Answer:Since Chapter 8, Pip has been expecting (or rather hoping) to move up in life and become worthy of Estella. When he received his money from his unknown benefactor, Pip automatically assumed that this was Miss Havisham's way of helping him become a gentleman, and thus, marry Estella. In Chapter 39, Pip discovers that his benefactor is none other than the convict from the start of the book. It is at this point that Pip realizes that his expectation of someday being worthy of Estella will never come true. He has money, but it is ill-gotten money in his opinion. And his assumption that Miss Havisham wanted Pip with Estella has been proven wrong. It is at this point that Pip realizes that the one thing he has been working towards (Estella) will never be. Pip also realizes that in his pursuit of Estella he has trampled on his best friend Joe. Chapter 39 essentially crushes all of Pip's expectations of being a gentleman. It is after this chapter that Pip realizes that no matter how much money he has, he will never be worthy of someone like Estella. It is also at this point that Pip starts to realize that his expectations may have not been worth all he has sacrificed in life (friendships, home, his true self).
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