There is a quiet irony to be found in scholarly writings about the judiciary, which often center around high-profile jurists selected as the “great” judges. But there are great judges who do not receive or even want such widespread recognition, and who do not discuss their philosophy of judging—they simply focus on the job in front of them. Judges who operate with humility can often be very quiet about their legacies—brushing the issue off, as if uncomfortable with the attention. Anyone who knew Judge Richard D. Cudahy of the United States Court of Appeals for the Seventh Circuit will recognize this description. In some ways, that kind of reticence makes writing about his jurisprudence more than a little challenging. But in other ways, it invites us to examine what this “judges’ judge” exemplified as he worked at his craft. In reflecting on this, perhaps we can understand that craft more deeply.