This article reflectively applies measurement tools to gage whether a renowned financier and champion of shareholder capitalism, in 20th century business history, might be categorized as a corporate psychopath. The article examines aspects of the career of the outstanding financial investment manager, Bernie Madoff. Psychopaths and corporate psychopaths are defined as background to the article. Gauges of corporate psychopathy and psychopathy are outlined which could be modified by market research companies to identify corporate psychopathy in organisations as a way of aiding investment decisions into such organisations. The current article concludes that insolvencies such as those at Madoff’s investment company, have been distinguished by CEOs being present who were simultaneously the lauded agents of financial market capitalism and who embodied the traits of the corporate psychopath. The examination of potential corporate psychopaths using this historical methodology helps inform ideas about what the effects of psychopathic leadership may be within economies and gives new insights into the reasons for the greed, risk taking, and unethical practices found in financial markets. Findings support the accepted view that corporate psychopaths can be discovered in senior roles in the financial services sector. This current paper provides new avenues for research offerings from market research companies. For example, business to business researchers could undertake research to identify firms more likely to be longitudinally viable, sustainable and less likely to collapse (i.e., non-psychopathic firms). Investment companies like pension funds could use such research to identify firms that are less risky, more ethical, better led, and therefore safer to invest in.