Juan Borgia, 2nd Duke of Gandia, was never really cut out to be a soldier. He was arrogant and self centred, and failed more than succeeding at anything. Yet Pope Alexander VI wanted one son in the church and another in the military, giving Cesare the Cardinal’s robes and Juan the armour. As we already know, Cesare wasn’t best pleased with this and would much rather have been the one out on the battle field. If he had been made a soldier from the outset then none of the failures that Juan instigated would likely never have happened. But of course it didn’t happen like that, and Juan Borgia was really a big failure and really quite unpopular. His arrogance made him unpopular with his troops and the butt of some rather nasty practical jokes – one such example being at the battle of Bracciano in October 1496.
Bracciano was, and is, a small town just to the north of Rome and in the 1490’s was held by the powerful Orsini family and the town itself was overlooked by a huge fortress. When Charles VIII had invaded Italy, him and his army stopped at Bracciano as they headed towards Rome. This of course really annoyed the Pope and lead to him excommunicating the Orsini family, which only made the long standing feud between Orsini and Borgia even worse. The long standing hatred between the two families meant that even though Alexander was Pope, the Orsini family could prove to be a huge threat to the Papacy. And so something had to be done. Not only had Alexander excommunicated them for helping the French in 1494, but in July of 1496 he had Virginio Orsini and his son thrown into the dungeons of Castel Dell’Uvo in Naples. Now, he would take their towns and their castles.
Pope Alexander chose Guidobaldo de Montefeltro, Duke of Urbino to command the expedition to take the Orsini lands. Juan Borgia was made second in command despite being completely inexperienced. It really was a tragedy waiting to happen. At any rate, on 26th October, Juan and Montefeltro entered St Peter’s basilica and Juan was given the title of Gonfalonier and Captain General of the Church. The next day, the two men left Rome at the head of their army to lay siege to the Orsini strongholds.
The campaign was a success to start with and they met little resistance. The strongholds of Sacrofano, Galeria, Campagnano and Anguillara were all taken without any trouble, and over 10 castles were taken in two months, but they knew when it came to Bracciano that things would be a bit more difficult. To make matters worse, flags flaunting the French colours were hung from the walls of the castle.
Bracciano castle itself was held by Bartolomea Orsini, Virginio’s sister and wife of Bartolomeo D’Alviano – a highly esteemed Orsini captain. Borgia and Montefeltro arrived in Bracciano in mid december and things started to go wrong from the outset. Montefeltro was wounded early in the siege, leaving Gandia to take control. Gandia of course had little success and the Orsini soldiers climbed the walls and shouted insults at Juan. They then played a particularly cruel joke on the young man, sending a donkey into the papal camp with a sign around his neck which read “I am the ambassador of the Duke of Gandia” and a rather rude note shoved up the poor donkey’s backside.