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Frederigo da Montefeltro
Guidobaldo da Montefeltro
Francesco Maria della Rovere

Dukes of Urbino

by John Sloan


Burckhardt, Jacob, The Civilization of the Renaissance in Italy, 2 vols. Harper Torchbooks, New York, 1958.

Castiglione, Baldesar, The Book of the Courtier, trans by Charles Singleton, Anchor Press, New York, 1959

Contamine, Philippe, War in the Middle Ages, trans Michael Jones, Basil Blackwell, London, 1984.

Cronin, Vincent, The Florentine Renaissance, Dutton and Co., New York, 1967.

Cronin, Vincent, The Flowering of the Renaissance, Dutton and Co., New York, 1969.

Durant, Will, The Renaissance, Simon and Schuster, New York, 1953.

Gilmore, Myron, P. The World of Humanism, 1453-1517, Harper Torchbooks, New York, 1952.

Hale, John, The Civilization of Europe in the Renaissance, Atheneum, New York. 1994.

Lucas, Henry, The Renaissance and the Reformation, Harper and Row, New York, 1934.

Machiavelli, Niccolo, The Discourses on the First Ten Books of Titus Livy, ed by Leslie Walker, Routledge and Keegan Paul, London,

Machiavelli, Niccolo, The History of Florence, ed by Myron Gilmore, Twayne Publishers, New York, 1970.

Middleton, John Henry, "Raphael Sanzio", Encyclopedia Britannica, 11th Ed, Vol 22, pps. 900- 908.

Norwich, John Julius, ed. Great Architecture of the World, Random House, New York, 1975.

Oman, Sir Charles, A History of the Art of War in the Sixteenth Century, New York, E. P. Dutton, 1937.

Plumb, J. H. The Italian Renaissance, Harper Torchbooks, New York, 1959.

Plumb, J. H. ed. Renaissance Profiles, Harper Torchbooks, New York, 1958.

Smith, Denis Mack, article on Frederigo da Montefeltro in Plumb's Renaissance Profiles

Schevill, Ferdinand, Medieval and Renaissance Florence, 2 vols: The Coming of Humanism and the Age of the Medici, Harper Torchbooks, New York, 1958.

Tedder, Henry R. "Libraries" Encyclopedia Britannica, 11th ed. Vol. 16, pp. 545-577.

"Urbino:, Encyclopedia Britannica, 11th ed. Vol. 27, p. 792.


The three dukes of Urbino are certainly not obscure figures in the history of Renaissance Italy. The reader finds mention of one or the other of them in most recent histories of the period. But mention is about the extent of it. Beyond that it is difficult to develop a full picture of any of them. The first duke, Federigo, is written about the most. It is his portrait that is included in so many textbooks as an example either of a conditierri or of Renaissance portraiture. The following essay is prepared in an effort to bring together what information is available in the general works listed in the bibliography. In addition to the brief notices of the activities of one of the dukes the essay provides some background information on what was occurring around them. Unfortunately, from these sources it is not possible to draw a complete picture of events and especially of the duke's personal activities.


1422 - birth of Federigo (illegitimate), Oddantonio was his half brother, source does not mention father's name.

1422- 1432- boy held hostage in Venice and then sent to school in Mantua

1431-1447 - Papacy of Gabriele Condulmer as Eugene IV

1432 - Federigo knighted by Holy Roman emperor, Sigismund

1437 - Federigo returns from Mantua and is married to Gentile Brancaleoni, also begins military service.

1442 - Florence hires Count of Urbino (Federigo's father?) as commander for war against Lucca. He is defeated at Serchio River.

1443 - Oddantonio Montefeltro becomes ruler on the death of their father

1444 - assassination of Oddantonio, Federigo becomes Lord of Urbino

1445 - Federigo helps Sforza family win Pesaro.

1447-1455 - Papacy of Tommaso Parentuceli as Nicholas V

1448 - Federigo organizes army for Florence

1450 - Federigo begins construction of his lavish palace

1455-1458 - Papacy of Alonso Borgio as Calixtus III, (uncle of Alexander VI)

1457 - death of his wife, Gentile; no children- Federigo marries Battista Sforza, daughter of Alesandro,

1458-1464 - Papacy of Aeneas Silvio de Piccolomini as Pius II

1460 - Federigo assists Argonese dynasty to hold Naples

1461 - Federigo captures Aquila

1464-1471 - Papacy of Pietro Barbo as Paul II

1465 - Federigo appointed by Pope Paul II, commander (gonfaloniere) of papal armies

1467 - Federigo named commander of the league army against Venice. League included Florence, Naples and Milan, which sent sizable forces

1467 -Federigo with league troops wins Battle of Molinella against Bartolomeo Colleoni, commander of Venetian troops.

1468 - Federigo brings the renowned architect Luciano Laurana to complete the palace at Urbino.

1468 - Death of Sigismondo Malatesta, Pope tries to acquire Rimini causing Federigo to switch sides

1469 - Piero della Francesca paints portraits of Federigo and Battista, proving that the brush is mightier than the sword. They are in the Ufizi Gallery in Florence and appear in many books on the Renaissance.

1471-84 - Papacy of Francesco d'Albizzola della Rovere as Sixtus IV (uncle of Pope Julius II)

1472 Death of Battista Sforza Montefeltro, Federigo's second wife.

1472 - Federigo raises army for Florence at request of Lorenzo di' Medici against Volterra

1474 - Federigo received at Vatican by Pope Sixtus IV and given title of Duke. Sixtus drives Niccolo Vitelli out of Citta di Castello.

1478 - Pazzi conspiracy in Florence

1479 - Federigo campaigns against Florence for Sixtus IV, who is allied with King Ferrando of Naples. Florence appeals to France.

1482 - The Vitelli recover Citta di Castello. On 3 May Venice, supported by Pope Sixtus IV, declares war on Ferrara, which is supported by Florence, Naples, and Milan. Federigo is allied commander.

1482 - Roberto Malatesta wins victory for Sixtus over Neapolitan army of Alfonso, Duke of Calabria

1482 - Federigo dies, Sept. 10th of malaria from campaign at Ferarra while his arch- rival, Roberto Malatesta, dies same day from dysentery. Guidobaldo succeeds his father as Duke of Urbino.

1483 - Birth in Urbino of Raphael Sanzio, whose father was also a well known artist at court, where he introduced his son, Raphael to the finest examples of art.

1484-1492 - Papacy of Giovanni Battista Cibo as Innocent VIII

1484 - Francesco Gonzaga succeeds his father, Federico, as Marquis of Mantua

1488 Guidobaldo Montefeltro marries Elisabetta Gonzaga, daughter of Federigo, Marquis of Mantua, and Margaret of Bavaria, and sister-in-law of Isabella, later Marchioness of Mantua

1492-1503 - Papacy of Alexander VI, (Rodrigo Borgia) Spanish cardinal (obtained by bribery)

1494 - Invasion of Italy by French King Charles VIII

1495 - Many events involving French invasion army and greater cities in Tuscany and Lombardy, Urbino out of line of march

1495 - July 6, Battle of Fornovo, King Charles is confronted during his retreat from Naples by Guidobaldo's brother in law, Gian-Francesco Gonzaga, Marquis of Mantua. Antonio, leads the Italian center. Italians are defeated.

1495 - Alexander VI employs Guidobaldo to crush the Orsini and Bartolommeo d' Alviano in the Romagna and Papal states. Alexander appoints Giovanni Borgia, Duke of Gandia, as Gonfalonier of the Church. The Baglioni, della Rovere, and Vitelli families join against the pope.

1497 - Battle of Soriano on 26 Jan. Papal forces defeated and Guidobaldo taken prisoner. Naples sends Gonsalvo de Cordova and Prospero Colonna to help the pope.

1498 - Machiavelli becomes Secretary of the Signoria and Chancellor to the Ten of Liberty and Peace in Florence

1499 - Another French invasion of Italy, King Louis XII enters Milan and princes of northern Italy submit. Caesare Borgia's first campaign in Romagna with French help.

1500 - Caesare Borgia's second campaign with French troops, takes Pesaro and Rimini, surrounding territories of Urbino

1500 - Treaty of Granada whereby King Ferdinand of Spain and King Louis XII agree to partition the Kingdom of Naples, but they soon fall out over the boundary.

1502 - Pope Alexander VI persuades Guidobaldo for loan of his artillery, whereupon Caesare Borgia takes Urbino on 21 June and seizes the art and library treasures. Guidobaldo escapes to Mantua and then Venice.

1502 - People of Urbino drive out the Borgia troops and proclaim the return of Guidobaldo on October 18. He destroys city fortifications (an action much applauded by Machiavelli). Caesare through the Pope's diplomacy forces Guidobaldo to flee again on 8 Dec.

1502 - Death of Pope Alexander VI, disgrace and arrest of his son, Caesare Borgia.

1503 - Papacy of Francesco Todoeschini-Piccolomini as Pius III, for 26 days

1503-1513 - Papacy of Julius II (Giuliano della Rovere), a great warrior

1503 - Raphael paints a St. George and a St. Michael for Guidobaldo to represent his victory over the Borgias.

1504 - Guidobaldo, restored to Urbino, goes to Rome to be named commander of Papal armies by the new Pope, Julius II, and humiliate the fallen Caesare Borgia.

1506 - Guidobaldo assumes command of the papal troops of Pope Julius II for the campaign to regain the Romagna and to take Bologna, but Julius is actually in command throughout.

1506 - Guidobaldo invested as knight of the Order of the Garter by King Henry VII of England, Castiglione sent to receive it.

1507 - Time of action of Castiglione's "The Courtier" set at palace of Urbino, where he lived for 11 years.

1508 - Guidobaldo dies and passes rule to nephew, Francesco Maria della Rovere (also nephew of Pope Julius II) who rules Urbino, beginning of end of Urbino high court life.

1509 - Marriage of Francesco Maria della Rovere to Eleanora Gonzaga eldest daughter of Marquis Francesco Gonzaga of Mantua and Isabella d'Este. (She was also a niece of Duchess Elisabetta)

1510 - Pope Julius sends Francesco Maria della Rovere to attack Ferrara.

1511 - Francesco murders Francesco Alidosi, Cardinal Archbishop of Bologna, at Ravenna on 24 May.

1512 - Battle of Ravenna, Alfonzo d'Este's artillery plays a prominent role. Expulsion of French from Italy and subsequent restoration of Medici to Florence

1513-1521 - Papacy of Leo X (Giovanni, Cardinal d' Medici) de facto ruler of Florence since 1512)

1515 - King Francis I brings his French army back to Italy and wins at Marignano.

1516 - Pope Leo X declares Francesco deposed in favor of Leo's nephew, Lorenzo d' Medici, who thereby becomes Duke of Urbino and is created Gonfalonier of the Church. Francesco fights vigorously to defend the city but Papal troops take it.

1517 - Francesco gathers disbanded Spanish and French troops and recaptures Urbino. Event noticed by Machiavelli as extraordinary.

1519 - Lorenzo d'Medici dies, reportedly from the effects of the campaign at Urbino.

1521-1523 - Papacy of Hadrian Florensz as Adrian VI

1523-1534 - Papacy of Giulio d' Medici as Clement VII

1538 - Death of Francesco della Rovere


Urbino town is on eastern slopes of Apennines facing the Adriatic. It is south of Rimini and Bologna and east of Florence and Sienna. The soil is poor and the climate given to extremes. The city had about 40,000 residents. For three centuries it was ruled by the Montefeltro family as feudal vassals of the Holy Roman Emperor or the Pope. The area was only thirty or forty square miles. But in the rugged hills the warlike, mountain people preserved their relative independence. The city did not have a port on the Adriatic and was not on any major trade route. All the coastal plain was controlled from Rimini and Ancona.
Federigo consolidated several of the local fiefs and expanded the state to three times its former size. The state had over 400 villages with 150,000 inhabitants by then. The duchy reached beyond Gubbio to the south and nearly to San Marino in the north. Federigo managed to keep the taxes of his city low by using the money and plunder he collected as a condotierre general to beautify the city and operate his court. Even when not on campaign, during the winter, he obtained a sizable retainer fee from his employers. He granted an unusual amount of political power to the citizens. He kept careful watch over the economic condition of his subjects and stored grain in the city in case of poor harvests to avert possible price rises. The city was noted for the production of majolica.
Even at its greatest Urbino was still a small city and tiny state compared to Milan, Naples, Venice or Florence. Federigo's skill lay in playing one power off against another and maintaining himself as much as possible as a balance of power. He and his son were both involved ultimately in the continual efforts of one pope after the other to expand papal control over the states of Central Italy. When Urbino's independence ended it was as a result of being absorbed into the Papal States.

Personality of Federigo:

As a small child Federigo was sent as a hostage to Venice and then was enrolled in school in Mantua. Federigo was the greatest pupil of the finest teacher of the Renaissance, Vittorino da Feltre, who had a boarding school at Mantua under the patronage of Marquis Gianfrancesco I Gonzaga. Among the other students were Francesco da Castiglione, Lodovico Gonzaga, and Taddeo Manfreidi. There Federigo studied a curriculum that included the Latin classics, mathematics, music, art, manners, ethics, and martial arts. The very regime later extolled by Baldassare Castiglione.
Soon after returning to Urbino in 1437 he married in an arranged marriage that had been set since his earliest childhood. Shortly thereafter he started on his first campaign with 800 troops as part of a professional condotierri's army. His task was to learn how to fight battles. It was expected that he would take up the family profession and make a career of being a condotierri captain. As a youth he lost an eye in a tournament as well as sustaining injury to the right side of his face. That is why his portraits always show him in profile from the left. In 1444, at age 22, he suddenly became ruler of Urbino when his half-brother was killed by an enraged mob.
Federigo was a devout Catholic who heard Mass every day. He enjoyed discussing details of theology and religious issues with church leaders. He not only knew Holy Scriptures, but also the early church doctors, whose writings were in his extensive library. Yet he was a man of the age who saw no problem between religious devotion and having four illegitimate children. He was a cultured patron of the arts and is remembered far more for his court of humanists and artists than for his military exploits. He nearly matched his contemporary rival, Lorenzo the Magnificent.
Federigo was a true "Renaissance Man" of the highest order. He set an example few could match. For him the Greek and Roman classics complimented the precepts of Christian religion. He assembled at Urbino the elite of contemporary masters of the fine arts, music, and science. He maintained a choir as well as many musicians. At the same time he excelled at mathematics and all the contemporary fields of natural science.
Federigo epitomized the educational philosophy of his mentor, Vittorino. He was in superb physical condition for arduous field campaigning, yet was refined in all the social graces.
We may quote Castiglione, even though he was living at the court of Federigo's son. "Nor are there wanting many true witnesses still living who can testify to his prudence, humanity, justice, generosity, undaunted spirit, to his military prowess, signally attested by his many victories, the capture of impregnable places, the sudden readiness of his expeditions, the many times when with but small forces he routed large and very powerful armies, and the fact that he never lost a single battle; so that not without reason may we compare him to many famous men among the ancients."

Court life in Urbino:

The palace at Urbino was considered the fairest in all Italy. In addition to the work of Luciano Laurana, Urbino benefited from the attention of Italy's foremost engineer, Francesco di Giorgio. The palace is featured as the finest Renaissance palace in Great Architecture of the World. The Duke furnished it with rich appointments and furniture. Ambrogio da Milano and Domenico Rosselli designed the elaborate ornamentation. Florentine visitors marveled at the tasteful opulence and beauty of the palace and its furnishings. The duke personally conceived of the architectural designs and interior decoration. He was known for his knowledge in this field as well and was considered an accomplished architect. There he held court and contemporaries marveled at the easy way in which he allowed the doors to be open for people to come in and register their complaints and opinions. He felt completely at ease in walking throughout the city unarmed and without the typical bodyguards required by other rulers, assassination being a favorite pastime in Italy. He would visit shops to check on the conditions and needs of the merchants and artisans.
Federigo had one great ambition, to build the greatest library since ancient times. He made collecting books and building a library his special passion. His library from Urbino is now in the Vatican. He kept 30 or 40 scribes busy throughout Europe copying books he could not buy. These he would send to other libraries, for instance at the court of Lorenzo the Magnificent in Florence. He spent 30,000 ducats on the collection. He was helped by Vespasiano who laid out a comprehensive acquisition plan. The Urbino library contained catalogues of the libraries of the Vatican, St. Mark in Florence, Pavia, and Oxford. And he considered that none of the others rivaled his own because the Urbino collections of great authors were complete (Thomas Aquinas, Albertus Magnus, Dante, Boccaccio, Sophocles, Pindar, Menander, Buonaventura etc). It contained every available work on medicine. He commissioned most of the copies and translations of Greek classics. In addition to Greek and Latin works, the library was noted for its extensive collection of Hebrew volumes.
The duke himself was the most learned man at his court. He was classicist but also had mastered most of the science of the time. He was a theologian well versed in Aquinas and Scotus and the fathers of the Eastern and Western Church. He did not much study Plato but knew Aristotle thoroughly. He especially liked the ancient historians and had Livy read to him during meals. Another favorite was Tacitus.
He was a art connoisseur. He employed the finest sculptors and brought the finest tapestries from Flemish looms. His portrait was painted by several of the finest artists including Justus of Ghent. He was noted as a generous art patron. But more important to the tranquility of his realm, he gained the affection of his people. His personal life was frugal and never included extravagant self-indulgence.
Urbino was one of the top cultural centers of Europe. Among the city's favorite sons were Raphael and Bramante. Artists were brought from Spain and tapestry workers from Flanders to beautify the duke's palace.
After the death of his first wife, Federigo married Battista Sforza, who was 13 at the time. She bore him a son and many daughters before dying at age 25. Her influence on court life was extensive, not only because her husband was away at war so much. She was a formidable scholar in her own right. Their daughters married into the Colonna, della Rovere, and Malatesta families.
Court life was rich, if not sumptuous. There were five hundred people in usual attendance. These included several hundred servants, four teachers, an astrologer, the scribes, musicians, and animal trainers. The presence of the astrologer is noteworthy. Astrology was quite the rage throughout Italy at the time and military commanders sought favorable indications from their favorite astrologers before important battles or even before starting marches. Guidobaldo relied on Guido Bonatto for astrology the help win battles and decide on the time to march.

Art of war:

Federigo became an acknowledged master of modern warfare, especially the use of cannon. He developed a delight in the art of generalship for its own sake. He chose as his personal emblem the sword and an olive branch. He was the favorite condotierre hired by Florence. He was also noted for his experience in fortification and siege work. The renowned engineer, Francesco di Giorgio even dedicated his famous book on military fortification to Federigo. Later he was followed as an expert artillerist and fortification engineer by Alfonso d'Este, Marquis of Ferarra, whose cannon won the day at Ravenna in 1512.
A special effort of the period was made in addressing troops on the battlefield. Federigo was considered a master orator and expert in the delivery of classic speeches. He would pass along his line of units as they stood drawn up in order of battle, inspiring them with pride and enthusiasm. He was magnanimous to his enemies and generally sought their surrender to avoid a brutal battle or sack of a town. Most remarkable, he had a well earned reputation for never deserting an ally or switching sides in the middle of a campaign. He never broke his word and was honest and trustworthy. In this he was just the opposite of his principal enemy, Sigismondo Malatesta, and his son's enemy, Caesare Borgia. His contemporary biographers focused on his military exploits, but fashions change, so today hardly a word of that can be found in books on the Renaissance. Instead authors focus on his scholarship and patronage of the arts.
As a condotierri captain his success may be measured by his steady employ in the service of two kings of Naples, two dukes of Milan, and three popes as well as the city of Florence. His reputation for loyalty as well as skill brought him great wealth in fees. He never changed sides until after the completion of the stipulated contract period. For much of his life no other general had the same prestige, not so much for his ability to win great victories, but for his skill in avoiding defeat. His ability to keep strong discipline in his troops was also much appreciated, since so many cities suffered at the hands of their own unruly mercenaries. When faced with battle his usual tactic was to go slow at first, exercising caution, and then when he observed an enemy's mistake or weakness he would strike swiftly.
He early became an expert at conducting sieges and in employing the newly developing cannon. He knew how to transport the heavy weapons across difficult terrain. On campaigns he was personally brave and tireless, sharing the difficulties with the troops.
Among his patrons was the Sforza family of Milan for whom he captured Pesaro while taking Fossombrone for Urbino. He was opposed in many campaigns by Sigismondo Malatesta, Lord of Rimini, whose lands were adjacent to Urbino. It seemed that whichever side hired a Montefeltro, the other side would hire a Malatesta.
In 1448 Federigo raised an army for Florence. For much of his life he was also in the service of the Argonese kings of Naples. This often called him into southern Italy, leaving Urbino open to attack by the Malatestas. On one of these forays Sigismondo also seized papal territory, incurring an excommunication and more of the papal wrath. This gave Federigo, as commander of the papal armies, the opportunity to deal his enemy a serious blow. Federigo captured Fano, taking Sigismondo's heir prisoner, and then took Senigallia also. Sigismondo was forced publicly to his knees to beg forgiveness. While the pope took most of the Malatesta lands, Federigo was allowed to keep fifty towns for Urbino.
Federigo was appointed commander of the papal armies in 1465 with the mission of expanding papal power in the Romagna and Marches. In 1467 he was appointed to command the forces of the league of states organized by Florence to oppose Venice. The main forces of the league were the troops from King Ferrando of Naples and Duke Galeazzo Sforza of Milan. Ferrando sent his son, Alfonso, to command his contingent, while Galeazzo came in person. Machiavelli describes the ensuing campaign in detail. As long as Galeazzo was present the armies only skirmished. The Florentines persuaded him to go home, leaving his troops. With Galeazzo out of the way the Florentines pushed the campaign leading to the battle of Molinella. Machiavelli says this pitched battle, lasting half a day, resulted in no casualties, but only a few wounded horses and some prisoners. This is Machiavelli's typical opinion of condotierri warfare. After the battle, winter weather forced all the participating armies to return to their respective home cities.
After Sigismondo Malatesta died in 1468 Federigo was faced with the problem brought by the pope's desire to take Rimini, which would have surrounded Urbino with Papal lands. Federigo was a devout Catholic, loyal to the papacy, but these popes were trying to capture towns and principalities for their sons before they, the popes, died in office. Thus in 1468 Federigo supported the claim of Roberto Malatesta to Rimini against the pope. As commander of an allied force including troops from Milan and Naples as well, he routed the papal army at Mulazzano.
Lorenzo de' Medici asked Federigo to raise an army in 1472 to capture Volterra for Florence. Federigo brought 10,000 foot and 2,000 horse and occupied the surrounding countryside. He besieged the city, which was located on a steep hill and approachable on only one side. The Volterrans had hired abut 1000 mercenaries to defend themselves. But these troops proved to be not only untrustworthy, but actually dangerous to the citizens. The Volterrans were therefor willing to open the gates, but the Florentine troops got out of hand, giving the city up to a terrible sack. This is the only reported incident of this kind in Federigo's career. He was given a state banquet in his honor in Florence along with precious gifts. Lorenzo took full political credit in Florence for the brilliant victory. Machiavelli was not impressed.
Federigo's military reputation brought Urbino diplomats from as far away as England, Persia, Hungary, and Trebizond.
In 1474 he was received by Pope Sixtus IV with great honor and a military alliance was forged in which Federigo served the pope very well. Machiavelli describes the political background to this appointment in great detail. Federigo was the captain of the Florentine forces. Sixtus and King Ferrando of Naples wanted to form a league against Venice and wanted Florence to abandon its current alliance with Venice and join them. They figured that if they could hire away the Florentine commander they would better persuade Florence to switch sides. The Pope heaped honors on Federigo. He even received the Order of the Garter from the King of England. The Florentines were suspicious and afraid that if they left Venice they would be without allies. So Florence hired Roberto Malatesta, Lord of Rimini, as their new commander. Thus Italy was divided into two camps, The Pope and King of Naples against Florence, Milan, and Venice.
Nothing significant happened for two years. One of the Venetian commanders attacked Sienna, bringing Papal wrath against Florence. But the crisis reached a head in 1476 when the Duke of Milan was assassinated. In Florence the Medici were opposed by the Pazzi family, who were being promoted everywhere by Pope Sixtus. A conspiracy was hatched in 1478 to kill the two Medici brothers and bring papal authority to Florence. The Pazzi and their allies managed to kill Giuliano, but Lorenzo escaped with a wound. At this setback Pope Sixtus and King Ferrando declared open war.
Meanwhile, Federigo had been suppressing rebels in papal lands in Umbria. Then in 1479 he was appointed as chief consultant and advisor to Ferrando's eldest son, Alfonso, who had titular command of the combined Neapolitan and papal forces against Florence. But the Papal and Neapolitan armies attacked along two separate routes. The Papal army passed through Chianti by Sienna laying waste the Florentine territories. It then besieged Castellina. The rapidity of the papal army's advance caught the Florentines still without their forces assembled. The Milanese troops were slow in arriving. The Venetian Senate said they were not obliged to assist Florence because the quarrel was "private" (that is only between Sixtus and Lorenzo d' Medici). Florence hired Ercole Este, Marquis of Ferrara, to command their army. Castellina surrendered after a siege of forty days. Federigo moved on to besiege Arezzo. By this time the Florentine forces were in better order. The campaign ended with the arrival of winter weather. Everyone when home as usual.
War recommenced in the spring. By this time Florence had called up a large array of allies including the rulers of Mantua and Ferrara. They insisted that Venice send Count Carlo with a large number of mercenary troops. The combined Florentine forces were split with the marquis of Ferrara leading one body against the Duke of Calabria's Neapolitans and Count Carlo to oppose the Papal army in Pisan territory. After retaking a number of towns, Count Carlo was sent against Perugia and the rest of the Florentine forces went to Poggibonsi. From there they raided toward Sienna.
Count Carlo suddenly died, leaving Roberto Malatesta as principal advisor to the Florentine commissioner, Jacopo Guicciardini. Roberto led the Florentine army to a great victory over the Papal army by Lake Trasemini. Meanwhile, however, the other sections of the victorious Florentine army led by the Ercole d'Este, Marquis of Ferrara, and Federigo Gonzaga, Marquis of Mantua, got to fighting over the spoils from Sienna. At this Alfonso attacked and routed the Florentines at Poggibonsi. The Florentine army near Perugia had to be recalled to defend the city. The combined Papal and Neapolitan armies continued to press the united Florentine forces and captured Colle.
At this Florence asked for a truce over the winter of 1478-79. Lorenzo d'Medici conceived of a desperate strategy and went in person by ship to Naples to negotiate with King Ferrando. Lorenzo was successful in signing an alliance with King Ferrando, thus breaking Naples away from its alliance with Pope Sixtus. Naturally both Sixtus and the Venetians felt betrayed by their respective allies. This helped bring Venice and the Papacy together into a new combination. At this critical juncture a Turkish army, having been repulsed from its siege of Rhodes, landed at Otranto, in southern Italy. This forced King Ferrando to recall his son, Alfonso, and the Neapolitan army from Sienna to defend southern Italy. The king was also forced to give back to Florence the castles held by Alfonso's army. When Sixtus began to plot with Venice to take Ferrara for one of his nephews, Federigo of Urbino sensed danger and urged the pope to turn his attention to expelling the Turks from southern Italy.
Machiavelli inserts one of his editorial opinions at this point in his history of events. "So it is force and necessity, not promises and obligations, that make princes keep faith."
Fortune made another swift change. Mohammed suddenly died, and civil war in the Ottoman Empire over the succession left the Turkish army in Italy abandoned. Now Naples and Venice were both freed from a Turkish danger and the Pope less interested in uniting Italy in a crusade. The Pope and Venice were allied with Genoa, Sienna, and some other cities on one side and Florence, Naples, Milan, Mantua, Bologna, Ferrara and some others allied on the other side.
Ercole Este, the Marquis of Ferrara, lay sick in bed as the Venetian army approached his city walls. When war over Ferrara began, Federigo sided with Naples and its allies. He was appointed commander of the troops of Milan defending Ferrara from the Venetians. The Venetian commander was Roberto da San Severino (a perennial enemy of Milan). The Florentine commander was Costanzo of Pesaro, who marched to Citta di Castello in Papal territory to restore it to Niccolo Vitelli. Federigo's very son-in-law, Roberto Malatesta, was appointed to lead the papal army, but the two did not have to face each other in battle. Roberto led the papal troops against Alfonso, son of King Ferrando. The King had asked Pope Sixtus for permission to pass the Neapolitan army through the Papal States to march on Ferarra, which the Pope refused. When Roberto Malatesta arrived in Rome, he recommended to Pope Sixtus to hire more infantry, which he did. Alfonso had the Neapolitan army near Rome, within striking distance of Roberto. Once he had the larger army, Roberto made a sudden advance and caught Alfonso before the latter could withdraw in honor. The ensuing battle lasted half a day and was fought more vigorously than any battle in Italy for fifty years, according to Machiavelli. The Neapolitan army was routed, but Alfonso escaped with his Turkish mercenary guard.
Roberto Malatesta died from diarrhea from drinking polluted water and Federigo died of malaria, caught in the swamps around Ferarra. They both died on the same day, September 10, 1482, Federigo in Bologna and Roberto in Rome.
The Pope's effort to follow up his victory by capturing Rimini (left without its Malatesta ruler) and Citta di Castello was a failure. Meanwhile around Ferrara the Venetians were successful against the Duke of Milan and Marquis of Ferrara, now that Federigo was dead. At this Pope Sixtus was pressured into abandoning Venice. He also could see that, if the Venetians took Ferrara, his nephew would not be given the town anyway. This switch enabled a combined Neapolitan, Papal, and Florentine army to reach Ferrara in time to save the city. The allied army numbered 4,000 mounted men at arms and 8,000 foot against the Venetian force of 2,200 men at arms and 6,000 foot. The allies attacked the Venetian navy on the Po River, sinking 200 ships. The Venetians tried a diversion by sending Roberto da San Severino to attack Milan. This ploy backfired as it caused Duke Lodovico to invite the allied army under Duke Alfonso into Milanese territory to attack Venice from a new direction. At the same time the Marquis of Ferrara was able to push the Venetians remaining before his town back the way they had come. Thus by the end of 1483 the allies were moving victoriously on both fronts. The usual winter truce ensued. In the spring of 1484 both sides returned to field campaigning. Venice was down to 6,000 cavalry and 5,000 infantry against an allied force of 13,000 cavalry and 6,000 infantry. Again, fate intervened. Federigo Gonzaga, Marquis of Mantua, died, leaving Lodovico and Alfonso to quarrel between themselves. Venice jumped at the chance and signed a separate agreement with Lodovico in August 1484. Much to everyone else's disgust Lodovico agreed to Venice keeping Rovigo, taken from Ferrara. Machiavelli writes,"Everyone felt they had fought a war which had been costly and which had brought them honor while it lasted but shame by its end..."
Meanwhile the Florentine and Papal forces were attempting to oust Niccolo Vitelli once more from Citta di Castello. The Pope also had to recall his troops from Ferrara to deal with the Colonna and Orsini in Romagna. Sixtus died within days of the end of the war at Ferarra to be succeeded by Innocent III. The new pope continued his predecessor's efforts to suppress the barons of Umbria and the Romagna and to ward off the King of Naples. A new war broke out in southern Italy in which Florence assisted the King of Naples to suppress numerous rebellions. This ended in 1486 with Ferrando victorious and Pope Innocent forced to acquiesce to the situation.


Federigo would have wanted to insure that his son was well educated in the profession of arms. However, Guidobaldo was only ten when his father died at age sixty. His tutor was one of Federigo's nephews, Ottaviano Ubaldini, himself the son of another famous condotierri.
Federigo and Guidobaldo both suffered from gout, but Guidobaldo was always in much the poorer health, having been stricken before the age of twenty. In fact he was often an invalid and was impotent. Castiglione says he could hardly stand at times. Guidobaldo continued both sides of Federigo's career, that of condotierri captain and that of patron of the arts. Despite his infirmity, he was able to maintain rule of Urbino in the style of his father. Aided greatly by his remarkable wife, Elizabetta Gonzaga (see our article on the d'Este women), he devoted all possible financial resources to the arts. The court at Urbino actually reached a greater height of culture and social grace under Elizabetta's control. She is described as being of "pale and heraldic beauty". She was the sister of Francesco Gonzaga, Marquis of Mantua, whose wife in turn was Isabella D'Este of the house of Ferrara.
Their court was filled with the cream of noble society. Guidobaldo was fluent in Latin and Greek and exceptionally well educated and intelligent. Even when his health prevented his engaging in tournaments and military exercises he continued to watch avidly and was always ready to praise or criticize each participant as they deserved with great good judgement. At his court the days passed full of exercises of both body and mind under his watchful eye. Due to illness Guidobaldo generally retired immediately after dinner, whereupon the court life centered around the salon presided over by his wife, Elisabetta. She was renowned for her wit and judgement. Despite her undoubted personal distress at the nature of her barren life, she managed to create an atmosphere that was considered "the very abode of joyfulness". Castiglione calls her "a very great lady." The evening was spent in conversation, games, dancing and musical concerts. Among the company were frequently found some of the top talents of the Renaissance including Ottaviano Fregoso, Federico Fregoso, Giuliano de'Medici, Pietro Bembo, Cesare Gonzaga, Count Ludovico da Canossa, Gaspar Pallavicino and many other nobles.
We can do no better for a picture of Guidobaldo than to quote Castiglione. "Fortune opposed him so in his every undertaking that he rarely brought to a successful issue anything he tried to do; and, although he was very wise in counsel and undaunted in spirit, it seemed that whatever he undertook always succeeded ill with him whether in arms or in anything, great or small; all of which is attested by his many and diverse calamities, which he always bore with such strength of spirit that his virtue was never overcome by Fortune; nay, despising her storms with stanch heart, he lived in sickness as if in health, and in adversity as if most fortunate, with the greatest dignity and esteemed by all."
But he was never robust enough to gain much success on the field of battle, not that he did not give it a great and honorable try. For one thing, by Guidobaldo's time the increasing use of cannon had rendered defense of traditionally fortified cities impossible. For a while, offense took control of warfare. It was not until the art of fortification caught up, with the introduction of the bastioned trace, that defense again came into its own. In the prevailing conditions there was not much Guidobaldo could do to defend Urbino. In fact when the city was faced with the invasion led by Caesare Borgia, Guidobaldo pulled down the antiquated fortifications and fled the city to spare the population from the horrors of a siege. He was amply rewarded for his humanity by the populace when they welcomed him back as a conquering hero after the fall of the Borgias.
Nevertheless, Guidobaldo did his duty to his state and served Kings Alfonso and Ferdinand the Younger of Naples as well as Pope Alexander VI and the civil administrations of Venice and Florence. He was appointed Captain of the Church by Pope Julius II. In 1506, after the campaign had resulted in the capture of Bologna, Pope Julius stopped with his full court at Urbino, where the Duke and Duchess put on a renowned show of hospitality. But it should be pointed out that by selecting Guidobaldo, at once a man of learning but not robust enough to be a great commander, Julius was simply confirming that he would himself lead the Papal armies. This he did, wearing full armor under his papal robes.
Guidobaldo married Elisabetta Gonzaga in 1488 (he was 16). Her portrait, attributed to Mantegna, is in the Ufizi Gallery in Florence. A picture of Guidobaldo as a young boy standing beside his father, who is shown reading a book while in full armor, is in the Palazzo Ducale. The available sources do not indicate what role Guidobaldo played or if he was in action during the French invasion by Charles VIII in 1495. Francesco Gonzaga, Guidobaldo's brother-in-law, commanded the Milanese and Venetian army that attempted unsuccessfully to block Charles during his retreat at Fornovo. That same year he was in the employ of Pope Alexander VI in the minor battles waged to bring the Orsini and other families in the Papal states under control. Alexander appointed his son, Giovanni Borgia, Duke of Gandia, as Gonfalonier of the Church. With the Baglioni, della Rovere, and Vitelli families against the pope Guidobaldo was in the minority on this. The campaigns continued against the backdrop of the simultaneous war between Aragon (Spain) and France waged nearby in Naples. At the Battle of Soriano on 26 Jan. 1497 the Papal forces were defeated and Guidobaldo was taken prisoner. For how long he was held is not mentioned. Naples sent Gonsalvo de Cordova and Prospero Colonna to help the pope. The new French King Louis XII invaded Italy in 1499 and entered Milan, whereupon the princes of northern Italy submitted.
Caesare Borgia had French troops for his first campaign in Romagna that year. The Borgia campaigns against the barons continued for two years gradually taking all the cities around Urbino. In 1502 Guidobaldo loaned his artillery to the pope. Cesare Borgia then marched on Urbino on 21 June and Guidobaldo escaped to Venice. Leonardo da Vinci was the Borgia chief engineer. Machiavelli was sent as emissary of Florence to Caesare at Urbino. In December Caesare tricked and executed four of his lieutenants at Senigallia, and proudly told Machiavelli about it.
A few months later the population of Urbino revolted against the Borgia troops. When Guidobaldo returned, he razed the local fortresses. Machiavelli makes a major point of this in his discussion of the worthlessness of fortresses. When a della Rovere was again elected as pope, Julius II, Guidobaldo was restored to his Dukedom. Raphael painted a St. George to represent Guidobaldo's victory. This St. George may be the one in the National Gallery in Washington, reputed to have been taken by Castiglione as a gift from Guidobaldo to King Henry VII on the occasion of Guidobaldo's investure in the Order of the Garter in 1506. From that time the Garter symbols entered the Montefeltrone heraldry. Guidobaldo was again called to Rome to command the Papal armies. Julius had the same basic idea as Alexander, to suppress the bandit-like baronial families. In 1506 Guidobaldo took official command for the campaign to regain the Romagna and to capture Bologna, but Julius is actually in command throughout. Even with his poor health Guidobaldo was apparently considered an important political, if not military, figure and ally. Otherwise he would not have received such a signal honor as the Order of the Garter. Being childless, in 1504 Guidobaldo named his nephew as heir.

Francesco Maria della Rovere:

Francesco Maria della Rovere (also nephew of Pope Julius II) had been raised at the court in Urbino. He took over when Guidobaldo died in 1508.
The brother of Pope Julius II was Giovanni della Rovere, husband of the heiress of Urbino, Giovanna, sister of the last Montefeltro, Guidobaldo. In 1490 they had a son, Francesco Maria della Rovere. Guilio (Julius) was himself the nephew of Pope Sixtus IV, (Francesco della Rovere). Francesco was appointed as Prefect of Rome by Pope Sixtus IV and again by Pope Julius II in 1502. Francesco held Urbino until it was absorbed into the Papal States. This was accomplished by yet another pope, from the Medici family, Leo X, who wanted the place for a nephew, whom he made Duke. A painting of Francesco Maria della Rovere by Titian showing the Duke in beautiful armor is in the Uffizi Gallery in Florence.
In 1509 Francesco's marriage to Eleanora Gonzaga eldest daughter of Marquis Francesco Gonzaga of Mantua and Isabella d'Este, reenforced the strong ties between Urbino and Mantua. As long as Julius lived Francesco had a powerful patron. He attacked Ferrara for the Pope in 1510. Julius had originally created the League of Cambrai for the purpose of revenge against Venice and to take back territory in Romagna. When France, Spain and the Empire proceeded to nearly eliminate Venetian power, Julius thought better of if and switched sides. He then sent Francesco della Rovere against French forces in Italy. But the French forces were too strong. At that Julius brought in the Spanish. The great battle was fought at Ravenna in 1512. (Francesco della Rovere was likely present but I have not found proof as yet. His relative the Marquis of Pescara was wounded there while leading the Italian horsed arquebusiers. And the Duke of Ferarra's artillery played an important role.)
But with the return of the d'Medici family to the Papacy with Leo X, Urbino became a prize to be added to the Papal states. Leo deposed Francesco in 1516 in favor of his nephew, Lorenzo d' Medici, who thereby became Duke of Urbino and was created Gonfalonier of the Church. Francesco fought vigorously to defend the city but Papal troops took it. Francesco created a army from scratch out of disbanded Spanish and French troops and recaptured Urbino in 1517, but could not hold it. Machiavelli thought this was an extraordinary example of a prince who could raise an army without resources. In another chapter Machiavelli notes with approval that on this campaign Francesco on the way to Urbino left ten enemy cities occupied behind him without fear, again a notable and positive example of good generalship. Francesco was undoubtedly an active and famous commander of the time, but the above sources fail to mention which battles he participated in. During his life war took on a much more violent content than it had during the life of his grandfather. Some of the most bloody, bitterly fought battles took place in northern Italy between 1500 and 1530 and he was likely present at more than one. Francesco died in 1538.
Even before Guidobaldo died Urbino was being swept up as a small bit player in the powerful struggle between France and the German-Spanish combination. When Italy became the battle ground and play ground for the major European powers there was no independent role left for a tiny place like Urbino. Even Florence and Rome were sacked.

Some other personalities:

One of Federigo's daughters was Agnese da Montefeltro, wife of Fabrizio Colonna, grand constable of the Kingdom of Naples and one of the greatest of the military commanders. Their daughter was Vittoria Colonna who married Ferrante Francesco d'Avalos, Marquis of Pescara at age 19 in 1509. He was wounded and captured at Ravenna in 1512 but continued his distinguished military career. She was considered by contemporaries as one of the finest women of Italy.
Ottaviano Fregoso, Guidobaldo's nephew, was elected doge of Genoa in 1513 and was later appointed governor of the city by King Francis I, where he remained until thrown out by the German Emperor in 1522. Castiglione assigns him a major role in the courtly discussions in Urbino in 1507. Apparently he was then resident at the court. Machiavelli notes that Ottaviano razed the fortress of Codera, overlooking Genoa, because he wanted to depend on the goodwill of the population and recognized fortresses were useless. [Was he following the example of his uncle?]
Federico Fregoso, another nephew of Guidobaldo, was created Archbishop of Salerno by Julius II in 1507. He also was resident at Urbino for years.
Constanza Fregoso, sister of Ottaviano and Federico, was wife of Count Marcantonio Landi of Piacenza, and faithful companion of Duchess Elizabetta.
Pope Leo X determined to raise his relatives in power - secured as bride for Lorenzo Medici the daughter of the King of France. Both died young, leaving a baby girl. Their daughter was Catherine de Medici who became queen of France and mother of three kings.
Baldesar Castiglione was born in Casanatico, near Mantua in 1478. He entered the service of Ludovico el Moro, Duke of Milan, in 1496, but returned to Mantua in 1500 when the duke was taken as a prisoner to France. In 1504 he went to the court of Guidobaldo Montefeltro at Urbino.. After Guidobaldo's death he served his successor until 1524. He later went to Spain and died in Toledo in 1529.


Some famous condotierri captains who figure in the times of the Dukes of Urbino included:
Galleazzo Sanseverino, Ottaviano Ubaldini, Antonio Giacomini Tebalducci, Manfreddi of Faenza, three generations of Baglioni of Perugia including Guido, Ridolfo, Gianpalo, Astarre, Malatesta and more; Miclele Attendolo, Jacopo Piccinino, Alfonso d'Este, Francesco Sforza, Paolo Vitelli, Jacopo Caldora, Bartolommeo Alviano, Bartolommeo Colleoni, John Hawkwood, Alberigo da Barbiano, Facino Cane Visconti, Roberto Malatesta, Jacopo Sforza, Boldrino, Pandolfo Malatesta, Filippo Maria Vosconti, Gattamelata, Francesco Gonzaga, Galeazzo Maria Sforza, Boccalino,

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