@Cloneable
Ah, I didn't mean it in a way that he doesn't willingly fuck people's lives up. What I meant is that so far he was built as some kind of a spider, who casts around his nets and seldom goes out of his way to hunt his pray: he has his lackeys for this. To be more precise, I'd expect him to end his own physical interaction by just referring her to the broker, when he not only goes with them, but is portrayed as personally deceiving the woman.
Ah, and I'd argue about him putting that OL on drugs. To me it looked more like the girl gave her drugs on her own, and she's probably a user herself. Granted, Ushijima was interested in OL's fall, but the ruin of his clients would mean no more loans, which is not good. It's just, he didn't really care all that much.
As an aside, as everything about drugs in japanese media, where even yakuza, probably, are generally less exposed to them compared to an average uni student in the west, author probably have never even seen them in person.