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Skewball, born in 1741, was a racehorse bred by Francis, Second Earl of Goldolphin. The horse, a gelding, was purportedly the top earning racer in Ireland in 1752, when he was 11. The song apparently originated as a ballad about a high stakes race occurring in the Curragh in Kildare, Ireland in March, 1752, which Skewball won. The 1784 publishing date is for the oldest broadside identified of the ballad and is held by the Harding Collection of the Bodleian Library of the University of Oxford.

According to John and Alan Lomax in "American Ballads and Folk Songs", the ballad was converted into a work song by slaves -- which is supported by the version of the lyrics published in their book. "Skewball" apparently became "Stewball" after the song migrated to the United States.
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