O. Henry's story "After Twenty Years" was published in 1906. Assuming that it was probably a contemporary story at the time, that would mean that Jimmy Webb and his friend would have parted ways around 1885. Although Bob doesn't say that he went to California, the term "West" definitely implies that as his ultimate destination. And if Bob wanted to make his fortune, California would have been a natural choice. Although the Gold Rush of 1849 was over, other booms were taking place in California, notably oil and real estate booms.
Railroads made it easy and cheap for people to make their way to the West Coast. In 1885 the Santa Fe Railroad entered southern California, and that set up a competition between railroads that led to ridiculously cheap fares. A person could travel all the way from the Midwest states to Los Angeles on a ticket that cost just $1. In 1887 alone, 120,000 people arrived in Los Angeles via the Southern Pacific Railway. A real estate boom was happening there at the same time; an acre lot that cost $100 in 1886 cost $1500 the following year. Between 1884 and 1888 about one hundred towns were planned in southern California. The first oil well had been dug in 1876.
Although Bob could have gotten his wealth legitimately in the West, he chose to run afoul of the law. Wherever there is a large influx of people and a booming economy, those who want to take advantage of others and pursue ill-gotten gain have a better chance of finding that kind of success, so California offered plenty of opportunity for the unprincipled "Silky Bob."
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