High-profile sports people and their use of drugs and alcohol have featured prominently in the news in the recent past. From AFL star Ben Cousins' suspension for possession of illegal recreational drugs (March 2007), rugby league player Andrew Johns' admission to a long history of drug abuse (October 2007), Nick D'Arcy's charge for assaulting fellow sportsman Simon Cowley (March 2008), and cricketer Andrew Symonds' admission of excessive drinking (November 2008), the media has had no shortage of events to cover. Studies (such as Biskrup and Pfister, 1999; Anderson and Cavallaro, 2002; White and O'Brien, 1999; Stevens et al., 2003) have shown that sports stars are held up as role models by some young people, particularly males. Other studies (such as Paccagnella and Grove, 1997) have shown that sports stars' transgressive behaviour affects how young people perceive those sports stars, however, there seem to be no studies to date that examine the way sports stars are portrayed in the media the events of their transgressive behaviour. This chapter seeks to begin to fill a gap in the literature on sports stars and their celebrity status in the public eye, by focusing on the print media coverage of Ben Cousins during the period of time when he was suspended from football due to drug taking and erratic behaviour off the field. This chapter aims to begin to unpack the way sports stars who transgress are packaged for the public, and in particular, for adolescents. As such it uses an Appliable Linguistics Framework to address a real-life problem, illuminating how the language choices that are made construe particular versions of reality.