08. John of Gaunt

It's probably impossible to fully understand the events leading up to the Tudor dynasty without talking about perhaps the 14th century's most singular figure - at least from a historical perspective. John of Gaunt was the third son of King Edward III, and through beneficial marriages, became extremely rich in both land and money. His successes on the battlefield and the untimely death of his brother, Edward the Black Prince, made him a powerful political operator. But perhaps the most consequential thing John of Gaunt did was carry on a years-long extramarital affair with a woman named Katherine Swynford - resulting in four children who were given the surname "Beaufort." Theirs was a questionable lineage that would nevertheless have its day in the sun almost a century later.

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