In "Winter Dreams," does Dexter Green succeed or fail in achieving his goal?
Throughout this excellent short story we see that Dexter Green is impelled to make a success of his life through earning money and gaining the glamour and confidence of the rich, as personified in Judy Jones. Of course, for him, his goal or aim is symbolised in the person of Judy Jones herself, and throughout the story at various places Judy as a character is explicitly related to wealth and the goal that Dexter has for his life:
Judy Jones, a slender enameled doll in cloth of gold: gold in aband at her had, gold in two slipper points at her dress's hem.
Note the way in which gold is repeated and associated so closely with her character. It is clear that the reference to gold links in which Dexter's winter dreams and the wealth he longed for and achieved, but also found wanting. Judy represents or symbolises elusive glamour, that Dexter can never quite attain. It is highly interesting that at the end of the story, when he hears how Judy Jones has lost her looks, he feels that his dream is lost and has not been achieved. Although he is rich and successful, still that is not enough for Dexter, as he expresses in the last paragraph:
"Long ago," he said, "long ago, there was something in me, but now that thing is gone. Now that thing is gone, that thing is gone. I cannot cry. I cannot care. That thing will come back no more."
This shows that, in Dexter's opinion at least, he has not achieved his goal and his attempt to pursue it has only resulted in a feeling of disappointment and loss.