This article examines the leadership approach of the football coach José Mourinho, particularly of the relevance of the media for his top performance at Porto (2002–2004), Chelsea (2004–2007), Inter Milan (2008–2010) and Real Madrid (2010–2013). The perspective from which we analyse the work of Mourinho in that period, and his presence in the media, is based on what science calls the paradigm of complexity. This is a relational perspective which, in this case, means not only focusing upon the actions ‘central’ to the activity in question–the technique, tactics, physical preparation and so on–but, with particular relevance, detail and in an integrated fashion, also focusing on the media and the cultural context in which the activity takes place. Key to the transformational work of José Mourinho is his presence in the media, the managing of fame, the challenges and ambitions of the players, the fans and the general public. At stake is a personification of a global system of significance.