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

Francesco Guicciardini, as we saw, famously attributed Italy’s ‘ruin’ after 1494 to Piero upsetting the balance of power between Milan and Naples by ‘throwing himself into the arms of Ferrante’ and ‘totally alienating Milan’. He was, of course, judging Piero in the light of what happened after the event, when Lodovico Sforza’s alliance with the king of France seemed to be a determining factor in the king’s victory and the overturning of the Medici regime. But before the French arrived in Italy, the situation was more fluid and Piero more concerned with preserving the balance held by his father than Guicciardini suggests. He was in fact wary of Ferrante and was in close contact with Lodovico, but since his diplomacy was often secret, like his father’s, hidden even from ambassadors like Piero Guicciardini in Milan, it is likely that Piero Guicciardini’s son, Francesco the historian, was unaware of it. Although the dispute over the lands had spoilt Piero’s visit to Rome, it only threatened Italy’s balance of power after the pope created the League of St. Mark to recover the lands from Virginio Orsini in April 1493. By following Piero’s moves in the face of this threat, we can understand better his secretive strategy to keep the old balance alive.1