In the short story “After Twenty Years” by O. Henry, we are told that the characters of Jimmy and Bob were, as young men, great friends. They were so close that, as young Bob left New York City to head west and make his fortune, the friends hatched a plan to meet again at the same restaurant after twenty years with the absolute confidence that they both would. And indeed, they both did. So, we see that both the friends were equally loyal and faithful to their friendship.

In spite of this similarity in the two characters, they are different as grown-up men when they met after twenty years. Jimmy Wales has gained importance and power as a policeman in the city and is a very dutiful officer. Though there was a soft spot in his heart for his old pal Bob, he remained true to his duty by sending another man to arrest him.

Again, Jimmy has been a lifelong resident of New York. We can see his love for the native town New York in the fact that he did not agree to leave the own at any cost, not even when his closest friend Bob pleaded him to do so to try their luck and find opportunities at the West. Jimmy remained in New York when his friend left the town.

Taking a closer look at the character of Jimmy, we can also find that he is rather rigid about his principles. Any other man would probably be more flexible when it comes to taking big decisions in life. In the story, we are told that it was almost impossible to take Jimmy out of New York:

You couldn’t have dragged Jimmy out of New York; he thought it was the only place on earth.

Moreover, he could have revealed his identity before Bob and tried to bring him in the right course of life by showing him a way to correct himself. But Jimmy seemed to be strict about everything and rather chose to arrest his Bob right-away, though it was with the help of another man.

Now, to look at the other character, Bob, he was similarly true to his friendship as Jimmy was. It’s hard to find people who would come a long way just to keep his promise to meet his old friend, that too, made twenty years before. Moreover, his faith in Jimmy speaks of ultimate trust:

“If Jimmy is alive on earth he’ll be here by that time. So long, officer.”

Unlike Jimmy, this man was very ambitious and chose to take the wrong path in the pursuit of making quick fortune. While Jimmy was too conservation and rigid about going beyond his comfort zone, Bob never cared to alter his ways to make his wish fulfilled, even if it was unlawful.

Bob’s love for luxuries was apparent in his clothing and the accessories he used. His scarfpin was a large diamond, oddly set. Moreover, the lids of his handsome watch were set with small diamonds.

When Bob was waiting for his friend, he had a conversation with the patrolling policeman there. And it revealed his egoistic and boastful nature.

“Did pretty well out West, didn’t you?” asked the policeman.

“You bet! I hope Jimmy has done half as well. He was a kind of plodder, though, good fellow as he was…”

In the above conversation, we see that though Bob was a criminal, he was confidently boasting about his success in the West. It was in his nature that he liked to talk big, even if there was no touch of truth or actuality in it.

Bob’s flight to the West in search of quick success, his indulgence in the unlawful activities and his boasting – all shows his lack of wisdom. But still, this character remains likable to the readers by his faithfulness to his friendship and his confident nature.