Trakl was the master of transfiguration and poetic enigma. His poetry uses a very specific number of colours (black, purple, blue), strikingly simple rhyme and – at times obstinate – repetition to unmatched effects. The expressive quality of his poetry never amounts to dogmatic expressionism but relates, and reflects, the deeper qualities of introspection. It tries to identify the very roots of expression in the troubled human existence. His poetry originated in feelings of guilt (often connected with the biographical fact that he had induced his sister to the misuse of drugs) and utter desolation. We have seen already that to him the self-destruction of occidental culture was a certainty years before the outbreak of World War One. This chapter discusses whether it can be argued that Trakl’s poetry reflects, to a certain extent, an anticipation of the horrors that became manifest and unbearable to him already in the very first weeks of this European tragedy with disastrous global implications.