As a cisgendered White male who emerged from a decidedly working-class family, the national fantasy of achieving the prototypical “American Dream” (i.e., working a white-collar job, getting married and raising children in “good” neighborhoods, and an opportunity at a better quality of life for our offspring) has long been socialized into my life. However, as I have reached the supposed mountaintop both personally and professionally to become part of what Stewart terms the “New American Aristocracy”—that is, the so-called 9.9%—so too have I become increasingly discomfited by that which it represents. In this autoethnographic narrative accounting, I offer a critical yet necessarily confessional look back at the concessions, complications, and privileges my family’s subjective performances of Whiteness have revealed about the ever-growing toxic class divide in the United States. The results of our exchange will and cannot be perfect, but, hopefully, a step in a better direction.