Serving the Borgia
Cesare tasked his three generals with conquering Romagna, but after they had done so, he placed the blame upon them in order to keep the confidence of the people. He had Ramiro executed as a "gift" for the citizens, but Oliverotto and Vitellozzo rebelled against Cesare after this, and took some of his land as their own.
Later, Cesare presented them with an offer that all would be forgiven if they only returned to him. They obliged, and re-entered his service.
- Oliverotto: "I never wished you any harm, Cesare. It was entirely Vitellozzo's plan!"
- Cesare: "Ha! Your sacrifice will prove invaluable to me."
- ―Oliverotto pleading to Cesare moments before his murder.
Months later, Cesare threw a "dinner" in Vitellozzo and Oliverotto's honor. However, when they arrived, Cesare spoke out to them, thanking them for handing Romagna to him, but claiming it was time to "shed his bloody gloves." As several Papal Guards arrived at Cesare's side, the two generals realized that it was an ambush, and charged into the fray with weapons drawn.
Though they were outnumbered, both Oliverotto and Vitellozzo overpowered the guards and advanced on Cesare. The Captain General watched them approach, and as the last surviving Papal Guard wounded Vitellozzo, Cesare armed himself with a crossbow and fired a bolt into Oliverotto's shoulder.
Some time later, both Vitellozzo and Oliverotto regained consciousness, and found themselves chained back-to-back. In front of them stood Cesare, alongside Micheletto Corella. Though Oliverotto attempted to blame Vitellozzo, claiming that the rebellion was all his plan, Cesare ultimately ordered Micheletto to strangle both Vitellozzo and Oliverotto, claiming that their "sacrifice" was invaluable to him.
- Oliverotto wielded a pistol and a sword in conjunction during the ambush at their supposed dinner. This style is most often used by the Papal guards.