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Criminologists argue that masculinities are often connected with delinquency as a way to prove masculine competence. Based on the argument, this exploratory qualitative study investigates how male delinquents' masculinities influence their theft. The data consisted of in-depth interview transcripts with 10 male delinquents and official records collected at a probation office in Chungbuk area in Korea and at a juvenile correctional facility in Minnesota in USA. The qualitative data analysis revealed that the association between male adolescents' theft and masculinities may be fairly clear. The delinquents experiencing inability for achieving the long-term goals of hegemonic masculinity in class and educational system tended to adhere to a narrow conception of masculinity that stresses material possessions as a defensive strategy to counter their feelings of marginality. And they tended to depend upon theft to show their masculine competence through economic competence, risk-taking, and intelligence. This study findings suggest the development of programs that protect male adolescents from adherence to stereotyped masculinity, which is associated with theft.