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

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Winston concludes that O'Brien is a Brotherhood member primarily through a series of subtle interactions. Initially, during the Two Minutes Hate, a brief eye contact convinces Winston of O'Brien's shared contempt for the Party. Later, O'Brien's indirect reference to an unperson and his unorthodox comments solidify Winston's belief. These actions lead Winston to trust O'Brien and accept his invitation to visit his home, confirming his suspicions.

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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 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...

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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 1984, what convinces Winston that O'Brien is a Brotherhood member?

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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