Paolo Orsini
During this time Paolo was the head of the Orsini's house. When the Orsini participated at the Diet of La Magione, which was directed against the Pope's son, i. e. Cesare Borgia, they knew very well that Pope Alexander VI had already determined to destroy them—and with them, the Colonnas as well. As soon as Cesare Borgia (the Duke Valentino) had become aware of the conspiracy against him, he tried very hard to work on Paolo Orsini and offered him a formal treaty of reconciliation, while the Valentino was biding his time. The treating was undersigned at Imola by both Cesare Borgia and Paolo Orsini on October 28, 1502. It was then taken to the conspirators, or "confederates", for discussion and ratification. Subsequently Orsini brought the signed pact back to Imola late in November. Cesare now moved to Cesena, some 60 miles Northwest of Sinigallia, and ordered the confederates to take this latter city which is located on the coast. Of course this was a trickery. Duke Valentino, as Machiavelli says, "was so skillful in disguising his intentions that the Orsini themselves sought to be reconciled with him through the mediation of Signor Paolo, whom the Duke tried to placate in every way conceivable, giving him money, fine clothes, and horses. Thus the simple-mindedness of the Orsini brought them to Sinigaglia, and into the duke's hands" (Machiavelli, The Prince, chapter 7). Three days after Christmas the Valentino sent most of his French reinforcement away, and requested the confederates to withdraw their men from Sinigallia. This trick, too, worked and the plotters were take prisoners, and some of the were strangled. Paolo was able to escape. However, he was caught after a few days and strangled with others at Città della Pieve on January 18.