Still writing in his diary, Winston records his belief that the Party will be overthrown by the proles, who make up 85 percent of the population of Oceania. The Party makes no attempt to indoctrinate them, and promiscuity among them goes unpunished, because the Party considers them to be too stupid to be dangerous.
Winston's first statement of belief in the possibility of revolution by the proles. He notes the paradox that the proles cannot rebel until they become conscious, and they cannot become conscious until after they have rebelled.
From a children's textbook, Winston copies out a passage describing capitalism. He can't tell how much of the passage is lies, but he suspects that life in Oceania may have been better before the Revolution overthrew the capitalist system, though the Party claims that the standard of living is higher and that people are happier and live longer.
Suspicious of the Party's claim that life under INGSOC is better than before, Winston makes further efforts to learn the truth about the past. The children's book is another example of propaganda.
Winston recalls finding a photograph eleven years earlier of three men—Jones, Aaronson, and Rutherford—former leaders of the Revolution who had been exposed as traitors, imprisoned, tortured, released, and eventually rearrested and vaporized. Winston remembers seeing the three at a bar, the Chestnut Tree Café, weeping sentimentally into their gin. The photograph Winston found proved their innocence, and showed that their confessions had in fact been extorted. Winston regrets having destroyed the photograph out of fear.
This memory prefigures the final chapter of the novel in which Winston, broken in torture by O'Brien, weeps sentimentally over his love for Big Brother while drinking gin at the Chestnut Tree Café. At this point neither Winston nor the reader knows why the men are weeping, but the reason will become clear by the end of the novel.
Winston is mystified by the Party's reasons for continuously falsifying the past, and horrified that what Party ideology amounts to is an outright denial of external reality. To the Party, he realizes, common sense is the ultimate heresy.
Winston becomes aware that he is writing the diary to O'Brien. Though conscious of his own intellectual limitations, he still believes that he is right and that the Party is wrong. The freedom from which all other freedoms follow, he decides, is the freedom to see reality for what it is, to say that two plus two make four.
Although he believes that the Party is evil, Winston desires confirmation of this from O'Brien, whom he views as his intellectual superior. Ironically, it is O'Brien who forces him to see that 2+2=5.