The story of Dazai Osamu is started from Ougai Mori took in Dazai Osamu and Yumeno Kyusaku as his wards, before he even ascended as the Mafia Boss.
At some point, when the former Boss—whose only aim at that time was more death and destruction—was dying, Mori killed the Boss himself, with only Dazai as the witness. He then tells Dazai the cover story: that the Boss died of a serious illness and that his dying wish was for Mori to succeed him. Dazai was 14 years old.
At some point, when the former Boss—whose only aim at that time was more death and destruction—was dying, Mori killed the Boss himself, with only Dazai as the witness. He then tells Dazai the cover story: that the Boss died of a serious illness and that his dying wish was for Mori to succeed him. Dazai was 14 years old.
Dazai was a part of the Port Mafia prior to the story, and he was one of the five great Port Mafia Executives. He was the youngest person to become an executive in history (being considered as an executive before he was even 16), and a living legend within the mafia as well—to the extent that there is a saying going around the mafia: "The misfortune of Dazai's enemies is to have Dazai as their enemy".
The trigger for Dazai leaving the mafia was his old friend Oda Sakunosuke, a low-ranked mafia member—who was killed in the conflict between Port Mafia and Mimic, orchestrated by Ougai Mori to obtain an official license from the government expressing silent consent of Port Mafia's existence and its activities as an organization. Already distraught from the knowledge that Ougai intentionally drove Oda Sakunosuke into a suicidal attack against the enemy commander, Dazai took Oda's last words to heart—"I know it makes no difference to you, but please become a good human being. Save the weak, protect the orphaned. I suppose you don't care for either justice or evil...but striving to be a better person is a wonderful thing"—and decided to leave the mafia. He was 18 years old.
At the age of 20, he joined the Armed Detective Company under recommendation from Chief Taneda of the Ministry of Internal Affair's Special Ability Department, and—as a newbie—was entrusted by Fukuzawa Yukichi to Doppo Kunikida, along with administering his entrance exam. Shortly after, they were both assigned to work on the Serial Disappearance of Yokohama's Visitors Case, which Kunikida decided to be Dazai's entrance exam.
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In the years he was an Executive, roughly half of the mafia's overall profits could be solely attributed to him, to the extent that Ougai Mori mentioned that, "Given another four or five years, I wouldn't be surprised if Dazai killed me and took over my position." He was also a specialist at torturing people for information, claiming to Kouyou Ozaki that, "There hasn't been a single prisoner who hasn't spilled everything under my interrogation.". He even gave Akutagawa spartan training in using his Ability, and was the one who gave Akutagawa the idea of cutting space to shield himself.
It is stated by Akutagawa that, during a mission, he suddenly aborted it and supposedly, defected from The Mafia. Dazai later tracked down a man named Taneda, who was the acting commander for the Japanese ministry's Special Abilities Division, and requested to work in a place where he can help people. Taneda recommended the Armed Detective Company to Dazai, on the condition that he'll need at least two years laying low to cleanse his past. Later, it was his friend, Ango Sakaguchi who assisted him with that. It is unknown what he was doing during those two years, but it is mentioned by Dazai himself that before meeting the Armed Detective Company, he was an unemployed and unmotivated and drunk in a bar that he used to frequent.
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