There is an ancient antagonism of philosophy towards poetry from the time of Plato that still casts its shadow over philosophical practice. In terms of the univocal standard in philosophy's critical discourse and its hermeneutic assumptions in philosophy. This thesis undertakes a re-assessment of poetry by returning it to its proper hermeneutic and existential milieu, in turn promoting a deeper appreciation of philosophical possibility from the re-introduction of poetic discourse into philosophical enquiry. Employing cross-between a Hegelian and Kierkegaardian dialectical method, this thesis situates insights gained from literary critical theory into the context of Existentialist and Personalist philosophy. Kierkegaard's dialectic has proved an appropriate methodology for a philosophy of poetry and poetic experience in its ability to rigorously maintain the tension between negatives and in its organic development of transcendent dialectical stages of increasing explanatory power, without the necessity required by Hegel. However, as Hegel said, truth is expressed in the whole, not merely encapsulated in its end product. A parallel discursive stream critically analyses poetry by Australian poet Francis Webb to complement and ground the philosophy in an authentic poetic voice. The consequent integrated structure fashions a negative mould making possible a further dialectical act in outlining an ethics of the poetic spirit in the thesis conclusion.