Consider the logic of O’Brien’s comments. Has Winston acted according to his own free will, or has his fate been predetermined from the...

In a way, both. Winston did act of his own free will in
choosing to set himself "up against the party," and his fate was determined by that
choice. It is ironic in a way, because the focus of the novel is on the concept of
control. Winston wants desperately to have the free will to love and think and act as he
chooses - to control his own life - yet that "free" will is lost to him. He sees the
signs that say "Big Brother is watching you" and knows the "thought police" might
suspect him at any moment, and that the "telescreens" monitor his every move. Winston
bemoans the disappearance of his family members, talks at length about people
disappearing, and yet, still chooses to exert his free will to initially write in his
journal. He knew he may suffer the same fate, but could not resist the most basic human
desire to control some aspect of his own life.