The Trolley Problem is not only one of the most widely discussed puzzles in moral philosophy. It is also one of the most controversial with respect to its perceived importance. At the one end of the spectrum there are those who consider it to reveal facts that belong at the very center of our moral understanding. At the other end of the spectrum there are those who consider it to be an example of contemporary philosophy at its most pointless. In this chapter, I critically address this dispute by tracing the discussion of the problem from its earliest formulation on the work of Philippa Foot, Judith Thomson, and Frances Kamm. Then I discuss a number of the most important criticisms of these discussions, drawing on the work of Barbara Fried. In doing so, I describe not only the actual causes of the problem’s continuing interest but also the underlying justification and rationale for that interest to which that history gives evidence.