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Stories about riverboat gambling and gamblers persist to this day. Why? In this episode, I talk with historian and author Thomas Ruys Smith about the pre-Civil War gambling scene on the Mississippi River. We peel off the patina of romanticism and go deep into the realities of gambling on the Mississippi River. We talk about the presence of gambling on the river before steamboats plied the Mississippi and how the destruction of the red-light district in Vicksburg reorganized gambling activities. We then go deeper into the world of riverboat gambling, touching on which games of chance were common, the background of gamblers, the role of the ship’s crew in supporting or tolerating gamblers, the consequences of getting caught cheating, some common myths about gamblers. We wrap up with a discussion about the eventual decline of riverboat gambling, how and when the image of riverboat gamblers got a makeover into mythic heroes, and the thread in American history of turning outlaws and rule breakers into heroes.