The Lemon Drop Kid (Bob Hope), a New York City swindler, is illegally touting horses at a Florida racetrack. The Kid touts across a beautiful woman intending to bet $2,000 on a horse named Iron Bar. Rigging a con, the Kid convinces her to switch her bet, but learns that she was betting for boyfriend and notorious gangster Moose Moran (Fred Clark). When the horse finishes dead last, a furious Moran demands the Kid pay him $10,000 (the amount he would have won) by Christmas Eve, or the Kid "won't make it to New Year's."