Why does Winston cry at the end of 1984?

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In the final lines of 1984 by George Orwell, Winston sits in the Chestnut Tree Café watching endless streams of propaganda on the telescreen as he ponders his predicament. After rebelling against Big Brother by writing in a journal, consorting with Julia and attempting to join forces with the...

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In the final lines of 1984 by George Orwell, Winston sits in the Chestnut Tree Café watching endless streams of propaganda on the telescreen as he ponders his predicament. After rebelling against Big Brother by writing in a journal, consorting with Julia and attempting to join forces with the shadowy Emmanuel Goldstein, Winston is captured by the Thought Police. As Winston is physically and psychologically tortured by the Ministry of Love, he remains defiant and swears to remain loyal to Julia. O’Brien mockingly tells Winston, “What happens to you here is FOR EVER.” O’Brien’s warning is prescient. Winston quickly betrays Julia and caves to endless rounds torture and propaganda. After his ideological rehabilitation, Winston is permitted to visit the Chestnut Tree Cafe, a haunt of musicians, artists and former thought-criminals.

As stories of Oceania’s victories flash across the telescreen in the cafe, Winston is overwhelmed by emotion.

Two gin-scented tears trickled down the sides of his nose. But it was all right, everything was all right, the struggle was finished. He had won the victory over himself. He loved Big Brother.

Winston’s final tears demonstrate just how completely he has been “reformed” by his physical and psychological torture in the Ministry of Love. Winston’s tears are borne of genuine love and thankfulness toward Big Brother for helping him to win a victory "over himself." Orwell’s choice to end 1984 in this manner demonstrates the total power of The Party and underscores how deeply propaganda can shape an individual’s perception of reality. I hope this helps!

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Winston cries at the end of the book, in part, because he's been "broken" and, in part, because there is still a tiny part of him that knows he's not the man capable of free thought that he once was.  The part of him that used to have the ability to think freely and objectively is buried so deep inside that it can no longer completely surface, in fact, it is buried so deeply he is not even consciously aware of it.  If he were asked why he was crying he would probably respond that his tears were out of love for Big Brother.  And he would not be completely wrong because his tears are partly for BB.  That's how much he's been broken and how deeply buried is the Winston he once was.  He will never have the capability of thinking for himself again.

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