ABSTRACT This thesis explores the R. v. Gladue (1999) decision and whether it is applicable to federal corrections and parole release. I outline a Cree relational approach—wahkotowin—that can be employed as a Gladue method of analysis to help us understand Cree history through a kinship relational lens. In Chapter 1, I share an overview of the teachings of wahkotowin, as taught by knowledge keeper and respected author Maria Campbell. With the help of her circle teachings diagrams, I outline our relationships and obligations to one another. I also outline the shattering of wahkotowin through imposed colonial and present-day policies, programs, and legislation, and the resulting inherited intergenerational trauma. Chapter 2 locates my personal story, exploring family and community history, and its connection with First Nations and Métis history on the prairies. Chapter 3 reviews the Supreme Court of Canada’s R. v. Gladue and R. v. Ipeelee (2012) decisions, the duty to properly consider the unique social history of Aboriginal peoples, and the applicability of Gladue to section 84 of the Corrections and Conditional Release Act. Chapter 4 outlines the qualitative data, including interviews with legal experts working with Aboriginal Legal Services of Toronto and the Gladue Court. The data explore best practices of interviewing, researching, and report writing necessary for obtaining Gladue evidence. In Chapter 5, I propose a Gladue-through-wahkotowin approach that explores how Gladue’s duty to consider social history evidence can be expanded to all phases of the criminal justice system, from sentencing to parole release, and can include a Cree relationship-based way of interviewing an offender, carrying out in-depth family and community interviews, attaining oral and documentary historical research, and applying a broad Indigenous approach to interviewing and the writing of Gladue Reports.