In Book 3, chapter 2, (pg 247) O'Brien is trying to convince Winston that he has a memory problem and that he keeps remembering things that didn't happen. He continuously tells Winston that his brain is messing things up and causing him to 'mis'remember what really happened. For example, O'Brien asks Winston who he believes Oceania is at war with. To this Winston replies, "Eastasia... I remember that until only a week before I was arrested, we were not at war with Eastasia at all. We were in alliance with them. The war was against Eurasia." But this is 'false', Oceania has 'always' been at war with Eastasia. This whole crazy mind warp parallels almost exactly with a scene from the movie 'Shutter Island'. ------ I am giving you a warning right now that what I'm about to say will give away the ending and most likely ruin the entire film for you ------- In 'Shutter Island', the protagonist, played by Leonardo Dicaprio, is a cop who travel to Shutter Island, where a mental institution is situated. He starts to go slightly crazy and thinks that everyone there is trying to convince him that he has lost his mind and indict him of being a patient. In reality he is a patient!!!!
This quote holds true for both Winston and Leo: "You have to humble yourself before you can become sane." Both individuals are wary and cynical of what they're being told, which makes it all the harder for them to change their minds and accept the 'truth'. Their beliefs in their own strength makes them develop scruples about giving in to what they're told.
For Winston it was necessary that he stop believing in his strength as an individual and the power of his memory. He needed to realize that Big Brother is paramount and that The Party is always right, has always been right, and will continue to always be right. He needs to eradicate all memories he 'thinks' he has that may disprove this.
For Leo, he needed to realize that he is no longer a great cop looking for the truth, that he is a murderer and a patient at a mental ward who has been living in a life full of delusion. This is extremely hard for him to do because as a cop he doesn't want to lose his sang-froid and be proven a credulous fool.
If you've seen the movie then my connections will probably make more sense to you. OR my connections may be shear folly because I came home and read this passage immediately after having seen the movie SO I probably was on a Leo-induced one-track mind type of thought process.
(If that did spoil the ending for you then I'm sorry, but the movie wasn't really all that great to begin with so don't feel too bad.)

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