Does Winston literally die at the end of the book?
In the end, Winston describes being back in the Ministry of Love and a bullet entering his brain, but is this a dream or was he actually shot?
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No. He dies spiritually and psychologically at the book's end. His independent spirit is completely crushed, but he is left alive to love Big Brother. However, that image to which you refer is an indicator of how completely dead he is in these other ways: they might as well just shoot him. He's no longer any threat to them, since he's dead inside.
No, Winston is still alive. When the book concludes, Winston is waiting for the Party to end his physical existance. Since Winston has been re-educated, cleansed, and reborn with O'Brien's help in the Ministry of Love, he is now ready to die.
Julia is also in the same predicament.
Death is a desireable gift that the Party rewards all "healed" thought criminals.
He desires to be dead as a gift from the Party for his disloyalty previously throughout the book, which will show his "devotion and loyalty" to the Party.
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