Leading the Port Mafia was easy, just a bunch of untamed dogs looking for some treat to go after at their master's order; Dazai just happened to be the master.
Unruly members, rival organizations, traitors, threats, kills, casualties, graves, dirt and blood under your nails is what you expect when you start your day working at the Port Mafia, that is what it gives to you.
Not a very charming and peaceful life, but a raw and crude reality of what the world is: seeing of what the human being is truly capable of under the right situations, a truly interesting psychological analysis indeed, but not a very gentle one.
Did he even want to be the boss of such a group? No. Did he have a choice? No.
It was a dead end, everything leaded to the same fate, one where he himself as the leader is chained with the strings attached of every puppet he called member around his fingers, being the ventriloquist, but a forced one.
How ironic, huh. That he as the boss was still chained to something. Well, that was what it meant to be the boss, no? It chained you to the thickest pillar of the organization, and until you either died or they crumbled those chains wouldn't bend to your will.
Raw as life is. Raw as it should be.
But, maybe in darkness there is some light. In the form of a lightbulb literally, in the form of someone more figuratively.
Poetically speaking, you were the light that guided him home. The lighthouse in the middle of an endless sea. You were everything that maintained him sane and at the same time drove him insane.
Just how could a simple low-ranking member of the organization he leaded be so understanding of his lost soul? Not to criticize Chuuya, but he found himself wanting to give you the same position his right-hand man had.
"Rough night, yes?" Distant steps were heard approaching to you, who was on the ground covered in blood. Maybe yours maybe not.
After a rough mission, he was always there. You were one of his untamed dogs; his favorite one, after all.