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I can almost map it out

In hindsight, I can see that it was the behavior of an inveterate manipulator.*

If he's already in for so much — I can almost map out the thinking — he's probably going to figure I won't say no.

Already well in debt, he's thinking of his bargaining advantage, which is the fact that I don't want to piss him off and lose what I might get in repayment.

*Or at least habitual.