He is remembered for his polite demeanour, good looks, and his ability to enliven social gatherings with conversation and music, which likely played a significant role in his diplomatic success.
[1] "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" - wrote a contemporary of Troilo.
His instructions were to reaffirm the shared interests stemming from the dynastic ties formed by the marriage of Prince Francesco de' Medici to Joanna of Austria.
[7] In October of the same year, he returned to France for the wedding of the King Charles IX to Elizabeth of Austria, with the task of conveying Pope Pius V's intention to confer the title of Grand Duke upon Cosimo de' Medici.
Orsini left Poland shortly after Henry, who had been summoned to assume the French throne following Charles IX's demise and had relinquished the Polish crown.
Upon leaving Krakow, he reunited with the king in Venice and together with the Medici envoy Sigismondo de Rossi, he represented the Grand Duke at the Venetian festivities in Henry's honour.
In a letter addressed to Antonio Serguidi, secretary of Grand Duke Francesco, Tremazzi confessed to receiving the assignment to assassinate Orsini from Count Ridolfo Isolani and Don Pietro de' Medici, the youngest son of Cosimo I. Tremazzi painstakingly reconstructed the steps taken to approach Troilo, whose access proved challenging due to Troilo's role as a gentleman of the chamber to Henry III, spending significant time at the royal court.
According to the contemporary account of the nuncio in Paris, Antonio Maria Salviati, Orsini was aware of his assailant's identity but chose not to reveal it, even on his deathbed, and forgave the individual.
During a period of political tension with Tuscany, Queen Catherine disapproved of the systematic elimination of Florentine exiles in France, as it jeopardised the king's sovereignty.
These missives confirm the existence of an illicit liaison with a married woman of esteemed Florentine lineage who ardently professed her affection for him ("from the first day that I spoke to him I was so excited about him that I have never lived quietly, and your lordship be sure that I love him and adore him as much as possible").
[18] Murphy, in her research, presents a compelling array of evidence connecting these letters to a married woman of the highest echelons of the Medici court, who could only have been Isabella (her sisters having already passed away).
She posits that naturally, given the perils involved, Isabella would have taken extraordinary measures to conceal her true identity, which would have included refraining from signing her name or employing her own handwriting.
[20] [21] In the eighteenth century, Riguccio Galluzzi reported on Isabella's death, stating that it was his opinion that her husband strangled her out of jealousy of Troilo Orsini,[22] her relative, who was assassinated in France not long after her.
In ambassadorial dispatches by Ferrarese ambassador Ercole Cortile there are also claims of a third child born to Isabella in May 1576 in the Medici villa of Caffagiolo, whose father could not have been her husband due to his absence.