Discuss the Party’s strategy regarding Winston. Why isn’t Winston arrested earlier, when O’Brien already knows so much about him?
The Party seeks to obtain as much information as possible about Winston before arresting him. Winston, therefore, has no way to deny or object to the charges brought against him. By posing as an ally and encouraging Winston to read Goldstein’s banned book, O’Brien acquires crucial information about Winston. Mr. Charrington, another agent of the Party, ensures he has Winston and Julia’s trust before setting them up. When Winston is arrested, all his crimes are well-documented, which in turn allows the Party to deal with him harshly and with impunity. In the end, the Party successfully breaks Winston’s resistance, and he poses no threat to the regime.