This thesis examines three legacy media outlets' (Toronto Star, Globe and Mail, and National Post) digital coverage of the Coastal GasLink conflict between January 1 and March 15, 2020. This thesis aims to understand how Canada's largest daily newspapers portray Indigenous communities, particularly during times of conflict with the government. Through a content analysis, a review of past coverage as examined in existing academic literature, as well as through interviews with academics, experts and critics, this thesis uncovers minimal change in coverage patterns over the past several decades. Legacy media still relies on stereotypical portrayals of Indigenous communities and often does not present the larger context of a conflict that would provide better information for readers to interpret. Ultimately the thesis addresses some of the questions about how legacy journalism is built and conducted overall and argues that it does not work to best portray Indigenous issues and communities.