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In Forli conspirators killed Count Girolamo their ruler and captured his wife and small children. These conspirators knew they were not secure if they were not masters of the fortress, but the castellan was unwilling to surrender it. The prescribed behavior for widows was a popular topic for discussion in the early modern period. Various moralists, intellectuals and religious leaders published their ideas for proper conduct in general books of etiquette as well as in a number of treatises that specifically addressed widowhood. Caterina Sforza became a widow on 14 April 1488. Reared in the lavish court of Milan, one of the most important cultural centers in fifteenth-century Italy, Caterina was one of several illegitimate children of the powerful duke of Milan, Galeazzo Maria Sforza. From her careful manipulation of her performance in ritual, people know that Caterina was politically astute and recognized the power of self-presentation for the preservation of power.

Caterina Sforza (b. 1462/63–d. 1509) was the daughter of Galeazzo Maria Sforza (b. 1444–d. 1476), duke of Milan (r. 1467–1476), and his mistress Lucrezia Landriani (b. 1440/45–d. 1507). In 1477, she married Girolamo Riario (b. 1443–d. 1488), nephew of Pope Sixtus IV and ruler of Imola since 1473. He gained possession of Forlì in 1480. Sforza bore at least eight children with Riario, six of whom survived infancy, and she became regent for her son Ottaviano (b. 1479–d. 1533) when Riario was assassinated in 1488. She survived several conspiracies against her rule of Imola and Forlì in the 1490s, and she was deposed only when Cesare Borgia (b. 1475/76–d. 1507) invaded the Romagna region in late 1499. Taken prisoner in early 1500, she was released in July 1501. Sforza moved to Florence, where she plotted to retake the family territories. Neither she nor the Riario family ever resumed power and she died after a long illness in 1509. She was buried in the Murate convent, where she had maintained a cell for spiritual retreat. Sforza’s political cunning and forceful rule fascinated many in early modern Italy, including Niccolò Machiavelli, who came to Forlì in 1499 to negotiate her son Ottaviano’s military contract with Florence. In The Prince, Machiavelli highlights Sforza’s use of fortresses for protection. His version of her actions after Riario’s assassination in 1488 did much to promote her reputation as a sexually bold and merciless ruler. By all accounts, when Sforza entered the Rocca di Ravaldino to facilitate its surrender to the rebels, she instead mounted the ramparts with the intention to rule and challenged her enemies to kill her children, who were hostages. According to Machiavelli, in the Discourses, she then lifted her skirts to reveal her genitals, a gesture meant to emphasize her claim that she could bear more children, who would eventually avenge Riario’s murder. This purported act is an exaggeration of her actions, but this version of the events remains influential as part of her legend. Sforza has often been cast as an exceptional woman not only because of her long regency, but also because of her sexual independence during her widowhood and regency. Without a husband or father to patrol her sexuality, Sforza inspired many rumors about possible sexual partners. During her widowhood, she did indeed maintain relationships with at least two men, whom she claimed after their deaths to have married. Giacomo Feo (b. 1470–d. 1495) achieved much power in her court and was assassinated. They had a son, Carlo (b. 1490–d. 1550s). The second, Giovanni di Pierfrancesco de’ Medici (b. 1467–d. 1498), of the cadet branch of the Florentine family, did not gain political power and died of natural causes. During her final years in Florence, Sforza won custody of their son, Giovanni (b. 1498–d. 1526). She then oversaw his education and estates, and he grew up to became a famous military commander in Italy, known as Giovanni dalle Bande Nere, and father of the future duke of Florence, Cosimo I de’ Medici (b. 1519–d. 1574). Sforza’s Medici connections augmented her fame after her death.

Caterina Sforza (1462/3-1509) was famous during her lifetime because of her twelve-year regency over her husbands' territories in the Romagna region of Italy after his assassination. Scholars have focused on her political maneuverings and bold sexuality, but Sforza’s patronage and collecting were integral parts of her statecraft and merit further attention. Careful analysis of the surviving artifacts, combined with information culled from archival sources, reveals that Sforza, like her elite peers, was an astute patron and collector despite financial limitations. She updated fortresses and made key improvements to her subject cities, projects that demonstrated her beneficence as ruler. She also refurbished her residence to make it reflect the proper character of a prince and express humanist notions of magnificence and splendor. Always in need of more money, Sforza on occasion sought out workshops that championed cost-effective serial production and called on community support for some of the religious projects she initiated.