The Way of Shadows is a fantasy novel written by Brent Weeks and is the first novel in The Night Angel Trilogy. The story takes place in Cenaria City, the capital of Cenaria, which is located in the fictional land of Midcyru. It centers upon Azoth, a guild rat who seeks an apprenticeship with Durzo Blint, the city's most accomplished wetboy.
Azoth is an orphan who lives in the Warrens of Cenaria City. He and his two friends, Jarl and Doll Girl, are members of the Black Dragon guild. They make their living stealing money to buy food and pay their guild dues to Rat, the Guild Fist, an enforcer who beats anyone who doesn't pay. One night while Azoth is underneath a local tavern scrounging for coins he overhears a confrontation between Durzo Blint, the best wetboy in the city, and several unknown assailants. After Durzo slaughters the assassins, he catches the escaping Azoth and tells him not to tell anyone about it.
One day Jarl shows Azoth a secret stash of coins that he had been saving for four years. Jarl gives the coins to Azoth so that he can apprentice to Durzo Blint. After one of his contracts, Black Dragon ambushes Blint. He easily incapacitates Ja'laliel, the guild head, and scares everyone else away. Azoth follows Durzo to the Sa'kagé headquarters but stays outside. After he makes his report, Durzo discovers Azoth hiding outside and makes a run for it. Azoth tries to follow but is unsuccessful.
The next day Azoth wakes up to find out that Rat has raped Jarl and made him "one of his girls". Rat wants to punish Azoth for pursuing Durzo but Ja'laliel forbids it. However, Ja'laliel is terminally ill, and Azoth is afraid that Rat will soon be the guild head. Azoth plans his revenge on Rat for Jarl's rape, trying to turn the guild against him, but Rat lets him play the hero.
Elsewhere in Cenaria, eleven-year-old Logan Gyre believes that he is an accomplished swordsman. He insists on going with his father, Duke Regnus Gyre, to the garrison at Screaming Winds to help defend Cenaria. Duke Gyre refuses and leaves his son as the Lord of House Gyre.
Three months pass, during which time Azoth starts to get followers who also hate Rat. One of the followers steals a metal shiv for him and he plans to kill Rat. While waiting outside for Rat one night Azoth encounters Durzo. Azoth insists on apprenticing with him, even going so far as to threaten Durzo's life. Durzo finally makes Azoth an offer; if he kills Rat in one week without any help and brings proof, Durzo will apprentice him.
A travelling mage, Solon Tofusin, arrives at the Gyre estate. He is on a mission from the prophet Dorian to help Lord Gyre. When he finds out Duke Gyre has gone to Screaming Winds, he plans to head there immediately, but his plans are disrupted when he finds out that Logan has also been named Lord Gyre. Logan forces him to spar, and Solon humiliates him. He tells him that Logan's soldiers have been losing to him on purpose, which infuriates Logan. He tells his men to treat him as no more than an equal; he is soon going to join his father at Screaming Winds, and if they truly love him, they should be preparing him for the battles there. He apologizes to Solon, who is impressed with Logan and decides to stay with him, at least for now.
In the Warrens, Vürdmeister Neph Dada meets with Rat. His job is to ensure that Rat passes his uurdthan and becomes the Shinga of the Sa'kage. The Godking has plans for Cenaria and Rat is part of those plans. Neph shares a plan with Rat about how to destroy Azoth.
Four days pass after Durzo gives Azoth his challenge and Rat is still not dead. The guild is on edge because Rat is preparing to purge Azoth's followers. Azoth decides to go outside for a piss that night and while he is outside Rat kills one of Azoth's followers and kidnaps Doll Girl. Azoth lies awake all night and in the morning he runs into Durzo who takes him to see the consequences of his hesitation.
Solon is having dinner with the Gyres. They make small talk and not much else, until Solon offends Logan's mother. She tries to send Solon away, despite Logan's efforts, but Logan reminds her he is now Lord Gyre, and sends her away. Solon is even more impressed with Logan, and becomes less certain that Duke Gyre is the one he must serve. In his indecision, he heads out to a tavern.
Rat has beaten Doll Girl almost to death, and given her terrible scars on her face. Durzo plans to leave Azoth, but he insists that he will kill Rat within the week, and pleads with Durzo to save Doll Girl. Despite his protests that life is empty and meaningless, Durzo finally concedes.He finds Solon drinking, poisons him, and takes him to Doll Girl. He tells Solon that he can have the antidote if he heals Doll Girl, which he does.
Upstairs in a brothel, Durzo is meeting with Momma K. He tells her that Azoth has him worried; he doesn't think that Azoth has it in him to be a killer. At that very moment, however, Azoth is confronting Rat. Rat takes his shiv and tries to rape Azoth, who kills him by tying a weight to his ankle and dropping the boy deep underwater, and cuts off his ear to take to Durzo. He walks in right after Momma K tells Durzo why he needs Azoth. Durzo initially doesn't accept the ear as proof, so Azoth takes him to the river and shows him the body. Durzo offers him one more chance to get out, to apprentice in a clean trade, but Azoth refuses and goes with Durzo.
Azoth begins his training with Durzo, which carries on for several years. Eventually, Azoth is sent to Count Rimbold Drake, an old friend of Durzo, who will give him a new name and life. On his way out with his new identity, a poor noble named Kylar Stern, Durzo see Solon Tofusin standing with the mountainous Logan Gyre. Durzo has Kylar run into Logan then start a fight so Durzo can get away. After being beaten senseless by Logan in front of Count Drake's daughter Serah, his crush, Logan insists upon forgiving Kylar. Durzo sends Kylar into Logan's house and they soon become great friends. A few years later, Durzo enters Kylar into a swordsman tournament sponsored by the local Blademasters. The winner will become the king's new bodyguard. Durzo tells Kylar that the Sa'kagé wants to stretch its arm and remind everyone who is in charge. The catch is no Talented, or magical, contestants. Kylar is confronted by a sister of the Chantry who tells him that his conduit for magic is broken while his glore vyrden, his magical store, is huge. There is nothing to be done. Upon facing the opponents, almost all of them should have given him a much harder challenge, he learns that the Sa'kagé has stacked the racks so Kylar could win. Kylar then faces Logan who Kylar beats easily, while wearing a mask so Logan cannot discover his identity. As a middle finger to the Sa'kagé, Kylar renders Logan unconscious by a humiliating blow to the head, in order to bring attention to the fact the Sa'kagé had rigged the tournament.
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