Oliverotto Euffreducci, known as Oliverotto of Fermo (1475, Fermo - 31 December 1502) was an Italian condottiero and ruler of Fermo during the pontificate of Alexander VI. His career is described in Niccolò Machiavelli's Il Principe.
 Early life and rise
Euffreducci was born in Fermo.
During his childhood, he was brought up by his uncle, Giovanni Fogliani after he was left fatherless. He was sent to serve as a soldier under the condottiero Paolo Vitelli in order to win high command. After Paolo's death, Oliverotto soldiered under his brother, Vitellozzo Vitelli, and became his commander. As his ambition grew, Oliverotto wanted to seize Fermo for himself. In 1495, he associated with Paolo Vitelli and fought with him first at Pisa and then in Naples for the French. A few years later, Oliverotto and Vitelli were fighting against the Venetians. In 1499, the two were fighting for the Florentines against Pisa, but both were accused of treason by Florence. Vitelli was summarily put to death while Oliverotto was spared due to the intervention of the government of Fermo. He then united with Vitellozzo Vitelli, Paolo's brother, and both went into the service of Cesare Borgia. Consequently, he wrote to his uncle, claiming he wanted to meet him. Suspecting no foul play from his nephew, Fogliani brought the citizens of Fermo and lodged him in his own mansion. Soon, Oliverotto prepared a formal banquet in which he invited the prominent people of Fermo and his uncle. As Machiavelli put it:
When the viands and all the other entertainments that are usual in such banquets were finished, Oliverotto artfully began certain grave discourses, speaking of the greatness of Pope Alexander and his son Cesare, and of their enterprises, to which discourse Giovanni and others answered; but he rose at once, saying that such matters ought to be discussed in a more private place, and he betook himself to a chamber, whither Giovanni and the rest of the citizens went in after him. No sooner were they seated than soldiers issued from secret places and slaughtered Giovanni and the rest.
Then, Oliverotto laid siege to the palace of the governing council, and, having scared them all, set up a government in the form of a dictatorship. Later, he made himself a formidable ruler to all of his neighboring states.
 Downfall and legacy
In May 1502, Oliverotto conquered Camerino for Cesare Borgia. However, realizing that the Duke was becoming stronger, he attended the meeting at La Magione with Paolo and Francesco Orsini, Rodolfo Baglioni, Pandolfo Petrucci, Vitelli and others, on 9 October. Although Oliverotto was against Paolo Orsini's line of reconciliation with Cesare Borgia, he nonetheless took Senigallia in Cesare's name. But this didn't change Borgia's secret design, and the Duke had him arrested and strangled, together with Vitellozzo Vitelli, on 31 December 1502. Oliverotto was succeeded as ruler by his son Ludovico, who ruled until he was killed at the Battle of Monto Giorgio in 1520, when Fermo became again directly subjected to the Holy See.
- The Prince, page 30, Stage VII; Niccolò Machiavelli; Published by Kessinger Publishing, LLC, 2004
- The Prince, page 31, Stage VII; Niccolò Machiavelli; Published by Kessinger Publishing, LLC, 2004
- The Prince, page 31; Niccolò Machiavelli; Published by Kessinger Publishing, LLC, 2004