Through an analysis of a number of 'rogue trader' events that occurred over the last two decades, some light will be shed on the underlying causes of the 'rogue trader' phenomena and the financial market collapses that seems to plague financial systems, with growing regularity and intensity. The perspective I offer will focus on the role of structural factors that facilitated the development of a culture of extreme opportunism present in the environment in which these so called 'rogues' operated. This culture played a motivational and facilitating role for those engaged in the headlong pursuit for profits, through investing in sub-prime based securities and derivatives. Coupled with massive incentives of a monetary and non-monetary nature providing fuel for uninhibited opportunism, a meltdown of global proportions was inevitable. Similarly I will highlight the tell tale absence or ineffectiveness of those factors that could or should have inhibited extreme opportunistic conduct.