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I think that the premise of the question might need to be refined. I think that Dexter's love of money and status causes him to embrace Judy Jones. I don't see Judy Jones as standing in the way of Dexter's wealth. Remember that Judy Jones is the woman who asks Dexter during one of their first conversations, "Are you poor?" Dexter's love of money and his embrace of materialism are what enable him to envision Judy and enable him to win her over, if nothing more than for a period of time. I don't think that Dexter's desire for money separates him from Judy. If anything, his hunger for money and the trappings of wealth makes him more eligible for her. It is Fitzgerald's desire to create a sad and rather disgusting conception of the American Dream where materialism becomes the driving force for "Winter Dreams," a sense of beauty and the ornate only to be undercut by a sense of the corruptible and that which is transitory. It is here where Dexter's coveting of Judy and of money reaches its natural end. When he weeps at the end, he weeps for how contingent such a vision is, the ultimate recognition of temporal failure in the vain hope of what might be. Money and materialism become a part and an intrinsic measure of success in this pursuit of Judy.
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