Machiavelli supposedly wrote Il Principe for Lorenzo II de Medici, the duke of Urbino, on how to unite Italy. And the French certainly had plans for Lorenzo di Piero, namely using him as a cat’s paw for their gambit on Naples. They married him to Madeleine de la Tour d’Auvergne, a cousin of the French king, in the hopes that the duke and the duchess would make happy little half-French babies. Well, they made one – Caterina Romola de Medici – before they died. Now, Madeleine died first, but let’s assume Lorenzo pulls through (I think they died of the plague, but some sources posit smallpox or some other disease). What does the future hold for the duke of Urbino?