Though it would not be a chronological "sequel," I think perhaps the most interesting way to continue the story would be to look back at where the two men diverged. Clearly Jimmy has remained true in the sense that he did not leave his home and he now walks the beat to protect the people of his city. He is even willing to take a chance on missing a collar because he feels a loyalty to his old friend even though he knows he is now wanted.
Tracking where the two men split up and perhaps even a short story that gives each man an opportunity to take the right path or the wrong one would be interesting. Particularly because O. Henry leaves so much out of the story, there is plenty of room for a prequel or sequel to examine the nature of the two men and what might have been the characteristic that led to their differing choices.
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