Jimmy is the more admirable character of the two men in "After Twenty Years." Jimmy displays many admirable qualities, including intelligence, integrity, authority, and compassion. He makes Bob seem flashy and superficial. When Jimmy realizes that his old friend Bob is the man wanted by the Chicago police, he is faced with a dilemma. He doesn't want to arrest a friend who thinks so highly of him and has come so far to meet him...
Jimmy is the more admirable character of the two men in "After Twenty Years." Jimmy displays many admirable qualities, including intelligence, integrity, authority, and compassion. He makes Bob seem flashy and superficial. When Jimmy realizes that his old friend Bob is the man wanted by the Chicago police, he is faced with a dilemma. He doesn't want to arrest a friend who thinks so highly of him and has come so far to meet him after twenty years. On the other hand, Jimmy has a sworn duty to uphold the law, and it is obviously his responsibility to arrest Bob. He solves that problem with intelligence by ascertaining that Bob will be standing there in the doorway for about a half-hour and then turning the job of arresting him over to another officer. Jimmy shows that he experiences regret when he tells Bob in a note:
Bob: I was at the appointed place on time. When you struck the match to light your cigar I saw it was the face of the man wanted in Chicago. Somehow I couldn't do it myself, so I went around and got a plainclothesman to do the job.
Some readers may consider Jimmy's betrayal of his old friend reprehensible, but it could be countered that the friendship ended the moment Bob lit his cigar and revealed he was a wanted criminal who probably had a long record. Jimmy must have been shocked when he saw that face in the matchlight. He displayed another admirable character trait by maintaining the same facial expression and tone of voice. Jimmy acquired a lot of experience in his years as a policeman. Those old-time beat cops were admirable figures. They were expected to make their own judgments as rulers of their little microcosms within the great macrocosm of the big city. O. Henry opens the story by describing Jimmy's twirling his club.
Trying doors as he went, twirling his club with many intricate and artful movements, turning now and then to cast his watchful eye down the pacific thoroughfare, the officer, with his stalwart form and slight swagger, made a fine picture of a guardian of the peace.
That club was a symbol of the cop's authority. He had to make many decisions every day in enforcing the law. He made them on the spot, as a rule, without consulting his superiors. He was, as O. Henry says, "a fine picture of a guardian of the peace." Jimmy may have been a beat cop for nearly twenty years. He would have acquired a tremendous amount of practical wisdom in that time.
Bob, on the other hand, would have acquired his own store of wisdom, but it was largely crooked wisdom. He knew how to manipulate people for his own advantage. He tried to manipulate the man he took to be a uniformed cop.