Youth advocates employed in a school-to-work program in an inner-city public high school promoted the college attainments of low-income Black students through the production of cultural and social capital. Analysis framed by cultural reproduction and production theories explicate how they inverted the ideological aims of the program; redefined their roles as "surrogate" middle-class parents; generated cultural productions through reality therapy; and created useful links to social resources and networks. Youth advocates changed the educational trajectory of some students. But there were other students who used cultural and social capital in productions that kept them closely tied to their families, neighborhoods, and local workplaces. (Contains 3 endnotes.)