A growing sense of alienation and a fear of disaster affect our daily lives as extreme weather events, superbugs, and political upheaval increasingly become part of experienced, perceived, or dreaded reality. We seem to inhabit a world turned upside-down. Among Jews, the period from the sixth century B.C.E. to the first century of the Common Era was comparable to our own in terms of mood and the range human responses. In this critical watershed period following Babylonian conquest, the biblical writers tried to make sense of and cope with the trauma of war, dislocation, forced migration, ecological disaster, and colonialism. They sought to explain the situation in which they found themselves, offered ways of coping, and expressed hopes for utter transformation so that the troubled world would be replaced with a new and better reality. We will read from the work of the great exilic prophets in the books of Jeremiah, Ezekiel, and Isaiah, examine some of the so-called “wisdom” traditions in the Hebrew Bible and Apocrypha exemplified by Job, Ecclesiastes, Proverbs, and Tobit, and, finally, explore the phenomenon of Jewish apocalyptic in works such as Daniel, the Dead Sea Scrolls, 4 Ezra, and 2 Baruch. The problems of these authors and their responses, which laid the foundation for critical themes in Christianity and Judaism, strike the reader as incredibly contemporary. Our work in this ancient material will be enhanced by relevant examples from our own times.