Carlo I Malatesta

[1] Francesco I Gonzaga married Carlo's sister Margherita Malatesta in 1393, cementing ties between the families.

Carlo I Malatesta was one of the most respected condottieri of the time; he enlarged the Riminese possessions and restored the port.

In 1394, he was placed in charge of Rocca Contrada, a town important in the local balance of power, located at the border of the Marca di Ancona, Umbria, and the Duchy of Urbino.

He then negotiated a settlement with Francesco Gonzaga as representative of the Duchess of Milan, by which Bologna, Perugia, and Assisi were returned to the papacy.

Pope Boniface IX, not wishing to prolong an expensive conflict, later accepted the terms, despite opposition from both Florence and Bologna.

In the chaotic situation created by the presence of three popes at the same time, he backed Gregory XII, whom he also housed at Rimini, until his abdication at the Council of Constance.

Guillaume Du Fay's ballade "Resvellies Vous" (Awake and be merry) was written for the marriage of this younger Carlo in 1423.