For actor Claude Akins, "Winnings" was a winning reunion with a couple former castmates. Art Metrano had a recurring role as rival trucker Moose on Akins' 1974-76 series Movin' On (1974). Akins later had a recurring role as Sheriff Elroy P. Lobo on Greg Evigan's 1978-81 series B.J. and the Bear (1978). Akins' character proved so popular it was spun off into its own 1979-81 series, The Misadventures of Sheriff Lobo (1979).
For "Winnings," writer William Read Woodfield simply revisited and reworked his earlier story Odds on Evil (1966).