Winston Smith is the common man, easy for the reader to identify with, easy to sympathize with. Thirty-nine-years-old, he is frail and thin, and is employed as a records editor or propaganda officer in the Records Department at the Ministry of Truth. An Outer Party member, Winston leads a squalid existence in an apartment at Victory Mansions: he wears blue overalls, eats synthesized food – including black bread, bitter chocolate, and fake saccharine – rationed out by the Party, drinks industrial grade Victory Gin, and smokes Victory Cigarettes. He coughs violently in the mornings. He hates group exercising. He suffers itching and inflammation from a varicose ulcer above his right ankle – the symptoms of which grow worse the more sexually repressed he becomes, yet are alleviated once he starts the love affair with Julia. We’re already feeling sympathetic.
A thoughtful and observant intellect, Winston is very concerned with Party philosophy, and in particular its control of history through the manipulation of records, a process in which he participates daily. Resentful of the Party’s oppression of, um, everything under the sun, Winston spends much of his time accounting for the real past and musing on his rebellious tendencies. He is thankful for the alcove that escapes the watchful surveillance of the telescreen in his room, and starts a journal cataloging his anti-Party thoughts. He also enjoys strolling in the prole district, looking for connections to the past, Piña Coladas, and getting caught in the rain. The problem is, he’s not so great at doing anything about it.
More than anything, Winston seeks the unadulterated truth – and the only way to attain that is by rebelling against the totalitarian rule of the Party. From the moment he starts the journal, to the moment he consummates his love with Julia, to his first encounter with O’Brien, Winston holds on to his dream of freedom and independence. That unwavering individuality and the accompanying fervent rebelliousness are Winston’s strengths. However, combined with his unique sense of fatalism, they are also his downfall. Winston is extremely and deservingly paranoid, and his overriding belief that the Party will ultimately catch and punish him becomes gospel. Believing that he is helpless in evading his fate, Winston takes unnecessary risks, and is eventually (surprise, surprise) apprehended by the Thought Police.
And what’s up with O’Brien? O’Brien seems like an intellectual that can do things Winston can’t. He’s the cool kid. So you can imagine how much it stings for O’Brien to be the one that screws Winston over at the end. Talk about the ultimate betrayal. It’s a tragic element, which, not to beat around the bush, you can sometimes find in tragedies.