The present study is the result of the attempt to subject the socio-economic world of energy to an analysis regarding a phenomenon called the ‘Black Swan’. This concept has been made popular by Nassim Nicholas Taleb, who has become a widely cited point of reference ever since the beginning of the financial crisis in 2007. The underlying assumption is, that against commonly held believe, it is not a long chain of incremental and statistically relevant events that constitutes history, but a seemingly insignificant number of outliers, or hence, ‘Black Swans’. Consequently, the study focuses on a critical examination of the strategic prediction models used in the energy business today, which are mainly based on driver based models. These models try to predict future price and value chain developments, ultimately searching for a strategic direction. This study questions this approach by showing that time and again similar predictions have been rendered obsolete by real developments. Based on the findings of this historical analysis, the study raises the question, whether it is possible to draw any practical conclusions for the future, discussing methods, which could provide protection from ‘Black Swan’ events.