This study describes from an ontological perspective the foundation of freedom in two of Kleist's dramas. The novelty of this approach lies in the author's departure from the ontic considerations of freedom characterizing traditional Kleist scholarship. The present study advocates a de-construction of Kleist's concept of freedom back to its ontological basis: freedom is a cooperative enterprise of man and his situation. It is the author's contention that freedom in Kleist's works, rather than being defined by «a priori» categories, ensues primarily from the situation wherein it is being enacted. Man's relation to this situation is explored in a universal (Schroffenstein) and particular (Penthesilea) environment.