The Monaldeschi were one of the powerful noble families of Orvieto, central Italy, members of the Guelph party who contested with murders and violence the Ghibelline Filippeschi for control of the commune of Orvieto and the castelli of Umbria.
One branch especially, the Monaldeschi della Cervara, dominated the life and politics of Orvieto, resisting Papal power from the thirteenth to the fifteenth century
The central stronghold in the network of castelli that the Monaldeschi controlled was Torre Alfina, where tradition connected the central tower with Desiderius, the last king of the Lombards. Aside from a brief period 1314-16 when the Filippeschi seized it, Torre Alfina was the symbolic center of Montaldeschi power.
According to the family's history, the Monaldeschi had descended from Monaldo, a ninth-century Lombard feudatory of Charlemagne, whose three brothers were the progenitors of Florentine and Sienese nobles, the Cavalcanti, the Calvi and the Malevolti. The Monaldeschi appear in Orvieto documents from 1157. Their conflict with the Filippeschi surfaced in 1212. At Castiglione the fortress of the Monaldeschi was built in the fourteenth century with the rubble of the Castle of Paterno destroyed by Gerardo di Corrado Monaldeschi. The Monaldeschi towerhouse that rises above the rooftops of Civitella d'Agliano, overtopping the campanile of the church, still evokes the feudal power of the Monaldeschi at the limits of Umbria, on the banks of the Tiber; they were dislodged from Agliano by the Papacy in 1415, following the distracting Western Schism that had served to protract the Monaldeschi's medieval power.
The most famous of the family was Ermanno di Corrado of the Cervara branch, who between 1334 and his death in 1337 was the absolute Signore of Orvieto, where he suppressed civic liberties but demonstrated diplomatic and organizational finesse. At his death, however, the family's internecine quarrels broke the civic peace; the Monaldeschi ruptured along four lines each identified by their stemma or heraldic charge, the Monaldeschi della Cervara, Monaldeschi del Cane, Monaldeschi della Vipera and the Monaldeschi dell’Aquila. Angelo Monaldeschi della Vipera built the Castello della Sala on a rocky promontory about 18 km from Orvieto, not far from the border with Tuscany. His grandson, Gentile Monaldeschi della Sala, of the party of Francesco Sforza, made himself the Signor of Orvieto in 1437, in agreement with Pietro Ramponi, Ugolino da Montemarte, Ranuccio da Castel di Piero as well as others of the group called the Mercorini, who slaughtered the members of the opposing faction, the Muffati, who represented Papal power in Orvieto. More than sixty were killed and numerous houses were burnt. Gentile retained power for a decade, against the della Cervara branch. Later he fought the Venetian cardinal Pietro Barbo, who was to become Pope Paul II; in honourable defeat he was sent to Romania to lead the Pope's troops. Family contentions were calmed by the marriage in 1480 of Gentile's son, Pietro Antonio Monaldeschi della Vipera della Sala withhis cousin Giovanna Monaldeschi della Cervara.