This chapter considers Heidegger’s “two-handedness” on the issue of realism versus idealism: on the one hand, an apparent realism about entities, while on the other, an apparent idealism about being. Interpreters tend to resolve the tensions such two-handedness engenders by giving one side or the other the upper hand. Kantian approaches to Heidegger privilege idealism, other readings favor realism. The latter readings neglect Heidegger’s own rather mocking remarks directed at those who fear idealism as “the foul fiend incarnate” and favor instead what he calls a “blind realism.” Properly understood, such remarks point toward a position beyond both realism and idealism, a position akin to, but importantly different from, Quine’s naturalism. Quine’s imagery of “working from within” and “mutual containment” provide models for a more evenhanded approach to the issue of realism and idealism. Moreover, they help us to understand Heidegger’s principal aim of rejecting both positions.