Brady Hawkes, The Gambler, receives a letter from his son indicating he needs help. This sends Brady to the rescue. Along the way Brady meets up with Billy Montana, a young man who thinks he knows everything about playing cards. Brady teaches Billy a few lessons along the way and they end up forming a strong friendship and team up together.

Natty Gann (played by Meredith Salenger) is a twelve year old Depression era girl whose single-parent father leaves her behind in Chicago while he goes to Washington State to look for work in the timber industry. Natty runs away from the guardian she was left with to follow Dad. She befriends and is befriended by a wolf that has been abused in dog fights, hops a freight train west, and is presumed dead when her wallet is found after the train crashes. Dad gets bitter and endangers himself in his new job. Meanwhile Natty has a series of adventures and mis- adventures in various farmhouses, police stations, hobo camps, reform schools, and boxcars.