As the title suggests, this essay is a postmodern and autobiographical analysis of the three detectives in Paul Auster´s widely acclaimed 1987 novel The New York Trilogy. The focus of this study is centred on a comparison between the three detectives, but also on tracking when and why the detectives devolve into madness. Moreover, it links their descent into madness to the postmodern condition. In postmodernity with its’ incredulity toward Metanarratives’ lives are shaped by chance rather than by causality. In addition, the traditional reliable tools of analysis and reason widely associated with the well-known literary detectives in the era of enlightenment, such as Sherlock Holmes or Dupin, are of little use. All of this is also aggravated by an unforgiving and painful never-ending postmodern present that leaves the detectives with little chance to catch their breath, recover their balance or sanity while being overwhelmed by their disruptive postmodern objects. Consequently, the three detectives are essentially all humiliated and stripped bare of their professional and personal identities with catastrophic results. Hence, if the three detectives start out with a reasonable confidence in their own abilities, their investigations lead them with no exceptions to a point where they are unable to distinguish reality from their postmodern paranoia and madness. And in the meantime, no crime is resolved and no social order restored. The autobiographical back drop of the three detectives and protagonists in the three novellas is the author´s own life in the late seventies and early eighties. In that sense the three protagonists all illustrate the parallel lives the author could have had, if chance and trivial every day decisions had not turned Auster´s life around, at certain critical junctures during the darkest moments of his life in connection with the painful divorce from his first wife.