There are many ways to look at it. The last part of that question is the first thing to consider: does he fail or does he succeed? Further, what is he attempting to do in the first place, where success or failure can be debated?
To address the first part of the question, I'm not entirely sure that Winston has many strengths. If you think that he has failed at his goal, whatever that may be, his weaknesses are certainly part of the reason why.
Dave Becker
How do Winston's weaknesses lead to his failure in 1984?
One of Winston's biggest fears (weaknesses) is the fear of being without, i.e., the fear of deprivation which stems from his youth. Another of Winston's fears is rats. When Winston is being tortured, he is deprived of food and water, then the rats are introduced. This combination causes him to capitulate and turn in Julia.
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