The presence of street families among homeless youth has been a topic that has yet to be explored in-depth in Canada. Drawing on the 2009 secondary dataset which was carried out with a sample of homeless youth in Toronto, this research examines whether street youth have a higher likelihood of being in a street family based on their background experiences, situational adversities, and deviant peer associations on the street. The findings of this research show that youth in street families experience both past and current strains and develop deviant peer relationships more so than youth who are not members of street families. As evident by the results, theoretical integration is a possibility to achieve a comprehensive understanding of street youth crime and deviance. Both Differential Association Theory and Strain Theory provided analytic value when examining street youth membership in street families.