Judgment is, among other things, a characteristic capacity of certain intelligent organisms, and it is thus natural to turn to empirical psychology to investigate it. Our initial set of case studies are accordingly drawn from psychology and its history. In particular, I consider in this chapter three attempts to tackle the problem of judgment experimentally. Two cases come from modern neuropsychological research; the third is by now ancient history: the eighteenth-century psychological experiments due to David Hume. The three experimental approaches diverge dramatically in their methodologies and in their conception of psychology, yet each exhibits the pattern which is the subject of this book: the entanglement of logical, psychological, and phenomenological constraints in the theory of judgment. My discussion aims both to document these entanglements and to show how, in at least two cases, they lead to experimental failure. But I also seek to extract positive results, exhibiting a substantive logical constraint on the theory of judgment (Hume's content identity condition) and a variety of patterns whereby experimentalists have sought to integrate the various faces of judgment.