John Blackwood

Jimmy Slocum, whose wealthy father continually pays his speeding fines and loses bets to him, wins a $1,000 bet with his father that Katherine Fowler, whom his father wants him to marry, does not love him. Jimmy then wins a $25,000 bet that he can keep from being arrested more than once in the coming year by getting a 12-month jail sentence for fighting in a bar, then sassing the judge.

Joe Smith Jr., the son of a millionaire, is challenged by his father to earn his own living instead of depending on his father's money. One year later Joe is broke, dirty, homeless and hanging out with other derelicts on a New York City park bench. A chance meeting with businessman Ned Stervens results in Joe being invited to stay in Stevens' house for a week, to make Stevens' point to his acquaintance Frank Overton---a shady stockbroker--that given a chance, even a tramp like Joe can better himself. Joe finds himself in love with Stevens' sister Lucy and unwittingly becomes party to a scheme by Overton to swindle Lucy out of her money.