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I'm surprised this premise hasn't come up as much as it has, but what if the Spanish settlement known as San Miguel de Gualdape survived? Located somewhere near Georgetown in what is present day South Carolina (though this is up for debate), the settlement was an attempt by the explorer and sugar plantation owner Lucas Vázquez de Ayllón to tap into the unclaimed resources of North America, establishing a small village on the coast in 1526 with the help of 600 settlers and a number of African slaves. However, like so many other European attempts at North American settlement during this period, the small colony essentially fell apart over a very short period of time to disease, famine, infighting, troubles with the local Amerindians, and the first slave revolt in North American history, de Ayllón dying during the course of a particularly harsh winter, his successor Francis Gomez being forced to abandon settlement and take the remainding 150 survivors to Hispaniola.