The aim of this thesis is to explain the dichotomy between public perception of leadership and quantifiable measurement of leadership based on Information Measurement Theory, a method of utilizing deductive logic, and to identify and interpret the causes of such discrepancies as seen in the case of Steve Jobs. The general public perceives Steve Jobs to be an effective leader because he was visionary, entrepreneurial, charismatic and highly successful. However, these perceptions are not true indicators of leadership but rather qualitative interpretations of leadership without tangible evidence in support of this idea. An analysis of words found in multiple appearances of online articles relating to Steve Jobs and leadership revealed a variety of common factors associated with Steve Jobs' leadership, supporting a primarily positive viewpoint by the public. The thesis then identified how a new methodology of measuring leadership effectiveness based on quantitative data, known as the New Leadership Model, concludes Steve Jobs does not meet the criteria necessary to be considered a Best Value Leader, one who uses alignment rather than management, direction and control to achieve maximum efficiency within an organization. The discrepancies between public perception of Steve Jobs as a leader and the results of the New Leadership Model evaluation show significant variance. Potential rationale for these variances is offered in the thesis. In conclusion, the thesis argues that public perception will often differ from quantifiable measurement of leadership based on the interpretation of leadership by various groups and by the methods each group uses to identify characteristics of effective leadership.