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Masaomi Kida is one of the main protagonists of the light novel and anime series Durarara. He is a resident of Ikebukuro and Mikado Ryūgamine's best friend from childhood. He is the one who encourages Mikado to come to Ikebukuro. He is enthusiastic about picking-up girls, despite repeated failures and acts as the comedic foil to Mikado and Anri in the early portions of the series.
He is voiced by Mamoru Miyano in the Japanese version of the anime and Bryce Papenbrook in the English version.
Masaomi's usual attire consists of a white hoodie, jeans, and sneakers. During his time in the yellow scarves, he wore a black jacket with a white shirt along with his gang's titular accessory.
Masaomi has a very friendly, enthusiastic, and outgoing personality, and is almost always seen fooling around, smiling, making bad jokes, teasing friends, and hitting on girls. He is shown to care deeply for his friends, having to act as a sort of big brother for Mikado as he adjusts to life in the big city and going to great lengths to protect those who are close to him. When Mikado first sees Masaomi in Ikebukuro, after years of separation, Masaomi's bubbly personality and bad jokes are what convince him that the man greeting him is indeed Masaomi Kida.
As the series progresses, it is revealed that Masaomi's enthusiastic, happy-go-lucky demeanor is actually a mask of his true, much less secure self. He appears to agonize over major choices much more than any other character in the series, although he falls short of being paralyzed by his fears, still being able to make important decisions when necessary. He also demonstrates a feeling of responsibility for those close to him, taking attacks on his friends very personally. Despite appearing carefree, his experience as leader of the Yellow Scarves makes him painfully aware of the realities of life, and his greatest fear appears to be allowing himself or his friends to "cross over to the dark side," preferring that they stay completely away from the color gangs even to the point of being ignorant of them. As the leader of the yellow scarves, Masaomi has also demonstrated a ruthless demeanor when confronting his men. He showed no heistation at all when physically or verbally berating other members who went against his orders. Even members who were older than Masaomi seemed genuinely intimidated by him.
In terms of abilities, Masaomi is shown to be a proficient street fighter, being able to easily incapacitate several of Horada's henchmen before being overwhelmed by sheer numbers.
Masaomi founded the Yellow Scarves when he was in middle school, intending it to be a playful sort of team. As the Yellow Scarves grew, they became one of the notorious 'color gangs' that went around the city, occasionally fighting each other. However, as the gangs grew older, one of their rival gangs, The Blue Squares, began to get serious, stretching the boundaries of a typical gang of middle schoolers and becoming quite violent. The Yellow Scarves naively expected a fair battle, but the Blue Squares allegedly played dirty and only picked fights that they could win, devastating the Yellow Scarves.
It was during the Yellow Scarves/Blue Squares war that Masaomi met Saki Mikajima, a girl who recommended him to an informant, Izaya Orihara to help him fight his wars. Masaomi was, quite reasonably, put off by Izaya's personality and found it difficult to trust him, but Izaya's advice was sound, giving the Yellow Scarves intel on Blue Squares hangouts and teaching them how to fight. The success Izaya brought to the Yellow Scarves led Masaomi to unintentionally become dependant on him for help, and Izaya continued to provide information until the Blue Squares was cornered and about to be finished off.
Thanks to Izaya, Masaomi and Saki saw each other and talked a lot, eventually deciding that they were, in fact, dating. Unfortunately, Saki was kidnapped and tortured by the Blue Squares in an attempt to lure out Masaomi, and end the Yellow Scarves. Masaomi sought Izaya for help, but Izaya would not answer his phone, and Masaomi was left helpless and unable to save her. Fortunately, Kyohei Kadota and a group of the Blue Squares who were disgruntled by the gang's lack of honour betrayed their gang and saved Saki, although she had to be hospitalized for a year.
Masaomi left the Yellow Scarves after the war, and vowed never to go to "the dark side" again. However according to Izaya, the incident made Saki his "god," with her becoming the embodiment of his dark past that he could never escape from.
It was through chats with him that Mikado Ryuugamine decided to come to Ikebukuro, lured in by the sense of excitement and fun that his friend Masaomi described (Masaomi left out the harsher details of his life in the big city, including his gang experience, as he believed it to be better that Mikado would never find out about them). Hearing about how bored he was with his small town life, Masaomi encouraged Mikado to join him and enroll in Raira Academy.
Dollars/Mika Harima Arc
Masaomi first appears to give Mikado an official welcoming to Ikebukuro. Despite their time apart, the two of them get re-aquanted very quickly as Masaomi shows him around. He introduces Mikado to a few of the more notable residents such as Simon and Kadota's Gang while also warning him about a few of the more dangerous individuals such as Shizuo and Izaya.
The next day, he congratulates Mikado about how he and Anri were selected as Class representatives, playfully teasing him about his apparent attraction to her.
Later he and Mikado come across Anri being bullied and, just as they try to form a plan to step in, Izaya interrupts them by pushing Mikado into the fray. After things settle down with Izaya chasing the bullies off, he asks Masomi to introduce him to his friends. Masaomi then reveals that he went to Raira Academy because of Izaya. They are interrupted once again by the arrival of Shizuo Heiwajima who attacks Izaya with a trash can. As Masaomi tries to think of a plan to escape, Mikado suddenly takes Anri's hand and runs. Masaomi presumably went home after the dust settled.
The next day, Masaomi, Mikado, and Anri go to the park where he buys ice cream for the whole group. He and Mikado then listen to Anri while she talks about her missing friend, Mika. That night, he gets called over by Mikado because Mikado bumped into a girl on the street and dosen't know what to do.
Masaomi goes over to see the girl and to get a proper explanation of what was happening. Mikado explains that the girl was being chased by the Black Rider but Masaomi is more than skeptical, remarking that others wouldn't believe his story either. He drives this point home the next day as he blurts out everything Mikado had told him the night before to several classmates only to get brushed off as a liar.
Knowing that Mikado was interested in the Dollars, Masaomi takes him to the roof to see if Ryo Takiguchi is a part of the Dollars. Masaomi asks the question straight out, which Mikado yells at him for. Ryo tells them the truth, and says he is in the Dollars, explaining his view of the group in the process. At the end of school, Masaomi ends up in a big fight at the student council meeting, so he can't walk home with Anri and Mikado.
The next day he tells Mikado about the Dollars meeting that happened the other night, and that the Headless Rider really has no head. He then goes out to get lunch. Masaomi hits on Anri, causing Mikado to kick him in that face.
Masaomi sees Anri being harassed by her teacher, Takashi Nasujima. Masaomi steps in, pretending to joke about telling the teachers about Nasujima's actions. Nasujima attempts to brush Masomi off until he pulls out a camera, proving he was serious about going to the teachers if he kept harassing Anri. Masaomi later appears to, once again, stop Nasujima from harassing Anri, this time dropping the name Haruna Niekawa, to scare him off. Masaomi expains to Anri that Haruna was the previous student that Nasujima was fixated on before she was forced to transfer.
Yellow Scarves Arc
After seeing Anri in the hospital because of the Slasher, he rejoins the Yellow Scarves as their leader. He declares that the yellow scarves current objective is to hunt down the slasher as well as to search for more info on the dollars, crushing them as well if they prove to be connected to the slasher somehwo.
After musing about his past, Masaomi hears one of his guys saying that someone is spying on them. Masaomi runs to see who it is and sees the Slasher on the back of the Black Rider's motorcycle. One of his men throws a metal pipe at them and the Slasher cuts it in half and they get away. Remembering that the Black Rider was at the Dollars meeting, this cements Masaomi's belief that the dollars and the slasher are allied with each other.
The next night, Masaomi visits Saki in the hospital to talk to her about recent events with Saki mentioning how she sees him from her window all the time. The conversation brings up bad memories and Masaomi leaves, with Saki cryptically saying she knows he'll come back.
Masaomi visits Kyohei and his crew to talk about how to handle the situation with the dollars and yellow scarves. Kyohei simply tells Masaomi to follow his gut but Masaomi refuses to accept such a vague answer. As the conversation gets more heated, Simon attempts to diffuse the situation as he brings them their food but they continue anyway.
Dennis gets angry because their talk is scaring the customers away so he throws a knife in the room, and tells them to stop talking about such a violent topic. Masaomi leaves and reluctantly seeks help from Izaya with Izaya revealing that Mikado is the leader of the Dollars. Masaomi tells his men to stop the attacks on the Dollars but they refuse to listen.
That night, Horada tells Masaomi that his men were beating up each other for no reason, spurred to interfere with each other by Anri's Saika. The next day, as his men go after Anri, Masaomi grabs her and drags her into an alley to help her escape. He confronts her about being the Slasher, and Mikado being the leader of the Dollars. In the midst of his talk, he accuses her of manipulating him and Mikado, causing Anri slap him in the face and run away. He eventually gets a call from Horada saying that he knew that Mikado is the leader of the Dollars, and that he took control of the Yellow Scarves. He also tells Masaomi that he is weak and not needed before hanging up. An angered Masaomi makes the decision to run there by himself and to take care of the Yellow Scarves.
Simon sees Masaomi and notices his grim demeanor. He tries to dissuade Masaomi from doing anything reckless however, Masaomi doesn't take his advice and keeps running. Masaomi confronts Horada at the base but Horada throws a crowbar at his head, and Masaomi bleeds while picking it up. The Yellow Scarves then start attacking Masaomi upon Horada's orders but Masaomi manages to hold them off while simultaneously advancing towards Horada. One yellow scarves member throws a metal pipe and Masaomi's head, disorienting him enough for Horada to gain the upper hand.
Just when Horada is about to shoot Masaomi with his gun, a Yellow Scarves member under Anri's control stops him. Eventually, Anri, Mikado and Celty arrive at the scene, and the three friends notice each other.
Horada orders the rest of the Yellow Scarves to kill them all, but Kyohei suddenly appears and springs his trap. It is revealed that several of the yellow scarves members who showed up that night were actually dollars members that Kyohei and Saburo called in to help. Amidst the chaos, Horada lets slip that he was the one who broke Saki's legs. Masaomi, frustrated, punches Horada in the face before falling down unconscious. Mikado then holds him up and asks him to wake up. He wakes up telling Mikado that he doesn't want him to "go to the dark side" before falling into unconsciousness again.
He wakes up in the hospital, and the worried Anri and Mikado are relieved that Masaomi is alive. After having a heart to heart, Mikado and Anri leave to let Masaomi rest. Later, Saki comes in and tells him that Izaya told her to go out and let the Blue Squares kidnap her. The two of them confirm their feelings for each other and agree to run away together.
When Masaomi is better, he leaves Ikebukuro with Saki, and joins the chatroom as Bakyura, constantly giving Izaya (Kanra) death threats.