cordelia, y Will dice que lo extrañará cuando esté en la escuela. James reposa su cabeza en el hombre de su padre por el resto del viaje, y piensa sobre su deseo de tener un parabatai.
When James and Will arrive at the Academy, Will asks Dean Ashdown for a tour of the Academy. James is left alone in the courtyard, where he sees Christopher Lightwood, James' cousin and the son of Cecily and Gabriel Lightwood, and Thomas Lightwood, the son of Sophie and Gideon Lightwood. Christopher is described as tall with light brown hair and lavender eyes, while Thomas is shorter. Since both boys are quiet in nature, James believes this to be his only chance to make friends, so he goes over to speak to them, but Matthew Fairchild beats him to it. James is acquainted with Matthew, as Matthew's parents are Charlotte Fairchild and Henry Branwell, the heads of the London Institute before Will. Matthew is the complete opposite of James; he easily converses with adults and is the type of person who can make babies stop crying. Sadly, James realizes that Matthew is friends with Christopher and Thomas already. After James awkwardly introduces himself, Ragnor Fell, their new teacher and a warlock, comes over looking for Christopher. Christopher does not confirm his identity when he speaks to Ragnor, so Ragnor gets irritated. However, Matthew is able to charm Ragnor with The Smile, one that is guaranteed to work on all adults. Ragnor is slightly appeased, but he asks Matthew to confirm that he will ensure that all explosives are kept away from Christopher at the Academy. Matthew agrees, albeit wordily, and Ragnor storms off. Matthew and James have a conversation about Oscar Wilde, their favorite author, when Alastair Carstairs comes up to them and says that they should worry themselves with Shadowhunter concerns, not mundane ones. James describes Alastair as being fair haired but with dark eyebrows, "like very judgmental black brushstrokes", and James is shocked 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 give his assistance to the young ones, but he comments that at least Matthew can talk, while James remains silent. Alastair and his friends then proceed to mock James' 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. When he resurfaces, he realizes that everyone has left the courtyard. Eventually, James finds the dining room, where all of the returning Shadowhunters are talking to each other, and the new students are watching them. Matthew, meanwhile, tells Christopher and Thomas that he needs to be selective with who he hangs out with. James interjects, saying that Alastair was right; people come to the Academy to protect people, and that is a worthy goal, but Matthew does not view it as such. Matthew invites James to sit with him at the lunch table, but James declines and sits with a mundane named Mike Smith. When Mike learns that James is a Shadowhunter, he is shocked, but James assures him that his mother was a mundane. A mundane girl named Esme Philpott comes to the table and introduces herself, but she says that she will change her name when she becomes a Shadowhunter. James is shocked that a girl would come to the Academy, as most Shadowhunter families kept their girls at home. Mike asks James if his mother had trouble ascending, and James does not answer the question in fear that he will explain his mother's parentage—half Shadowhunter, half demon—wrong. nstead, he says that he knows many mundanes who have ascended, including Sophie Lightwood. Then, Alastair comes over and insults James for hanging out with the dregs, but James spends the rest of the night with the dregs anyway. Meanwhile, Matthew Fairchild is at the biggest table with everyone listening to his stories, including Alastair.
After dinner, James asks Dean Ashdown to show him where his room is, as he missed that portion. 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 reads for the rest of the night and consequently is late for class the next morning. During training classes, Matthew refuses to participate on the grounds that it is not art, but he eventually says that he is at the Academy against his will, and this is his way of protesting it. Although the teachers are exasperated by him, Matthew never gets expelled from the Academy. Later, Thomas asks James to hang out with him more, but James says that he does not want to spend more time with Matthew. Thomas begs James to try and get along with Matthew, because the other elites think that James is strange for hanging out with the dregs. James angrily refuses, saying that the mundanes are not bad, and Thomas should know that, considering that his own mother was a mundane. Thomas said he never thought of it that way, and 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.
Eventually, every teacher except Ragnor Fell left the Academy due to Matthew Fairchild. Ragnor allowed everyone to do whatever they wanted, except he was successfully able to intimidate Matthew into participating in class. When Ragnor asks someone to teach Matthew what he has learned, James volunteers, thinking that Matthew is likely not a good Shadowhunter. However, he is proven wrong when Matthew beats him every time. In anger, James trips Matthew with his staff, and Matthew says that everyone generally likes him. Annoyed, James says, "Well, congratulations" and stands up, only to find himself directly in the path of Christopher's battering ram. James should've died, except that he transformed into a shadow before the ram could hit him, something that James later learns was warlock magic.
James wakes up in the infirmary with Uncle Jem by his side. James realizes that it is never a good thing when the Silent Brothers come to the Academy, so he asks Jem why he is there. Uncle Jem tells him that no one was hurt. However, Jem says that James can turn into a Shadow, a being not of flesh and blood, due to his demonic heritage. Uncle Jem says that he believes that James should leave the Academy, as he will be moved to mundane quarters due to Shadowhunter parents being afraid that he will contaminate their children. However, James does not want to leave because he is afraid that his mother will believe that it is her fault that James left the Academy. Uncle Jem reassures James that he is not a coward; when he was young, Tessa was afraid that she could never have children, so he told her that the right man would care. Will cared, but Jem never told her about his feelings for her. Uncle Jem say that only Will, Tessa, James, and Lucie keep him tethered to the world, as they burn brightly enough that Jem can feel like the person he once was.
When James comes back to class, he finds that everyone is terrified of him. Mike Smith, once James' friend, runs to Clive Cartwright's table in fear and Esme flinches when she sees James in the halls. James now lives a life of solitude at the Academy, spending as little time near everyone else as possible so that his darkness will not rub off on them. Also, James does not sleep well, as he wakes up in fear that he will slip into the shadow world. One morning, James feels closed in by the ceiling in his room, so he sits outside on the Academy grounds. It is slightly raining, so he holds his palm out to catch it in his hand. When James wishes that he could disappear, his hand disappears, the rain sliding through it as if it wasn't there. Suddenly, James hears someone running, and he looks up to find that it is an unhappy-looking Matthew Fairchild. James does not know what Matthew unhappy about, and he tells him so. Matthew gets angry and retorts that James is so judgmental that one can hardly breathe in his presence. James says that he'd trade places with Matthew in an instant, and Matthew does not understand why. Matthew reveals that he is jealous of James because the Dean is trying to push him out of the school, while no matter what Matthew does, he is never expelled, because his mother is the Consul. James asks why he would want to be kicked out of school, and Matthew tells him that he has taken care of his father, Henry, all these years, because Charlotte is busy and his brother, Charles Buford, follows her around, and he did not want to leave him. Matthew says that he has tried to be the worst Shadowhunter possible, and it is still not enough to get expelled. James takes this to mean that he does not appreciate art and beauty, but Matthew does appreciate it. Matthew says that Christopher and Henry are geniuses, like Leonardo da Vinci, and the Shadowhunters look down on them for it. James suggests that Matthew be an actor, but Matthew does not want to be exiled from his family forever, and he is actually good at fighting. He wishes that Shadowhunters had more options, but James says that it is their duty to make mundanes' lives possible, and there is great beauty in that. Matthew then asks James why he does not train at the Institute, and James responds that in order to do that, his parents would have to know why he was expelled. Matthew says that he likes Aunt Tessa, and he wishes that she would visit more often. However, James knows that she never will because the Shadowhunters judge her parentage, and it would be even worse now that she had tainted James, and likely even Lucie. Matthew says he can understand why James does not want to leave the Academy, but he still does not understand why James dislikes him so much, and James says that he likes humble people, so Matthew laughs. Then, James tells Matthew the truth—he is jealous of Matthew because he is easily able to interact with people. Meanwhile, James is quiet and "an unholy abomination upon this earth." Matthew observes that James is aloof, but James protests, saying that he does not interact with people well, and he was jealous of Matthew first. Matthew is confused, checking to make sure that James meant that he doesn't like Matthew because he is so charming, and he laughs when James confirms this by staying silent. James is hurt, as he is sharing his innermost feelings with Matthew. Matthew responds that if James thinks he is charming now, then he hasn't seen anything yet. James smiles at this, and Matthew is pleased that he has finally gotten through to James.
After their encounter outside of the Academy, Matthew takes James to sit with him at breakfast. To James' delight, Christopher and Thomas are glad to see him, because Matthew's feelings were hurt when James did not like him. Christopher almost sets his sleeve on fire when he leans too close to a candle, but Matthew takes it away from him and warns James to never let Christopher near fire. James says that it must be difficult for Matthew to watch over Christopher when surrounded by his adoring public, and Matthew says that he only had those people over to make James jealous. Thomas rejoices because he won't have to attend any more parties, and he says that he is not witty like Matthew, "aloof and above it all like James or living in cloud cuckoo land like Christopher." Thomas then reveals that he came to the Academy to get away from his bossy sisters, Barbara and Eugenia, but he would still rather deal with them than the parties. James is puzzled that everyone thinks he is aloof, but Matthew reminds him that everyone thinks he is "an unholy abomination on the earth." Christopher asks why that is, and James tells him that he can turn into a shadow. Christopher then requests that James allow him and Uncle 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 go 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 if he looks like him demon grandfather, aside from his eyes. Thomas is distressed by this question, and he begs Christopher to not ask Ragnor Fell if he is green like his demon father. Christopher is confused, as he apparently didn't know that he had a green teacher. Matthew says that James looks like his father, or he will once he grows into his good looks. James is secretly pleased about this comment. 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 upon 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, which were put there by older students. James is glad that the demons will be small, but he knows that demons in a Pyxis are always dangerous, as his Aunt Ella was killed by one when she was younger than James. With no demons in sight, Matthew jokingly wonders if the older students too were distracted by the beautiful day to lay out the Pyxis boxes, but he stops mid-sentence when he sees Clive Cartwright in the heather, dead, holding an empty Pyxis box. James immediately deduces that Clive was trying to play a trick on him; he likely wanted to give James a scare, and since he probably thought that demons don't hurt their own kind, James would run away. At that moment, a Vetis demon approaches them, and James turns into a shadow and cuts off one of its heads. Then, Matthew shoots the demon in the face as James simultaneously cuts off the other head remaining, and the demon dies. Then, James, still a shadow, flies through the woods, with Matthew behind him, and discovers Alastair Carstairs 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' talents, but he is still scared, so he declares that he will call him Jamie for a while to make himself feel better. The boys fail to realize that Clive is dead, and someone will pay for it, and that someone turns out to be James; he is expelled from the Shadowhunter Academy.
James is isolated from everyone in the infirmary until his father arrives to pick him up, but he does receive visitors. Esme comes to give him a hug and she promises to contact him as soon as she ascends, and Ragnor comes to James and asks him why he never came to him for help, and that he could be a warlock if he wanted to. James replies that he wants to be a Shadowhunter and, disgusted, Ragnor leaves. Christopher and Thomas also come to visit, but Christopher brings a fruit basket under the assumption that James is sick, and Thomas apologizes profusely for this. The one person who James expected to see that did not come was Matthew. When Will arrives, James is shocked to see that he has not come to charm the Dean into letting him stay, but instead grimly escorts James out of the Academy. James asks how Tessa reacted to this, and Will responds that she was very upset, but she is happy that he is coming home. When Will and James go outside, Matthew is waiting in the courtyard, and he asks James if he has been expelled. James says yes, and just as Matthew is about to say something in return, Alastair Carstairs approaches them. Will is delighted to see him, not knowing what he did to James, but Alastair is not, and he stares at the flagstones as he apologizes and wishes James luck. James accepts his well wishes, and Matthew informs Alastair that he put all of his belongings in the south wing, and Alastairs departs speedily. When Alastair leaves, Matthew begs Will to take him to the London Institute too, since he has also been expelled from the Academy. Matthew explains that in about four minutes, the south wing of the Academy will explode, as he gave Christopher explosive materials, and Matthew left a note explaining his role in the explosion. Matthew begs Will again to take him to the Institute, as he and James cannot be parted because they are going to be parabatai, and Will agrees. 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 asks if that is excessive, but James elbows him, because Matthew will soon know why Will is obsessed with the Silent Brothers. Matthew tells James that they can train part of the year at the London Institute, and part of the year at Charlotte'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, and Matthew says that he and James do not need to be parabatai—he only needed Will to think so to get Will to take him to the London Institute—unless James wants to be his parabatai. James then thinks that he expected his parabatai to be quiet like him, but his actual parabatai is going to be Matthew, the life of the party and a kind person. James agrees to be Matthew's parabatai, and he holds on to Will and Matthew for the rest of the journey home.
The story goes back to the present day, and Simon is happy that everything worked out well for James. However, Catarina says that it is no victory, as James was chased out of the Academy, and everyone who loved James had to leave, too. Simon does not understand why Catarina told him the story, and Catarina tells him that he must strive to learn from the past and be better for it. Simon leaves, knowing that he missed the baseball game, but he is delighted to find that the dregs won the match. Simon then realizes that Catarina told Simon the story because Ragnor Fell had told it to her. Now that Simon knows, Ragnor will live on in his memory. That night, Simon is writing a letter to Clary when George comes in and asks him why he wasn't at the baseball match. Simon says he was with Catarina, and George says that he if could, he would be Simon's parabatai, but he knows that Simon already has someone 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. Since she is missing from his life, it is not the same, and he wants to get her back. The story ends with Simon thinking that he is going to ask Clary to be his parabatai.