HISTORICAL CONTEXT AND THE ORIGINS OF MILITARY POWER

Medieval and Renaissance Romagna was a borderland where Papal authority clashed with the seigniorial particularism prevalent in many of the region’s centers: examples include Ravenna with the da Polenta family, Faenza with the Manfredi, Imola with the Alidosi, Rimini with the Malatesta, and finally, Forlì with the Ordelaffi. The sovereignty of this latter house over Forlì proved to be a significant experiment in autonomous governance, initially characterized by a struggle for survival against the Papal States and a strong bond with the Ghibelline faction. The rise of the Ordelaffi as a regional power was the result of a gradual erosion of communal institutions, accelerated by the need for military leadership during a period of chaos. The Ordelaffi dominated Forlì and parts of Romagna—with periods of interruption and reconquest of the Lordship—from the late 13th century to the end of the 15th century.

Like the Baglioni of Perugia or the Gonzaga of Mantua, the Ordelaffi embodied the Italian warrior-lord. Their hegemony was never simply acquired; it was conquered daily with weapons and defended from within using poison or the dagger. Their history is interwoven with strategic alliances—the Empire, the Visconti, Venice—and internal feuds that often took on tragic tones.

In a Romagna torn by the struggle between Guelfs and Ghibellines, the Ordelaffi distinguished themselves as entrepreneurs of war. Their members were rulers and condottieri (mercenary captains), whose military campaigns funded city fortifications like the Rocca di Ravaldino. The price was high: the family genealogy is marked by fratricidal violence, an endemic virus that infected every generation until the disappearance of the house.

The rise of the Ordelaffi must be understood through the lens of the permanent state of war existing in Italy at the time. They transformed Forlì into a Ghibelline bastion, challenging Popes and Legates with a ferocity that bordered on heresy. From Scarpetta to Francesco “the Great,” from Pino III to Antonio Maria, their history is that of a dynasty that preferred to burn in the fire of war rather than fade away in obedience.

THE PROTAGONISTS

SCARPETTA ORDELAFFI

c. 1260 – 1315. Brother of Francesco I/Cecco I and Sinibaldo I. Lord of Forlì from 1295 to 1315. Dino Compagni defines him in his Cronica as a “gentle and temperate man.” He succeeded Maghinardo da Susinana both in the lordship of the city and as a reference point for the Ghibelline forces of Romagna and Tuscany. Scarpetta emerged as the founder of his house’s military power and a man skilled in weaving alliances beyond the city walls. Appointed Captain General of the Romagnol Ghibellines, alongside Uguccione della Faggiuola and the Lord of Urbino, Federico da Montefeltro, he led numerous campaigns against the Florentines, Angevins, and Romagnol Guelfs. After his capture by adversaries and subsequent release from the prison of Castrocaro (where Fulceri da Calboli was Lord), his role in Forlì became marginal. Officially, he remained Lord, but the government was effectively run by his brother Cecco I, who assumed the direction of the family and the city, seemingly content with only the title of Captain of the People. Scarpetta Ordelaffi remains in history for having given asylum to Dante Alighieri.

PINO I ORDELAFFI

Lord of Bertinoro from 1306 to 1310.

FRANCESCO I / CECCO I ORDELAFFI

d. August 1331. Brother of Scarpetta and Sinibaldo I. Lord of Forlì from 1315 to 1331. After succeeding his brother, he quickly displayed centralizing tendencies. He rid himself of local Guelfs, abolished the ancient constitutions, and entrusted all public offices to Ghibellines of proven loyalty. This evolution provoked a reaction from the Romagnol Guelfs who, led by the Orgogliosi family and aided by the Manfredi of Faenza, attempted in vain to enter Forlì. A similar operation was repeated a few years later with the same outcome. Finally, struggles resumed with the Guelfs, now aided by Papal forces. In July 1331, he was assaulted in Forlì. During the siege operations, he was dragged by his horse and fell to the ground. Bedridden and prostrated by the loss of strength, he died after a few days. He was succeeded by his nephew Francesco II, son of his brother Sinibaldo I, who can be considered the true founder of the family’s power. The political chaos of the early 14th century was, in fact, the soil in which the Signorie were born, with the Papacy and large states like the Duchy of Milan, or the republics of Florence and Venice, reshuffling the deck from time to time.

SINIBALDO I ORDELAFFI

Brother of Scarpetta and Francesco I/Cecco I. Father of Francesco II. A Ghibelline, he married a Guelf, Onestina da Calboli, sister of Fulceri.

FRANCESCO II ORDELAFFI

c. 1310 – October 1373. Son of Sinibaldo I. Husband of Cia degli Ubaldini (a legendary woman warrior figure), father of Ludovico I, Sinibaldo II, Teodorico, and Tebaldo I. Nephew of Fulceri da Calboli, son-in-law of Giovanni degli Ubaldini. He held the Lordship of Forlì from 1331 to 1359. He is the most powerful figure of his house and one of the most famous characters of 14th-century Romagna. He is the prime example of how one could violate the rights of the Papal States. A valorous commander, he was bold, impulsive, and obstinate in his actions. Guelf sources define him as a perfidious tyrant, without faith and without mercy. Others describe him as beloved by the population. Endowed with a personality that saw him as both cruel and extraordinary, for decades he fought both the Papal forces wishing to seize Forlì and its territory, and neighbors like the Malatesta, with whom discord was never-ending. Excommunicated multiple times, Cardinal Egidio Albornoz preached a crusade against him, offering special indulgences and the forgiveness of sins of all kinds (for a fee) to anyone ready to face him. Francesco II—the heretic, the Antichrist, the demon—was not fighting a personal battle against Catholicism, but against the ecclesiastical hierarchies, from simple priests up to the Vicar of Christ on earth. His end closed an era, an epoch in which lords and commanders loved to flaunt their allegiance to a faction, be it Ghibelline or Guelf.

LUDOVICO I ORDELAFFI

Son of Francesco II, brother of Sinibaldo II, Teodorico, and Tebaldo I. He fought the Papal forces alongside his father.

SINIBALDO II ORDELAFFI

1336 – October 1386. Son of Francesco II. Married to Paola Bianca Malatesta, daughter of the Lord of Fano, Pandolfo Malatesta. Lord of Forlì from 1376 until his death. A Lord very much loved by the populace. He was a cheerful man who made promises easily but did not always keep them; very proud, quite devout; he knew how to value his collaborators. His death was tragic. He received a famous astrologer at court who, reading his astral conjunctions, revealed the existence of a conspiracy against him involving his nephews Pino II and Cecco II. They denied everything and were believed by him. Days later, Sinibaldo took part in a banquet; during the night, his nephews forced the door of his palace, demanded the tokens of the city fortresses, and locked their uncle in the Rocca di Ravaldino. A victim of the hasty ambition of the new generations, he was killed, probably by poisoning, after almost a year of imprisonment in that same castle.

GIOVANNI ORDELAFFI

1349 – 1399. Son of Ludovico I, brother of Tebaldo I. Married to Taddea Malatesta. He represents the Ordelaffi forced to become a soldier of fortune; an Ordelaffi who, despite numerous attempts, failed to seize the Lordship of Forlì from his nephews Cecco II and Pino II. A captain of great valor, he was nicknamed “Giovanni Senza Paura” (John the Fearless). He embodied the typical condottiero of his time. He is described as an imposing man, very fat, with a sparse beard, and one of the best swordsmen of his era, as recorded in the Flos Duellatorum (or Fior di Battaglia), a sort of Bible for duelists in 15th-century Italy. Affable and generous with his men, arrogant and greedy with other captains with whom he found himself serving in the same enterprise. In his long career, he fought for the Este, the Sienese, the Malatesta, the Angevins of Naples, the Perugians, and the Bolognese. Always at odds with his nephews. Finally recalled to Forlì by Pino II, he was poisoned by a courtier at the instigation of that same relative.

PINO II ORDELAFFI

c. 1356 – July 1402. Brother of Cecco II. Son of Teodorico. Married Venanzia Brancaleoni, Venanzia da Varano, and Costanza Pio. With his brother, he killed his uncle Sinibaldo and his cousin Giovanni. Lord of Forlì from 1386 to 1402. He is described as a man of large build, with a rubicund, sanguine face, cheerful and handsome. He died of an apoplectic stroke.

CECCO II ORDELAFFI

d. September 1405. Brother of Pino II. Son of Teodorico. Married Caterina Gonzaga of the Novellara branch. Father of Lucrezia (wife of the Lord of Cesena, Andrea Malatesta) and Antonio (natural son). He exercised the Lordship of Forlì from his brother’s death until September 1405. Described by sources as a tall and thin man, good-looking, irascible, and a lover of fine wine. Of the two brothers, he was the elder, with little experience in government, dedicated more to arms and hunting than to statecraft. His rule, according to some commentators on Romagnol history, was essentially useless and dangerous for the continued presence of the Ordelaffi in Forlì.

TEBALDO I ORDELAFFI

1353 – 1382. Son of Francesco II; brother of Sinibaldo II, Ludovico I, and Teodorico. Father of Giorgio.

GIORGIO ORDELAFFI

d. January 1423. Natural son of Tebaldo I; father of Tebaldo II and Antonio. Married Lucrezia Alidosi. Lord of Forlì from 1411 to January 1423. He was nominally succeeded by his son Tebaldo II (1413–1425). The lack of an adult heir offered the Duke of Milan, Filippo Maria Visconti, the opportunity to conquer part of Romagna, including Forlì. He was the first to settle in the new Palazzo della Signoria, where he hosted Pope Martin V. His lordship was rather colorless: the chronicles of the time report no particular actions worth remembering, except on rare occasions.

ANTONIO ORDELAFFI

c. 1388 – August 1448. Natural son of Giorgio. Father of Cecco III and Pino III. Married Caterina Rangoni. Returning to Forlì with the help of Visconti arms, he held the lordship between 1433 and 1436. After being expelled again by Papal forces, he returned to dominate the city—always with the help of the Duke of Milan, Filippo Maria Visconti—from 1438 until his death from the plague. Due to the young age of their children, his widow called upon her brother Ugo to assist in the regency of Forlì. In 1454, his sons Cecco III and Pino III, intolerant of their uncle’s guardianship, forced him to abandon the city. Sergio Spada, in his work regarding the Ordelaffi, describes his figure thus: “It is not easy to speak of the psychological profile, even before the political one, of Antonio Ordelaffi. Even Giovanni di Mastro Pedrino, although a direct spectator of all the events that saw Antonio as a protagonist, expressed feelings of sympathy, spite, affection, and annoyed astonishment toward the lord, as if he himself did not clearly have the traits to draw the face of a controversial man, different on every occasion from himself, ungraspable. Even politically, Antonio divided his years each time between acclaim and exile, between the love and the contempt of the people.”

The second half of the 15th century saw Forlì under Cecco III and Pino III. This period represents the lowest point from a moral perspective and, paradoxically, a moment of splendor for the house. Poison assumed an increasingly important role in regulating internal affairs.

CECCO III ORDELAFFI

March 1435 – April 1466. Brother of Pino III. Father of Antonio Maria and Ludovico II. Married Lucrezia Malatesta, daughter of the Lord of Rimini Sigismondo Pandolfo Malatesta, and Elisabetta Manfredi, daughter of the Lord of Faenza Astorre II. Lord of Forlì until his death. Unscrupulous and ambitious, he lived in eternal discord with his brother, toward whom he felt a certain jealousy because, in his view, his mother preferred the brother (who was sickly) while Cecco was physically imposing. He was thus suspected of attempting to poison his brother. This triggered hatred between the two Ordelaffi, fueled also by their mother Caterina Rangoni and uncle Ugo. In April 1466, he lay ill. His minister, Francesco Bifolci, had for some time been exercising power dishonestly. His brother’s supporters took advantage of the situation and instigated the population against Bifolci’s greed and theft. Pino III rode the wave of the city revolt; his supporters imprisoned his brother Cecco III along with his wife Elisabetta and their children. There was an attempted poisoning by his sister-in-law Barbara Manfredi, also a daughter of Astorre II. In the end, one of the conspirators burst into the prison and killed Cecco III with a stiletto blow to the heart.

PINO III ORDELAFFI

March 1436 – February 1480. Brother of Cecco III. Father of Antonio Maria and Ludovico II. Married Barbara Manfredi (daughter of the Lord of Faenza Astorre II), Zaffira Manfredi (daughter of the Lord of Imola Taddeo Manfredi), and Lucrezia della Mirandola. While his brother Cecco III was infirm, the government was exercised by his minister Francesco Bifolci, hated by the population for the taxes he imposed on the community. Pino’s rise to power in the city occurred through his brother’s murder. With the aid of his father-in-law Astorre II Manfredi, his soldiers seized the town square and main streets. He ordered the conspirators to go to Cecco III’s chamber and imprison him, his wife, and children in the Clock Tower. The minister was killed by the revolting crowd along with his son. A cord was tied to his genitals and the corpse was dragged to the Palazzo delle Gabelle to be hanged with trousers pulled down. The following morning there was a failed attempt to poison his relative. The situation was resolved by a nobleman who, accompanied by hitmen, burst into the prison holding the Lord of Forlì, who was killed with a stiletto blow to the heart. Becoming Lord of the city in 1466, he can be considered the last authentic personage of the house. His story is rich in glory and poison. He is, in fact, accused of various murders, ranging from fratricide (Cecco III) to matricide and uxoricide (Zaffira Manfredi). A ruthless calculator in private, he was capable of gestures of public devotion, such as when he had an altar erected in the church of San Francesco. He always proved attentive to the well-being of the people of Forlì, a munificent patron of the arts, and a shrewd administrator. He died in mid-February 1480 after a dinner at the home of his friend Francesco Paolucci. His wife Lucrezia della Mirandola is suspected of having poisoned her husband.

ANTONIO MARIA ORDELAFFI

May 1460 – February 1504. Brother of Ludovico II. Upon the killing of his father Pino III (note: context suggests this refers to the killing of his uncle Cecco III by his father Pino III, or the chaotic period following Pino’s death, though the text says “killing of his father Pino III by his brother Cecco III” which contradicts the previous section where Pino kills Cecco. Correction based on historical context: Antonio Maria was the son of Cecco III or Pino III depending on the branch, but the text says he is the son of Pino III. However, the text says “killing of his father Pino III by brother Cecco III”—this seems to be an error in the original Italian text, as Pino outlived Cecco. The translation reflects the source text, but be aware of this inconsistency.) he was imprisoned with his mother and brothers. He managed to escape first to Ferrara and then to Faenza to join Carlo Manfredi. The latter lost the lordship of the city to his brother Galeotto. Antonio Maria was forced to become a soldier of fortune and serve the Venetians. Only at the end of 1503 did he succeed in his goal of being recognized as Lord of Forlì. Ill for some time, he died in the first days of the following year. With his death, the main branch of the family was extinguished.

LUDOVICO II ORDELAFFI

d. May 1504. Son of Pino III and brother of Antonio Maria. Lord of Forlì from early February 1504 to early April of the same year. He died in Ravenna the following month, perhaps by poison. Thus closed a chapter with the exit of a great family from history.

Forlì, located on the Via Emilia, proved to be a strategic crossroads. The Ordelaffi transformed this position into a political asset, operating as a military enterprise. Every male member was trained for command and placed in the market of condotte (mercenary contracts). The proceeds from contracts with Venice, Milan, or Florence were reinvested in internal consensus and the upgrading of defenses. The Rocca di Ravaldino became one of the most impregnable fortresses in Italy. Unlike the Montefeltro family, the Ordelaffi practiced extreme political realism. Fanatical Ghibellines under Francesco, yet ready to negotiate with the Pope when convenient, they allied with Venice to balance Milan and vice versa. This fluidity, as for the Gonzaga, was the only way for a small lordship to survive among giants. The systematic use of spectacular violence was not madness, but a political message. The flaying of priests or the display of corpses served to paralyze internal opposition. The Ordelaffi understood that being feared was safer than being loved. Their trajectory ended with the dawn of the sixteenth century, when the Italian Wars swept away the small autonomous lordships.