Other people may have other answers, but to me, there are
two really clear bits of evidence that show that Winston sort of sabotages himself. I
would say that we see this first when he decides to rent the apartment over the store
and second when he decides to trust O'Brien. Both of these would seem to be really rash
acts in this society.
In both cases, Winston is rather
blatantly committing acts that can get him killed. You would think that someone in this
society would suspect that everything is a trap. Why is this apartment available to
rent? Why does it have no screen in it? It seems too good to be true and Winston ought
to see that. The same goes for O'Brien. It seems naive in the extreme to believe that
this guy is really part of this subversive group.
I think
that Winston is not suspicious enough of these "opportunities." To me, that shows that
his fatalism is self-fulfilling -- he's purposely doing dumb stuff that will get him
caught.
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