Baseball card collecting carries with it images of idealized boyhoods in the sprawling American suburbs of the postwar era. Yet since the mid-1970s, it has grown from a pastime for children to a big money pursuit taken seriously by adults. This work employs interviews with collectors, dealers, and hobbyists to ask what this hobby tells us about nostalgia, work, play, masculinity, and race and gender relations among collectors. These interviews reveal the hobby’s alienating, lonely and unfulfilling aspects, and demonstrate the nostalgia experienced among collectors for the ideal childhood world many middle class white males experienced in the postwar years, when baseball card collecting was a form of play, not a money-making enterprise. The work links this nostalgia to anxieties about de-industrialization and the rise of the civil rights, feminist, and gay rights movements. It examines the gendered nature of swap meets as well as the views of masculinity expressed by the collectors: is the purpose of baseball card collecting to form a community of adults to reminisce or to inculcate young men with traditional masculine values? Is it to establish connectedness or to make money? Are collectors striving to reinforce the dominant culture or question it through their attempts to create their own meaning out of what are, in fact, mass-produced commercial artifacts?