Winston was very wise... but also very stupid when it comes down to other characters in the book.
First, Syme. Winston knew he was very smart, he knew that he would be taken away by the thought police. The he will vanish. And he was right, Syme disappeared on page 154. In fact, Winston says that "Syme has ceased to exist: he had never existed." Perhaps the will be meeting again... perhaps not, but he is no longer in the book at the moment. Julia. Winston thought she was a member of the thought police, but she isn't. He wanted to kill her, just because he thought that she was spying on him. Okay, that's not really Winston's fault, she was doing a good job at hiding her rebel mind. But she is just as corrupted as him. O'Brian. Winston somehow KNEW that O'Brian was like him, even though he is a member of the inner party. Winston had a dream where O'Brian tells him that "they will meet in a place where there is light". When they finally get to meet and talk, he tells him that "they will meet in a place where there is no darkness". Perhaps Winston was right about O'Brian. And finally, and most importantly, Mr Charrigton. This is what got Winston caught. He had bought the diary and the coral from him, he had rented a room where he and Julia could meet. All that because he had seemed so nice... Mr Charrington seemed like a lonely man because his "wife had died", and lived in the little shop. He had sang to Winston, showed him valuable pieces of art, lost information... But Winston could not have been more wrong about him. At the end of part 2, we learn that he is... a member of the Thought Police. Winston realizes all the changes in the old man... how his nose was smaller, how he had no wrinkles, how his eyebrows weren't bushy, and his hair is actually black, not white. Winston says that it is the first time that he is looking at a member of the Thought Police, that he knows of. If Mr. Charrington sold them, then Winston and Julia are in deeeeeeep trouble!!!!!!
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