On their way to the club one evening, Bert and his chum Jack De Peyster see two policemen arresting a tough-looking guy. Jack is sympathetic but Bert laughs at him and says that the arrest is undoubtedly a good thing for society and takes exception to Jack's statement that a perfectly-innocent man can be arrested and thrown into jail and promptly accepts Jack's offer to wager $500 that he can be arrested and not commit a crime of any kind. Jack secures some old clothes, and dressed in these he enters a swell café much to the disgust of the other diners, one of whom notifies the proprietor, who phones for the police. The police arrive. Jack is arrested as a suspicious character and taken to the police station. From the station he sends a note to Bert telling him of his predicament, and asking him to come over and bail him out. Bert realizes he has lost the wager, but thinks to have some fun with Jack and denies all knowledge of him. Meanwhile Jack's valet has become alarmed at his master's absence and hurries to the home of Miss Livingstone, Jack's fiancée, and tells her of his fears. Miss Livingstone and her mother hurry to the police station and there see and identify Jack who is promptly released, and when Bert finally arrives at the police station, again he is arrested and thrown into a cell for playing pranks with the force. However, all ends well with the police captain a guest of the two boys at the club.