Nathaniel Hawthorne's The Scarlet Letter has much to teach psychoanalysts and psychotherapists. Perhaps no other American novel lends itself so well to an exploration in depth of the dynamics, conflicts, and defenses characteristic of shame. While most commentators on The Scarlet Letter have assumed Hester Prynne's pain to be shame-based, and the Reverend Dimmesdale's to be guilt-based, a rather different interpretation is proposed namely, that both are afflicted with shame, but that Dimmesdale's is more unbearable than Hester's because more conflictual, less representable, and less easily used protectively. Dimmesdale's shame is at once deeper and more toxic. What “deeper” and “more toxic” mean in the context of shame conflicts (including conflicts to which feelings of shame give rise) is explored.