Why does Winston Smith hate the Party in 1984?

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In 1984, Winston hates the Party and detests Big Brother. Winston, an intellectual and naturally curious individual, is frustrated with the stifling nature of the Party's intellectual policies—notably rewriting history, which is ironically exactly what Winston does for a career.

Being older and able to remember the times before the Party's complete control, Winston knows what the world was like and could be like without Big Brother's control. He is dissatisfied on an intellectual level because he cannot convince himself of the lies and constantly shifting history of their country. He is very intelligent and seditious in that regard, simply because his own natural curiosity prevents him from shutting off his brain and accepting the lies of the Party out of hand.

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As part of the older generation, Winston can still recall a time before the Party and Big Brother. Naturally, it is easier to brainwash and control younger generations who have nothing to compare the current system to. In Winston's case, it's harder to keep him in line because he still remembers something better.

Additionally, Winston has character traits that cause him to resist the conformity and intellectual stifling that is part of the Party. Compared with Julia, who is concerned with more selfish pleasures, Winston's resistance to the Party comes from a place of deep, intellectual rumination. He is naturally curious and has a streak of rebelliousness that causes him to test the limits of the Party's power by doing things like writing "down with Big Brother" in his diary. 

Naturally, a person like this would bump up against such a restrictive system eventually, no matter the personal danger it would put them in. 

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