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ah well, if you are on that route, if I remember correctly is to pay the million of the debt, then give him beer, talk (should come out the dialogue of the decision), if not, give him beer, then whiskey and talk to him until it comes out, you should treat him like garbage. 

you can only do this on friday at the entrance.

yeah well i completed the confrontation (josef finding out about starmaker) even before paying a single dollar for the debt...

oh...