In reviewing the influence of information systems on today’s organisations, it becomes evident that top managers play a critical role in their inevitable success or failure. Yet, despite these systems strategic relevance many studies reveal a dichotomous relationship between ‘management’ and ‘information systems’, a relationship kept polarised by organisational myths resulting in the emergence of differing community perspectives. Such division is borne out in the increasingly high rates of information systems failure within practice. As strategic stewards of the organisation, top managers are noted to play a vital role in supporting information systems. Support is said to be a multifaceted concept requiring both thought and action. This paper in reviewing the information systems management literature attempts to unravel the mystery that has shrouded this topic over the past five decades. The journey seeks to provide top managers with a roadmap before Crossing the Rubicon to support the introduction of information systems.