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Based on multiple in-depth interviews with two former juvenile offenders who report having extensive involvement in the juvenile justice system for many years, this study examined how they interpret and define their juvenile offending. The study makes use of a qualitative research method using a collective case study approach. A corollary purpose of the study was to determine if findings could be couched in Robert Agnew’s (1992) General Strain Theory. The article focuses on several themes that emerged from the interview data. These themes reveal several sources of strain in participants’ lives at the time of their offending that are congruent with General Strain Theory.