In September 2015, Gayle Newland became the fourth person to be convicted of 'gender-fraud' since 2012 in the UK. This article offers a critical analysis of the media representation of these four cases and considers the extent to which the defendants are subjected to shaming and humiliation processes and presented as objects of disgust. The significance of media representation of legal cases is that it provides an insight into the ways in which legal discourses are interpreted, reinterpreted and often over simplified by those outside the legal profession. It highlights how legal discourses sit within a network of wider discourses and, therefore, illustrates the intertextuality of the law. Cheung (2014: 301) has suggested that, whilst the role of shame punishments in the criminal justice system has been subject to considerable academic scrutiny, 'social policing by shaming transgressions via the internet' has been under researched. This article will demonstrate that online news stories and the readers' comments that accompany them are important 21st century tools in the shaming and humiliation of those who have transgressed socially constructed gender norms.