Even though Winston's life is replete with misery and pain, Orwell allows him a brief time of happiness and love. During this time, there is hope for Winston, and subsequently, hope for the future. But Orwell makes certain that there is no happy ending. Totalitarianism does not permit such an ending; Winston must be crushed. If Winston were to escape, Orwell's agenda of showing the true nature of totalitarianism would have been lost.
Readers identify so closely with Winston because he has individuality and undying self-determination. Winston embodies the values of a civilized society: democracy, peace, freedom, love, and decency. When Winston is destroyed, these things are destroyed with him, and so goes the reader's faith that these values are undying and a natural part of being human. Winston represents the struggle between good and bad forces, and there is no mistaking where the lines are drawn.
Ultimately, Winston loses his spirit and his humanity, the two characteristics that he fought so hard to keep. Orwell insists that Winston's fate could happen to anyone, and it is for this reason that Orwell destroys Winston in the end, so that the reader may understand Orwell's warning and see that the society of 1984 never come to pass.
