As the student deliberates on how he or she would act in the dilemma in which Officer Wells finds himself, consideration should also be given to the personality traits of 'Silky Bob.'

As Jimmy's old friend stands in the doorway of what once was a 'Big Joe' Brady's restaurant, he tells the policeman on the beat that he is waiting for Jimmy Wells, "my best chum, and the finest chap in the world" who was like a brother to him. The friend adds that when he left for the West, he and Jimmy agreed to meet in twenty years no matter what transpired during those two decades.

By the fact that Bob has agreed to meet his friend "no matter what transpired" in their lives during those twenty years indicates that Bob is willing to accept his old friend as he finds him when they meet again. This moment seems like one that presents an opportunity for Officer Wells to introduce himself and to make the arrest. But he does not; instead, Jimmy Wells later writes his letter which the plainclothes policeman hands to Bob after making the arrest that reads, "Somehow I couldn't do it [the arrest] myself..."

It is with the interpretation of this line that the reader determines the character of Jimmy Wells. Is it kindness not to arrest Bob and humiliate him since Jimmy has been "like a brother to him," or is it cowardly and selfish to avoid the confrontation? Then, too, the reader will want to consider how Bill would react to Jimmy's arresting him in contrast to the plainclothes officer's doing so. With a risk-taker like Bill who is adventurous to go out West, it seems likely that he would find Jimmy's having another policeman make the arrest somewhat cowardly.