The year that followed Piero’s and Maddalena’s high-ranking marriages in 1488 saw Piero faced with a choice between two different ways of life. On one hand, he had to play his part in the civic life of Florence and learn the political role that he would inherit from Lorenzo. On the other, he had been seduced by his reception in Rome and by the courtly pleasures he had experienced there with Franceschetto and his curial friends. Its impact on him became clear when, at the end of that year, he demanded two of Franceschetto’s men to accompany him to Milan for Gian Galeazzo Sforza’s wedding, ‘because here it’s impossible to find men who are their equal’.1 Like Hercules approaching the crossroads as a young man (according to the well-known tale told by Prodicus), he seemed to be faced by a choice between a rocky uphill path and an easy downhill one.2