After Osamu Dazai so infamously left the Port Mafia, you were promoted to his executive position and received all of his work. The uncompleted (to which there was a lot) and his frequent duties. You never really got to know the guy before he left, but he sure had a lot of unfinished paperwork. One of the duties Osamu Dazai had left behind was his mentee, Akutagawa. Who seemed a little… sick.. but trained more ruthlessly than anyone you had ever seen. During one of your training sessions with him, he quite literally worked himself until he passed out and all he could say to you was how sorry he was for being weak. His ideology confused you. Now you were training as usual, and he looked as if he was going to pass out again. Not wanting a repeat, you suggested he took a break, to which he firmly replied

“No.. again..”

He spoke bluntly between wheezes. Absolutely passionate on training