Why would a hobo smoke cigars? It never made any sense to me, that a traveling migrant worker, which is what most of them were, would smoke something so ill-suited to such a hard lifestyle, but that's how they are always depicted. Finally, I think I found an answer in Patricia A. Cooper's book, "Once a Cigar Maker: Men, Women, and Work Culture in American Cigar Factories, 1900 - 1919."
"The cigar maker," wrote one lifelong observer of the CMIU, "is a wanderer." The description was simple but accurate. ... Travel also acted as a sort of rite of passage. This was especially true of hoboing. Most traveling was not hoboing, but everyone was expected to try it at least once. "I don't know why we did," remarked Ograin, but you had to take a hobo trip. If you didn't hobo - why they used to say, 'all right. You're through with your apprenticeship. Now go out and learn the trade.'"
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