How does Winston conclude that O’Brien is a Brotherhood member?

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During the Two Minutes Hate ritual, Winston Smith catches O'Brien 's eye for a fraction of a second, and Winston feels certain that O'Brien harbors the same feelings of disgust towards the Party. Simply by making eye contact, Winston experiences a feeling that O'Brien is his secret ally, who views...

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Big Brother with contempt and wishes for the Party's downfall. O'Brien's glance is enough for Winston to have confidence in him and believe that he is a valuable ally.

In Book Two, chapter 6, O'Brien stops Winston at work and compliments him on his use of Newspeak in his articles. O'Brien proceeds to tell Winston that his opinion of his writing was shared by an expert whose name he cannot seem to remember. Winston immediately recognizes that O'Brien has indirectly referenced an unperson by alluding to Syme, who was vaporized. O'Brien's unorthodox comment assures Winston that he is a secret ally and a member of the Brotherhood. Winston accepts his invitation to visit his home to read the tenth edition of the Newspeak dictionary. After taking down O'Brien's address, Winston realizes for certain that O'Brien is his ally. Orwell writes, "But at any rate, one thing was certain. The conspiracy that he [Winston] had dreamed of did exist, and he had reached the outer edges of it" (201).

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In the novel 1984 by George Orwell, Winston suspects that O'Brien is a member of The Brotherhood when he starts commenting on party issues in a very leading way. However, Winston has had suspicions before and detected a strange sort of independent spirit hidden within him and wonders whether deep down he actually opposes the party. The comments made by O'Brien simply serve to confirm his worst suspicions and they appear true to form. Winston finds this very disturbing and a bit scary but gets up enough bravery to approach O'Brien, saying he is an opposer of the totlitarian state. O'Brien tells him that as a member of The Brotherhood he wants to see the end of the party when actually it turns out he is a member of the Thought Police.

Scarily, it is almost impossible to do or say the right thing in this situation because there is so much double speak and many bluffs and double bluffs. The idea is to gain the confidence of 'traitors.' catch them and try to re-brainwash them to 'better ways of thinking.'

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In 1984, what finally convinces Winston that O'Brien is a member of the Brotherhood?

Winston is finally convinced that O'Brien is a member of the Brotherhood in Part Two, Chapter Eight.  In this chapter, Winston and Julia are invited to O'Brien's apartment. Initially, Winston feels nervous that his invitation to the apartment might be a ruse, but once he arrives, O'Brien turns off the telescreen (as a means of providing some privacy), and this convinces Winston that he is indeed genuine.

Moreover, Winston is further convinced in the conversation that follows. O'Brien tells Winston and Julia that the servant is "one of us." This phrase implies that they are all of the same philosophy, that they are united by their desire to overcome Big Brother.

As their conversation continues, Winston is persuaded by O'Brien to join the Brotherhood, even though O'Brien warns him that it is a dangerous pursuit that may cost him his life.

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In 1984, what finally convinces Winston that O'Brien is a member of the Brotherhood?

In George Orwell's novel, "1984" Winston, the protagonist, has long suspected O'Brien of being a member of the brotherhood.  He is afraid to approach O'Brien, but there are certain non-verbal clues that Winston feels he has gotten from O'Brien. Specifically, eye contact in the halls at work.  One day O'Brien stops Winston in the hall at work and speaks to him about an article Winston has written and the new 10th edition dictionary.  O'Brien gives Winston a piece of paper right in front of the telescreen on which he has written his home address. He tells Winston to to stop by sometime and he will show Winston an advanced copy of the Dictionary.  Winston, at this point, is convinced that O'Brien is a member of the brotherhood and this is his way to meet with Winston outside of work without arousing suspicion.  Winston memorizes the address and throws the paper in the "memory hole.

"Winston knows it is only a matter of time before he visits O’Brien. Frightened, he feels a chilling sensation passing through his body as he has the sensation of stepping into a grave."

When he does go to O'Brien's home, he meets there with Julia.  O'Brien turns off the telescreen and now Winston is positive of O'Brien's involvement and thrilled to think that he will finally be able to act against Big Brother.

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