Offenders and crime, especially those with a violent nature, are rife within the news media. However, little research exists pertaining to these offenders who are going to be, or nearing, their release on parole. This thesis aimed to extend prior literature by conducting two qualitative content analyses. The first included a general selection of Canadian parole-based newspaper articles from 2002 to 2022 in order to create a foundation of how parole is represented in the media. The second was an in-depth analysis that drew upon articles from a male offender (Larry Takahashi) and a female offender (Joanna Larson) to compare representations based on gender. This exploration uncovered four central themes, the types of crimes published, gender of offenders, age of victims, and the usage of certain language. The results of this study revealed several implications related to community attitudes, and public policy.