He was nicknamed "the inept" due to his lack of courage and, differently from most of the male members of the family, he did not prove skilled in the art of war.
In 1431 he was ousted from Pesaro together with his brother Carlo, due to his poor government, and took refuge in Venice.
In 1433 he hired Federico III da Montefeltro to defend Pesaro and Fossombrone against his cousin Sigismondo Pandolfo from Rimini.
Although he was able to keep his territories, and overwhelmed by the debts made to hire other condottieri, in 1444 he sold Pesaro to Alessandro Sforza in exchange of 20,000 florins.
In 1448 he made peace with his cousins, Sigismondo Pandolfo and Domenico Malatesta, who pushed him to attack Pesaro.