There was no question that Paolo Giordano Orsini was the most privileged member of his vast clan. Although he was unable to live within it, he had a guaranteed income from the vast estates that he controlled. He received pensions and benefits from individuals such as the king of Spain, without actually having to do anything, as Isabella had pointed out to him. And although Paolo claimed he was anxious for military service, ‘he has seen very little action’, as the Venetian ambassador remarked. The same ambassador concluded his summary of the Orsini lord with observations on his other chief characteristic – his profuse spending.
Life was not so easy for the majority of his Orsini relations. None had an estate anything like the size of the one Paolo Giordano ruled, and all needed supplementary income. A few entered the church, but the majority, if they wanted to make money as soldiers, had to actually go to war and fight. They were dependent upon the goodwill of courtiers and ambassadors who could advance their case and who were willing to promote them. Every quality such men possessed – guts, aggression, determination, wit, charm – was a marketable asset, and some possessed more of them than others.
No Orsini of his generation was more determined to succeed on his own merits than Troilo Orsini, who was the same age as his cousin Paolo. His line, the Monterotondo, named for the feud they held twenty kilometres north-west of Rome, was the one to which Lorenzo the Magnificent’s wife Clarice Orsini had belonged. She was Isabella’s great-great-grandmother, which made Isabella and Troilo distant cousins as well.
One of the first things that many noticed about Troilo was his good looks. If Paolo’s prodigious size was remarkable enough to be commented upon by his contemporaries, than Troilo’s ‘great beauty’ also drew the attention of ambassadors. ‘He was a man who was elegant in all his endeavours, extremely handsome, a great entertainer, a true courtier, the friend of all the ladies and gentlemen’ was a contemporary summary of Troilo.1 Although produced in the seventeenth century, some time after his death, a painting made at the French court by Anastagio Fontebuoni, depicting Troilo meeting Catherine de’ Medici, gives some indication of how those in Troilo’s world saw him. The courtly Troilo doffs his feathered hat and makes a deep bow to the French queen mother. His dark hair is curly and lustrous, his pointed beard neat and trim, his features refined, elegant and sensitive. He appears every inch the perfect cavaliere, cavalier, as any higher ranking soldier of his time was known. In this picture, even the famously unyielding Catherine de’ Medici seems rather taken with him.
Moreover, the young Troilo had not got by on his looks alone. By 1559, he was trying to raise money to establish his own company to take to France to fight in the Wars of Religion, and he took part in several military campaigns over the next few years. It seemed evident to many that, of his generation of Orsini, as a warrior it was Troilo in whom the spirit of his ancestors lived on. The Venetian ambassador’s assessment of him contrasts greatly with the one he gave of Paolo Giordano, describing Troilo as a young man ‘who has seen a great deal of war in France, and of whom there are great expectations …’2 The picture of Troilo as the able but merry cavalier is completed by the fact that, in addition to his horse and dog, he carried a violin with him on his campaigns, thus able to ensure all could enjoy singing and dancing in the evenings in the battle camps.
Still, Troilo’s handsome face, apparent charm and abilities as a soldier had not earned him a worry-free existence. Like many Roman noble families, the Orsini of Monterotondo had never really recovered from the toll of the 1527 Sack of Rome and were struggling financially. Troilo’s father was dead and so, as the eldest son, albeit unmarried, Troilo was responsible for his younger brother Mario and his married sister Emilia, who had financial problems of her own. He was not the head of his branch of the Orsini clan; that was his uncle, Giordano, who expected some parts of Troilo’s earnings to go towards the upkeep of the crumbling estate. However, in periods of ceasefire and peace, there were no military assignments to be had and no money to be earned. It was during such a period that Troilo inserted himself in Florence into Paolo Giordano’s retinue of extended family and hangers-on who lived in the Palazzo Antinori. In this way, Troilo would to some degree be able to live at the expense of his Orsini cousin, while also keeping a foot in the Medici camp and being open to any potential offerings that might be had from Cosimo. To a certain extent he worked for Paolo, obeying instructions from his cousin such as: ‘Because you know the issues more clearly than I do, I am desirous that you attend to the Pignatello [another Orsini fiefdom] negotiation as soon as possible. I am sending Maestro Bartucci, who will let you know fully what my wishes are.’3
At the other end of the spectrum, Troilo’s relations back at Monterotondo expected him to provide them with reports of Paolo’s activities, for anything that happened to Paolo Giordano, as head of their entire clan, had some impact upon their own lives. ‘I am happy to hear’, his uncle Giordano wrote to Troilo at the end of 1563, ‘that the financial affairs of Signor Paolo Giordano have improved … any honour and glory that comes to him, his relatives, servants and friends can participate in also.’4 Equally, anything shameful also reflected badly upon Paolo’s family. ‘Now it would be sufficient if he were only to have children,’ mused Giordano to Troilo.5
All the Orsini were anxious that Paolo have an heir in order to cement the relationship between themselves and the Medici. The following summer, Giordano wrote anxiously to Troilo: ‘I beg you to let me know if the pregnancy of the Lady Isabella is for real, and how long along she is, and if it is certain, I ask you to take the opportunity to advise the illustrious Lord Paolo that it please him to ensure that he governs his wife, so that the pregnancy does not fail as it did the other time …’6 This comment was a reference to the widely held belief that it was Isabella’s wild ways, her parties and her hunting that had caused her miscarriages in the past. It also gave a clear indication that the Orsini family felt that Paolo had no control over his wife.
Interestingly enough, in regard to this supposed pregnancy, Ridolfo Conegrano would tell the Duke of Ferrara: ‘Everybody says that the Lady Isabella is pregnant again, but she says it is not true.’7 The Ferrarese duke might well wonder why this Medici princess would be so keen to deny the truth in such a rumour, when most noblewomen were only too anxious to proclaim their fecundity the moment they thought they might be pregnant.
The only concern Troilo was supposed to have for Isabella lay in her position as his cousin’s wife, an instrument whereby his family at large could prosper. He might dance or sing with her, but if Troilo was playing by the rules, Isabella should be intoccabile, untouchable. She was Orsini property not to be sullied by his hands. But Isabella did not see herself in this way, and Troilo was personally ambitious. He could see that to prosper at the Medici court did not entail securing the favour of Paolo Giordano; one needed Isabella’s. And Troilo very badly wanted, indeed needed, to prosper. Moreover, like others in his family, he had little respect for Paolo; that his uncle freely told him to advise Paolo to govern his wife indicates they saw Paolo’s weaknesses quite clearly. Troilo would feel no compunction in exploiting them.
His interest in Isabella already ran deep in the months after her brother Giovanni’s death, suggested by the fact that, absent from Florence in the summer of 1563, a friend sent him a detailed report of her hunting accident, when she fell into a deep ditch. This news is the letter’s sole contents, and so was clearly the reason for the correspondence, his friend recognizing that Troilo would want to know what had happened to Isabella. That is not to say that Troilo saw Isabella only as a means of advancement. Her influence with her father aside, she was the ‘star of the Medici court’, the wittiest, most vivacious woman in Florence, an object of desire in her own right.
As for Isabella’s reaction to Troilo, it is not difficult to imagine why she would be attracted to him and why she would allow that attraction to go further. He was handsome and charismatic; moreover, he had lived the life of a soldier and had carried out brave military deeds. By contrast, while Paolo Giordano talked incessantly of wanting to go to war, he never actually went. For Isabella, Troilo seemed more like her war-hero grandfather, Giovanni delle Bande Nere, or one of those chivalric heroes from the tales of Ariosto, which had informed her world since birth, come to life. His persona came automatically imbued with romance. The fact he was her husband’s cousin – as well as her own – could only make an assignation with Troilo all the more pleasingly piquant for Isabella in its implicit danger.
As to how Isabella could facilitate such a relationship, she had everything she needed. She had her autonomy, and Paolo’s own family members recognized he did not rule his wife. Her father had created an environment in which he permitted sexual licence and, most importantly, he was not going to stand in the way of Isabella pursuing such activity. Her husband was frequently absent and she possessed her own properties, meaning it was not difficult for Troilo to come to her bedchamber at the Palazzo Medici or for her to invite him to the Baroncelli, where Isabella claimed she stayed ‘in her usual solitude’. There might have been any number of Signor Marios, Eliconas, charming pageboys and ambassadors with whom Isabella could dance, sing and flirt. However, they could not provide the kind of relationship with which she had grown up, somebody with whom she could connect on a deeper, more personal level. As such, Troilo Orsini was not simply Isabella’s lover; he became, as much as was possible, the replacement for the role her brother Giovanni had once fulfilled. That reason perhaps explains why Cosimo allowed his daughter this relationship, he being the only one who had the power to put a stop to it. Both father and daughter knew the marriage could not bring her satisfaction, and Troilo went some way to filling the lacuna in Isabella’s life that her brother had left and which her husband could not fill.