O’Brien is a total mystery. This novel raises more questions about O’Brien than it answers. An Inner Party member and a large, burly man with a thick neck and a brutal face, he wears black overalls, which we think are supposed to give him an authoritative air. He is about forty-years-old, and Winston has an intellectual crush on him. Why? O’Brien has privileges that Winston doesn’t. If he is a member of the rebellious Brotherhood, as Winston believes, then he also has balls that Winston doesn’t. (If Winston is afraid to act, then O’Brien, or at least Winston’s conception of O’Brien, is a gutsier version of our protagonist.)
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A powerful and cunning man, O’Brien tricks Winston into believing that he is a member of the anti-Party Brotherhood. He is completely duplicitous. O’Brien approaches and inducts Winston into the group, but does that in order to set Winston up for the ultimate crime. Later, O’Brien even runs the show on Winston’s torturing. Talk about betrayal. At one point, he tells Winston that the Party had captured him himself a long time ago. Was O’Brien at one point rebellious, just like Winston? Who knows. We don’t really trust anything this guy says anymore. This is still a fascinating line, however. We don’t know if O’Brien was once rebellious, and, quite frankly, it doesn’t matter. Just as Winston comments that once a person is erased from history, he ceases to have ever existed, so once a person is converted, he ceases to have ever been a rebel. The ambiguity of O’Brien’s former role is more poignant than if we knew for sure that O’Brien used to be a rebel.Lastly, O’Brien’s character really hits home with this dual, conflicting emotions business. It starts with Julia, right? Winston both hates and wants to screw her. Similarly, throughout the text, Winston both admires and hates O’Brien. He also both loves and despises the Inner Party and, actually, Big Brother in general. "What is going on", you say? We direct you to the lovely little passage in the opening chapter that says, "War is Peace; Freedom is Slavery; and Ignorance is Strength." It’s almost as if we, the reader, get the same confusing and conflicting information that Winston does. It’s almost like we experience the same emotions and terror.