I'm no expert on Jesse James, but my guess is the song pretty accurately describes the way the outlaw saw himself. For all his brutality, Jesse James, like many criminals, presented himself as the poverty stricken victim of an unfair society. Therefore, robbing places where the rich kept money, like banks or trains, made him the unwelcome guest the song refers to.
All of this, of course, gives rise to a larger question. What is it about complete sociopaths that we find so fascinating? After all, Brad Pitt himself starred as Jesse James in a movie just a few years back. There must be something innate about us - our own darker natures, perhaps - which gives people like Jesse James their allure. Maybe it's only natural to find such people fascinating, then. When they start becoming influential, however...
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