Why does the police officer need to know if the man would wait for his friend or "call time on him sharp"?

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The policeman needs to know if the man will wait around because he has to make the decision whether to arrest him on the spot or to send another police officer in plainclothes to do it. The first policeman doesn't want to make the arrest because Bob—now the criminal Silky Bob—is his old friend. In fact, the policeman is the Jimmy Wells, from twenty years ago, whom Bob is waiting to meet.

Although Bob calls Jimmy a plodder and praises his own sharp wits, honed in the west, the irony is that Bob, who never left New York City, outwits Jimmy. If Jimmy had been sharper, he might have wondered about the question he was asked, and maybe he would have left right away after saying he would stay: but it doesn't occur to him (or the reader) to wonder why the policeman would make such a query.

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O. Henry wrote with irony, and the ironic aspect of this story is that the police officer is Bob’s old friend, the very man he is anxious to meet. When Bob lit up his cigar, the police officer, Jim, recognized him from a wanted poster as Silky Bob, a person wanted in Chicago. He knew he had to arrest him, but he couldn’t do it himself. His friendship was too strong. He had to get someone else to arrest him, so he went around the corner and contacted a plain clothes officer to handle the arrest. Jim needed to know that Bob would stay there waiting until he could contact the plain clothes officer. He didn’t want him to leave. He asked him how long he planned to wait for his friend. Would he leave at 10 sharp, or would he give his friend a few extra minutes. Bob replied,

“I’ll give him a half an hour at least.”  (pg 2)  

That was enough time for the police officer to contact the plain clothes officer and have Bob arrested.

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