The paper discusses some ontological and methodological issues involved in the studying of terrorist leaders. It starts from assessing the state of literature on terrorism in general and recurring challenges identified in it. In the many self-reflecting articles on the topic, the following issues are identified: the problem of the absence of an agreed definition; the poor quality of research; itinerant contributors; presence of ‘self-appointed experts’; unwillingness of researchers to commit to the study of terrorism; lack of barriers of entry into the field; problems with data; lack of cohesion and lack of clear methodologies; lack of intellectual progress. The paper moves on to discuss issues particular to the analysis of terrorist leaders. The trends identified follow the dichotomies present in social sciences in general, such as structure vs. agency and explanation vs. understanding. The paper shows fruitful avenues available in advancing on these roads. The last section discusses the value of different methodologies such as qualitative and quantitative analysis identifying the work done so far and assessing the possibilities for the future.