Masaomi Kida

A resident of Ikebukuro and Mikado Ryūgamine's best friend from childhood. He was the one who encouraged Mikado to come to Ikebukuro. He is enthusiastic about picking-up girls, but he seems to fail at it. He was depressed and lonely before Mikado arrived because his girlfriend was kidnapped and injured during a gang war between the Blue Squares and Yellow Scarves, which he led at the time. After Anri is injured during the Slasher incidents and the rising presence of the Dollars, he is forced to become the leader of the Yellow Scarves once more.

He despises Orihara Izaya for manipulating him when he first formed the Yellow Scarves, but returns to him again for information about the leader of the Dollars and discovers it is Mikado. He leaves Ikebukuro with his ex-girlfriend, Saki Mikajima, during the conflict between the 3 main forces in Ikebukuro. Masaomi has commented on not letting Mikado "go to the dark side", claiming that he has already gone through it.

Personality
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 saw Masaomi in Ikebukuro, after years of separation, Masaomi's bubbly personality and bad jokes were what convinced him that the man greeting him was 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.

Background
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, Blue Square, 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 Blue Square allegedly played dirty and only picked fights that they could win, devastating the Yellow Scarves. It was during the Yellow Scarves/Blue Square 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 Square 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 Blue Square 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 Blue Square 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 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 years.

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 better that Mikado 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.

Protecting and teasing Mikado for his naiveness became a hobby for Masaomi, and helped him become a little less depressed about his life. On the first day of school, Mikado followed Anri Sonohara in volunteering to be class rep; Masaomi, and many other guys, were amazed at his apparent boldness (Anri is considered by many to be quite attractive, and the implication was that Mikado was going after her. Mikado however insists that he had other reasons). They all became friends after that, and started the trio if protagonists of the series, which Masaomi playfully describes as a love triangle.

It wasn't until much later in the series, when the Slasher incidents began, that Masaomi had another run in with the underworld. When Anri was attacked by the Slasher (it was actually one of Saika's "children" who attacked her; Anri is the original Saika and she had nothing to do with the Slasher incidents, although all of this is unknown to Masaomi), Masaomi was enraged at the attack on his friend and felt the need to use the Yellow Scarves power to hunt him down. The Yellow Scarves were quick to welcome back their old leader, although Masaomi found the gang to have changed drastically.

As rumours went around that the Slasher was part of the mysterious "Dollars " gang, Yellow Scarves started hunting down Dollars members, although this proved difficult due to their characteristic "invisibility." Tensions rose sharply when the feared Black Rider was seen helping someone with a Japanese sword escape a group of Yellow Scarves; the Black Rider was a known member of the Dollars, and this was seen as solid proof that they were in league with the Slasher. After this, the Yellow Scarves, still strong after years of laying low and gaining strength off of the resentment the city felt towards the Slasher, fully mobilized, hunting down everyone who was suspected of being with the Dollars and beating them up.

Of course it was unknown to Masaomi that the Dollars were actually 'led' by Mikado, and that Anri was now the Slasher (and fully in control of herself). He still disagreed with the unneccesary violence against innocents, but his gang was out of control, and ignored his orders to stop, continuing to assault the Dollars while the Dollars did nothing in response. Masaomi grew fed up with the clear insubordination of his gang, and began sensing their mutinous intentions; his suspicions were confirmed one day as he walked into the Yellow Scarves base to find Horada in his 'throne,' blatantly taking control of the gang. It turned out that as the Yellow Scarves started letting anyone join them (this was to allow those who opposed the Slasher to fight him/her), Blue Square had actually infiltrated the gang. The fact that Anri was using Saika's children within the Yellow Scarves to try and stop attacks against Dollars members helped create a sort of chaos within the gang where members started fighting each other; Blue Square took this as an opportunity to 'remove' those still loyal to Masaomi and place those still loyal to Blue Square within the gang. Horada put out an execution order for Masaomi to be carried out by his own gang; fortunately Celty Sturluson (the Black Rider) found out, and brought Mikado and Anri with her to save Masaomi. Masaomi proved able to hold his own in battle, taking on several Yellow Scarves at once, and was able to survive long enough for his friends to come to his aid. It also turned out that Kyohei Kadota and his group, now with the Dollars, had also infiltrated the Yellow Scarves, and joined Masaomi's side in the battle. It was after this battle that all three friends (Mikado, Masaomi, and Anri) learned of each other's parts in the whole war and came to terms with it.

Although Masaomi survived the battle, the execution order against him still held, and the Yellow Scarves were still strong, so it became impossible for him to freely show himself around the city. He had been avoiding Saki because of the guilt he felt for her injuries, but his scrape with death led him to visit her to try and repent; Saki surprisingly didn't mind his absence OR his habit of flirting with other girls, as she believed that he would always find he loved her more. She also revealed that she allowed herself to be kidnapped by Blue Square on Izaya's orders, and as usual she followed his orders unquestioningly. It turned out at some point, she actually realized that Izaya was simply playing destructive games with people for his own amusement (Masaomi becoming dependent on him, Saki being kidnapped, and him suddenly ignoring Masaomi's calls for help are an example. The Slasher/Dollars/Yellow Scarves war is another, although he had other reasons for spurring that one). Towards the end of the war, she overcame her idolization of Izaya and sold him out to Simon Brezhnev. Although surprised, Masaomi revealed that he also knew that Saki was faking her inability to walk. Eventually they both forgave each other for their actions, and Masaomi overcame the paralyzing guilt that forced him to stay away from Saki, and the two disappeared from Ikebukkuro together.

After the main story, a mysterious user named "Bakyura" became a member of Mikado's private chatroom (at this point the chat included Mikado, Anri, Celty, and Izaya, although not all the users were aware of the identities of some of the others). The way he spoke, his general demeanor, and the timing with which he joined led Mikado to suspect that this user was actually Masaomi; although Bakyura ignored Mikado's inquiring PMs, he repeated jokes Masaomi liked to make with Mikado (at Kanra/Izaya's expense). Although Masaomi and Saki's whereabouts are unknown, Mikado states confidence that Bakyura is Masaomi's way of staying in contact, and that the friends will meet again in the future.

Light Novel
Light Novel specific spoilers about this character per volume/chapter.

Volume 03 : He left Ikebukuro with Saki at the end of the third novel, but joined the chat-room using alias "Bakyura" to keep in touch with Mikado.

Volume 05 & 06 : Kida and Saki are working as field agents for Izaya, gathering information for him to use as a way to support themselves. Recently, Kida and Saki were asked to gather information on Yadogiri Jinnai. Kida is suspicious about the job due to the fact that it was given so suddenly and the fact that the area they're supposed to search in is very remote and isolated. Masaomi is also unsettled due to the fact that there aren't any real computers in the town they're heading to and he can't log into the chat room. Saki says that he's become too addicted to the internet and also wonders why Kida can't simply just visit them instead of just going on the chatroom. Masomi replies that he just can't see them because he fears that they won't accept him if he did go back.

After they return from their trip, Kida logs on to the chatroom to catch up but no one is on. He tries to check the archive history but finds it empty as well. He logs back on again the next day and asks Mairu and Kururi for an update on what he missed. The twins are confused as they remember Masaomi being on the day before. Kida is alarmed about this and asks if Taro Tanaka was on as well. The twins say yes and Kida immediately makes the assumption that his account was hacked and also has a good idea as to who is responsible.

Masaomi calls Izaya and asks him what he said to Mikado in the chatroom and why he hacked into his account. Izaya simply taunts Masomi about why he doesn't simply just call Mikado about it and about how he's simply acting like a coward. The insults hit a little too close to home and Masaomi lashes out at Izaya who promptly hangs up on him.

A few hours later, Saki asks Masaomi if he was lonely. Masaomi tries to deny it, saying that he has her. Saki sees through the lie and says that while she can be Masomi's lover, she can't be his friend in the same way Mikado and Anri can. She says that, form the way he described them, it would be impossible for his friends to abandon him and even if they did, She would be there to help him back up. Saki goes on to say that if Masaomi's friends are in danger, then the only person who can, and should, help them is Masomi himself. reinvigorated by Saki's words, Masaomi packs a few changes of clothes and heads out to Ikebukuro to help Mikado.

Masaomi isn't seen until much later after Mikado tried to apologize to Chikage. He see's Mikado break down in tears and immediately stops himself from calling out to him. He realizes that, with the way he was right now, he wouldn't want to be seen in that state by Masaomi. Masomi turns and leaves, deciding to re-introduce himself after Mikado had recovered.

Volume 08 : Masaomi learns about Mikado and Aoba going around and expelling dollars members and decides to investigate. Masomi learns that Mikado was chasing after Ruri Hijiribe's stalker and decides to intervene before he could do anything rash. He arrives too late and sees that Mikado has already been beaten severely by Adabashi Kisuke. Masaomi manages to get the jump on Adabashi long enough for Mikado to light him on fire. Masaomi is shocked at the level of cruelty that Mikado had shown and is disturbed at how Mikado can simply smile through it all. He yells at Mikado for what he was doing but Mikado simply brushes him off and walks away.

Masaomi eventually runs into Anri as well and the two of them have a rather cheerful reunion but both are worried at Mikado's recent behavior. Masaomi eventually decides to reform the yellow scarves with the sole purpose of bringing Mikado back to his senses as well as to crush the Blue Square remnants that have assimilated into the Dollars.

Volume 09 : Masaomi continues to frequent the chatroom and greets several of the new members that have joined (including Saki who joined at his invitation). He tries to get in contact with Mikado via private chat but Mikado simply replies that he'll be leaving the chatroom and logs off. Later, he enters Russia sushi with a yellow scarf around his neck and asks Kadota for advice.



Trivia

 * His favorite subject is English while his least favorite subject is History.
 * His favorite quote is "Love is a Leveler."