This Article compares the years of experience that preceded each Justice‘s appointment to the United States Supreme Court. This Article seeks to demonstrate that the background experiences of the Roberts Court Justices are quite different from those of earlier Supreme Court Justices and to persuade the reader that this is harmful. To determine how the current Justices compare to their historical peers, the study gathered a database that considers the yearly pre-Court experience for every Supreme Court Justice from John Jay to Elena Kagan. The results are telling: the Roberts Court Justices have spent more pre-appointment time in legal academia, appellate judging, and living in Washington, D.C., than any previous Supreme Court Justices. They also spent the most time in elite undergraduate and law school settings. Time spent in these pursuits has naturally meant less time spent elsewhere; the Roberts Court Justices have spent less time in the private practice of law, in trial judging, and as elected politicians than any previous Court. Having demonstrated that the Roberts Justices are outliers across multiple studied experiences, this Article argues that the change is regrettable for multiple normative reasons.