This essay examines two little-known agents operating within the juvenile publishing market of the 1880s: the quality boys’ weekly Union Jack (1880–83) and one of its key contributors, Bernard Heldmann (1857–1915). Heldmann’s apprenticeship on the staff of the Union Jack prepared him for a successful second career as “Richard Marsh,” a bestselling author of gothic and crime stories for the adult market. It provided him with an acute understanding of the niche marketing of periodicals and genre fiction, the production of serial and short stories, and the uses of formula fiction. Yet, at the same time, Heldmann’s work increasingly challenged notions of “healthy” juvenile fiction by introducing elements of emotionality, homoeroticism, crime, and horror, most notably in his final serial, “A Couple of Scamps” (1882–83). Heldmann’s apparent popularity and business sense challenge the current scholarly assumption that turn-of-the-century boys’ fiction did not feature emotional male relationships.