15. Giuliano Dami and Gian Gastone
Gian Gastone, the last grand duke of the Medici dynasty, lived an outwardly fay lifestyle in one of the few places in Europe to condone homosexuality. Unlike many of his gay ancestors, he fathered no children. He did take on Giuliano Dami as a mentee and lackey. It’s believed that Dami was a frequent lover for the grand duke, but Dami’s loyalty didn’t inspire fidelity. Indeed, Dami often accompanied Gastone on trips abroad, but would end up serving as a pimp, finding younger men to participate in orgies with Gastone.