Winston's fatalistic from the get-go, and with good reason too. There's simply no way that he, or any other individual in Oceania, can ever prevail against the forces of this totalitarian state. But Winston's nothing if not courageous. And if he's to go down—which he knows is inevitable—he'll go down fighting. In a state where everyone is under suspicion, and all Outer Party members like Winston are under almost constant surveillance, it doesn't take much for someone to be slung in a prison camp or vaporized. So Winston probably figures that if this is indeed his fate in any event, then he might as well show some defiance to a regime which he cordially loathes.
Winston's innate fatalism is almost like a death-wish. It leads him on to take increasingly dangerous risks, almost guaranteeing himself a trip to Room 101. Winston knows from the very start that he's guilty because in Oceania everyone is guilty of something, whether it's a thought-crime or, more rarely, a deliberate act of sabotage. It's just a matter of time before they get caught. And Winston's no different. His illicit tryst with Julia and his clandestine dealings with O'Brien merely compound his guilt. Winston was always destined to destruction, but his acts of willful defiance merely hasten the process.
Winston believes, like everyone in Oceania, that the Thought Police are both omniscient and all-powerful. He has no illusions about being able to remain undetected as a "thought criminal," probably from even before he begins recording the heretical thoughts in his diary. If there is any hope—hope that the totalitarian regime will be destroyed—it lies in the proles, he repeats to himself, not in people such as himself who are basically descended from the old middle class in capitalist societies. It is ironic, because the proles are the bottom of the hierarchy; they are the people with the fewest rights, though in Oceania no one has any rights. Winston also tends to see hope, if it exists, in abstract forces, like the uninhibited sexual drive of someone like Julia. But he paradoxically links his own hopelessness to the "subversive" affair he has with her. Once he and Julia have gotten together, he sees his doom sealed even further. It is symbolic that just before they are arrested, they repeat the words "we are the dead," which are then mocked by Mr. Charrington. Once he is taken into custody, O'Brien confronts Winston by saying, "You knew this, Winston." There really was no reason for Winston ever to have believed that O'Brien was a subversive, and Winston realizes this in this moment, if not before. That he even thought to risk discovery by going to O'Brien with Julia in the first place was a desperate move, something Winston knew would end with his own destruction. But it is that very hopelessness that caused him to take the risk: he knew he was finished anyway. This is the clearest evidence that Winston realizes from the start that he will be destroyed.
Winston understands that his destruction or defeat is inevitable from the very start of the novel. Shortly before the action of the novel begins, Winston purchases a diary from a store in the prole's district. He carries it home "guiltily," because he knows that even buying it was a suspect act. As he opens it and prepares to write, he realizes that his act of writing will carry the following consequences:
if detected it was reasonably certain that it would be punished by death, or at least by twenty five years in a forced-labour camp.
From the start of the novel, Winston understands that he is heading down the path of destruction. While hoping against hope he will escape detection, Winston repeatedly says to himself and to Julia that this can only end one way: with their destruction.
Given the trajectory of the novel, Winston is correct to be fatalistic. He is detected, arrested, and broken. The novel shows the state's power as overwhelming. Its surveillance is everywhere: in the woods, in his flat, and in the room over Mr. Carrington's shop. There is no escape.
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