For Dexter, seeing himself as "newer and stronger" than the wealthy people to whom he compares himself is in reference to Judy Jones. As he recognizes the "men who had already loved Judy Jones," Dexter rationalizes that he can succeed where these men have failed. In his mind, Dexter will be more successful in his wooing of her due to his stock of strength. He understands that these previous suitors were wealthy, reflective of "old money." Dexter, though, sees himself as a form of "new money." With his growth and emergence into wealth from humble beginnings, Dexter believes that he is "newer" and "stronger" in comparison to the traditional wealthy people that have failed to capture Judy Jones' attention.
For Dexter, this rationalization is the basis of why he thinks he can hold onto Judy. He believed himself to be made differently, offering her something that previous men could not. In this, one can see the optimism that Dexter has towards his "winter dreams." This hope and unbridled sense of opportunity serves as his motivating force, rooted in the idea that he, Dexter, is "newer and stronger."
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