In "After Twenty Years," the cop sees evidence that Bob is a wealthy man. For example, the cop notices a jeweled tie pin when he first sees Bob waiting in front of where a restaurant once stood. After Bob shares some details about being there to reunite with his old friend, Jimmy, he pulls out a jeweled watch providing more evidence of wealth. The cop even states to Bob, "You were successful in the West, weren't you?" Bob confirms that indeed he has been successful.
The cop is actually Jimmy, the man that Bob is there to see. It turns out that Bob has not achieved his wealth by honest means. He is wanted by police in Chicago. Jimmy does not wish to arrest his old friend, so he sends another man to do the job.
"Silky" Bob strikes the policeman Jimmy Wells as a very dapper, well-dressed man. As he stands there waiting in the doorway of "Big Joe" Brady's restaurant, everything about the guy just oozes money and class. He's wearing a large diamond for a scarf pin, and that must have cost him an absolute fortune. Using such a precious gem for something as simple as a scarf pin indicates that you have money to spare, and plenty of it.
After shooting the breeze with Jimmy for a short while, Bob pulls out a handsome watch, its lids set with small diamonds. Clearly, this is a man who likes his diamonds, and diamonds don't come cheap. As if we didn't already know, Bob has done pretty well for himself, as he confirms to Jimmy.
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