This article draws on data generated in semi-structured interviews to describe changes in social capital in the form of social networks across two generations of male school leavers. The article achieves this by comparing and contrasting the school-to-work transitions of eleven poorly qualified males, who left school in the late 1990s, to the transitions made by their fathers in the years between 1955 and 1980. The data show that the value of the social networks available to today's school leavers has declined in comparison to the value of the networks that were available to their fathers. It is argued that the decline in the value of social networks has contributed to risk and uncertainty in school-to-work transitions.