Jimmy Wells is a police officer in New York City, a place he loves. According to Bob, Jimmy is "the truest, staunchest old chap in the world," suggesting he is both loyal and lives with integrity. Although Bob says Jimmy was a "plodder," that could mean that he is persistent and willing to work hard for long-term goals. Jimmy is impressive as a policeman; even the way he walks shows he is reliable and adept at his profession. Thus it is not surprising that he is able to instantly recognize Bob's face as matching the description of a criminal wanted by the Chicago police. Jimmy has a certain amount of sensitivity for his old friend's feelings; he doesn't have the heart to personally arrest him, so he sends a "plain-clothes man" to do the job. He writes a personal note to Bob to make sure he knows that he, Jimmy, was "at the appointed place on time."
Bob is two years younger than Jimmy. When he was 18, he went West to make his fortune. He says the West has given him "everything I asked it for," although he also says he has had to compete with "some of the sharpest wits" in order to get his share. This makes it sound as if he was somewhat ruthless, especially when he says that only the West can put "a razor-edge" on a man. He has obviously been "successful" in the West; he wears a diamond scarf pin and carries a diamond-studded watch. He is proud of himself, and the reader may wonder whether he was keeping the appointment with Jimmy more out of loyalty or out of a chance to show off to his old pal. Nevertheless, there is an indication that Bob does care enough about Jimmy to be ashamed at being revealed to be a criminal, for when he reads Jimmy's note, his hand trembles a little.
Clues to Jimmy that Bob is wanted by the Chicago police include his facial features--"a pale, square-jawed face with keen eyes and a little white scar near his right eyebrow." The diamond scarf pin and diamond-studded watch may have been additional clues. When Bob strikes a match to light his cigar, Jimmy is able to see his face and the scar clearly. The police bulletin may have also specified the height of the wanted man; Jimmy would have been able to guess his height by standing next to him.
Readers get their own clues that Bob may be a criminal, but they may not be obvious until readers look back after reaching the surprise ending. First, the way Bob jumps in to talk to the policeman so quickly, assuring him that "it's all straight" shows that he is nervous around officers. The diamond scarfpin and watch also are ostentatious and don't seem to fit with the scar-faced, cigar-smoking character. Bob says when he was in the West, he "kept hustling around over it pretty lively" and that he eventually got his "pile." A hustler is a petty criminal, and "pile" sounds like a greedy approach to life. Bob's mention of a "razor-edge" is another term that suggests a rough or violent life, as well as his statement that the West "has given me everything I asked it for." That could refer to robbery.
O. Henry strews plenty of clues throughout the story for Jimmy Wells and for the reader to figure out what kind of person Bob has become.
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