The empirical foci of this paper are a content and discourse analysis of four years (1994 to 1997) of media reporting on 'homelessness' in The Ottawa Citizen, the premier, English language daily newspaper in the region. Examining these reports in juxtaposition with governmental and community-based reports from the same period has provided useful insights into how public opinion might be influenced to regard anti-homeless laws as more or less legitimate. This paper's approach was influenced by certain regulation theorists who argue that an examination of key discourses has the potential to enhance understanding about how economic, political and social restructuring is taking place, as well to shed light on how to intervene effectively at a variety of geographic scales in shaping its key elements. The results of the media analysis suggest that very particular messages are emphasized vis-à-vis "the homeless" the 'stubborn' unchanging nature of the problem, and the difficulties that housed citizens have in helping these passive, isolated, over-whelmingly white, male, substance abusers and contained (in the downtown) 'others'. They generally neglect or dismiss stories that might expose the demographic and geographic diversity of those who currently are homeless, and their complex and difficult past histories. When hints of such complexities are mentioned, they come with subtle messages about the deserving individuals who might be redeemed, in contrast to the hapless majority.