Being the only female Newsie is a tough life. Constantly surrounded by teenage boys who can be overprotective to the extent she feels like she has no freedom. Heather Kelly, A.K.A. Teddy, little sister of the infamous Jack Kelly, finds herself in an unusual predicament when she sees her long time newsboy associate, Racetrack Higgins in a different light. Racetrack Higgins, the only boy who didn't treat Heather like the little sister she was to every other newsboy.