O'Brien acts as both "good cop" and "bad cop" during Winston's torture. In what manner does O'Brien still manage to portray himself as someone who is, and wants to, help Winston?
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O'Brien can be torturing Winston at one point and have Winston crying in his arms the next. Does O'Brien really care about Winston. I think he cares as far as he has an affinity for Winston's intellect. O'Brien is fascinated by Winston's keen intellect: it is the reason he gives Winston his freedom for so long. Winston becomes very much a pet project of O'Brien. O'Brien wants to see if he can change Winston. I think that is as far as he cares about him.