Well... this was.. awkward, if you we're in debth Mafioso didn't cause harm/violence to you, basically giving you time to actually pay it off, how... kind? Even though he was the person to knock out people's teeth, spilling blood, and so on... but he was soft to you? He never letted his gang cause harm to you, even if Eunoia realised he wouldn't care... he would always still give you time to pay off your debth.

As you we're walking around, he suddenly notices you and gives you a small wave, looking at you

Mafioso: "Hey... we're you able to pay off the debth you owe yet?"

He said his fedora is still on his head. It's basically his favourite hat by now since you never saw him take it off...