The revolution in 1984 was to liberate the proles. Did it work?

This question is somewhat tricky, because within 1984, there's the lingering question of whether any large-scale Revolution had ever been real at all. In Winston's own mind, he identifies with the Proles the sole hope of overcoming the oppression represented by Oceania. However, when discussing Winston's failed rebellion against 1984's dystopian state, we should remember the role and significance O'Brien himself played in encouraging it.
O'Brien, an inner Party member, organizes a meeting with Winston and Julia, claiming to be a member of a secret anti-government conspiracy, under the leadership of Emanuel Goldstein. O'Brien then sends Winston a book, providing the history and political realities which have shaped the world of 1984. It is through the influence of O'Brien that Winston starts taking steps toward meaningful sedition against Big Brother, but we should recognize that this entire conspiracy was itself manufactured, as we discover in the third part of the book. O'Brien was actually seeking out enemies of the State, which he could then break and reprogram through the use of psychological torture.
This raises one of the critical questions of 1984: is there any real organized resistance at all? That's a question that the book never really answers. Is Goldsmith a real person, rebelling against Big Brother, or is he an invention of the Party, a symbol used to manipulate the public? Can he be both? Was his book (the book O'Brien gives Winston to read) real, or was that too an invention? If so, can we trust anything the book tells us, about the history of Oceania and the world which Smith lives in? From that perspective, much of what one reads within 1984 is itself deeply unreliable—which is actually very appropriate, given the book's thematic content.
That being said, there are two final points worth making. The first is that, regardless of the larger conspiracy and revolution (which may or may not have existed), Winston Smith's own rebellion ends in failure. This is the subject of the third part of 1984, where Smith is captured by O'Brien, tortured, and broken. Against that, however, we should keep in mind the appendix: The Principles of Newspeak, which contains an academic article (and which does appear to have been written as an artifact within the world of 1984, albeit one produced much later). It begins as follows: "Newspeak was the official language of Oceania and had been devised to meet the ideological needs of Ingsoc, or English Socialism" (Orwell, 1984). For another excerpt from this article, see the following:

The purpose of Newspeak was not only to provide a medium of expression for the world-view and mental habits proper to the devotees of Ingsoc, but to make all other modes of thought impossible. (Orwell, 1984)

The inclusion of this last piece of academic analysis (which strikingly resembles the kind of writing one might find in a work of academic history) has led some readers to interpret this inclusion as a confirmation of Ingsoc's eventual collapse. From that perspective, while Winston Smith's rebellion ended in horrible failure, that larger dream may well have triumphed in the end.