Although Bob and Jimmy used to be close friends back in the day, on the face of it, it doesn't seem like they have a whole lot in common anymore. "Silky" Bob, as he's known, has carved out a successful career as a criminal, which enables him to enjoy the trappings of wealth, such as fine clothes. Jimmy, on the other hand, has become one of New York's finest, dedicated to ridding the Big Apple of criminals like his former friend.
Another notable difference between the two men is that Bob, unlike Jimmy, is quite ambitious. A restless soul, he headed out West to seek his fortune, making his name as a career criminal. Jimmy, on the other hand, couldn't be dragged away from his home town, which is why Bob is certain that his old pal will turn up for their long-planned reunion at Big Joe Brady's in New York.
This leads us to one striking similarity between Jimmy and Bob: they both value their friendship enough to make good on that commitment they made some twenty years previously. Though their lives in the meantime may have taken radically different paths, they clearly still retain good memories of their younger days, when they were such good friends. And though one may be a career criminal and the other a cop, they both place a high value on friendship.
Although Bob and Jimmy were best friends as boys, as adults they became two very different types of men. They were both from New York City, and they were only two years apart in age, with Jimmy being two years older. As young men of eighteen and twenty, they hadn't yet decided upon their respective career paths. Both felt equally committed to their relationship and so agreed to meet in twenty years to compare notes. Each of them remains true to that promise and arrives at the appointed meeting place at the appointed time.
Even at the time they parted ways, they had some differences. Jimmy thought New York was the best place on earth and never wanted to leave it, while Bob was interested in going west and making his fortune. Twenty years later, they had diverged significantly in their way of life and values. Bob, now known as "Silky Bob," chose a life of crime, which led to his being wanted by the law in Chicago. He became wealthy by competing "with some of the sharpest wits going," but that means he probably tried to outsmart other criminals as well as deceive honest men in order to get his riches. Nevertheless, he is proud of his achievements.
Jimmy Wells, whom Bob describes as always having been a "plodder," became a law enforcement officer. Bob says he "always was the truest, staunchest old chap in the world." This proves to be a correct analysis of Jimmy's character. Jimmy did his best to remain true to their friendship, but he also valued truth and honesty, which meant he had to have his friend arrested. Jimmy seems humble; he doesn't lord it over Bob but sends another officer to take Bob into custody.
Both men are apparently intelligent and clever, but Jimmy proves to have the sharper wit in the end, which allows him to fulfill his "destiny" more successfully than Bob does, since Jimmy will continue his police work while Bob's days as a criminal are presumably over.
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