The Courtly Life of Guidobaldo da Montefeltro in Times of War and Leisure

Italian CondottieriThe Courtly Life of Guidobaldo da Montefeltro in Times of War and...

Son of Federico and adoptive father of Francesco Maria della Rovere. Endowed with great qualities, yet afflicted by chronic ailments—such as gout, which strikes him at the age of twenty. Though inferior to his father in the practice of arms, he surpasses him in civil prudence and counsel. Moderate in spirit during times of prosperity, he displays no weakness in adversity, as seen during the persecution he endures at the hands of the troops of Cesare Borgia. Always active, in moments not devoted to war he habitually overcomes idleness through theatrical performances, triumphal parades, tournaments, hunting, conversations with men of letters, and reading Greek and Latin authors—such as Xenophon and Pliny—in their original languages.

Indice delle Signorie dei Condottieri: ABCDEFGIJLMNOPQRSTUVZ

His role between military campaigns and classical scholarship

Of Gubbio. Duke of Urbino. Lord of Gubbio, Cagli, Urbania, Fossombrone, and San Marino.

Son of Federico da Montefeltro; brother of Antonio da Montefeltro; uncle and adoptive father of Francesco Maria della Rovere; brother-in-law of Fabrizio Colonna, Giovanni della Rovere, Francesco and Giovanni Gonzaga; grandchild of Alessandro Sforza

Born: 1472, June
Death: 1508, September

Year, MonthState, Comp. venturaOpponentCommandArea of ActivityActions Undertaken and Other Salient Facts
1474
Aug.He becomes engaged to Lucrezia d’Aragona (Lucrezia d’Aragona), daughter of King Ferrante of Naples (Ferrante d’Aragona). The contract does not proceed.
1477
Aug.UmbriaHe reaches his father Federico da Montefeltro (Federico da Montefeltro) at the camp of Montone.
1482
Sept.NaplesVenice180 lancesUpon his father’s death, he is nominally retained by the Aragonese to fight the Venetians with a company of 180 men‑at‑arms and 30 broken lances; the Florentines grant him a stipend of 3,600 ducats. The duchy is governed by his half‑brother Antonio da Montefeltro (Antonio da Montefeltro) and his paternal uncle Ottaviano degli Ubaldini (Ottaviano degli Ubaldini). He accompanies the latter on a tour of the duchy to attest to the continuity of government.
1483
Feb.Lazio and CampaniaHe follows his father’s policy by traveling to Viterbo to meet Pope Sixtus IV (Sisto IV) and to Naples to pay homage to King Ferrante of Naples (Ferrante d’Aragona).
1484Pope Innocent VIII (Innocenzo VIII) renews his investiture as Duke of Urbino.
1486
ChurchOsimoMarcheHe serves the Papal State against Boccolino Guzzoni, lord of Osimo.
UmbriaHe disputes with the pope over the fief of Petroio castle, ultimately purchasing it himself rather than granting it to Ugolino Bandi.
Sept.Emilia and RomagnaHe travels to Ferrara and attends horse races at the Barco; meets Ercole I d’Este, Duke of Ferrara; Alfonso of Calabria (Alfonso d’Aragona); Francesco II Gonzaga; and Giovanni I Bentivoglio.
1487
Jan.EmiliaHe is in Bologna for the wedding festivities of Annibale I Bentivoglio.
1488
ChurchRomagnaHe is placed on alert by the papal authorities after the killing of Girolamo Riario at Forlì; tasked with restoring order, he is reported at Cesena amid factional wars between the Tiberti and the Martinelli.
Apr.OddiPerugiaUmbriaHe intervenes on behalf of the Oddi, expelled from Perugia by the Baglioni; provides them lodging first at Gubbio and then in Montefeltro.
UrbinoSassoferratoMarcheHe is involved in a border dispute between Gubbio and Sassoferrato.
Feb.MarcheHe marries Elisabetta Gonzaga (Elisabetta Gonzaga) in the church of San Francesco, Urbino; the marriage contract is dated Aug. 1486 with a dowry of 28,000 ducats.
1489
Feb.–Mar.FolignoPerugiaUmbriaHe defends the people of Foligno against attacks by the Baglioni encamped at Spello; in March he supports their raids in the Spoletino.
Apr.MarcheExiles Perugian exiles from Montefeltro territory at the behest of the Baglioni.
Oct.MarcheIn Pesaro with his brother Antonio da Montefeltro for the wedding of the city’s lord Giovanni Sforza and Maddalena Gonzaga.
1490
Feb.EmiliaIn Ferrara for the marriage of Francesco II Gonzaga, Marquis of Mantua; lodged in the Palazzo Schifanoia.
Mar.–Apr.Umbria and LazioHe departs Gubbio with 250 cavalry and some infantry (including Perugian exiles) to pay homage to Pope Innocent VIII at Rome; hosted by Cardinal Giuliano della Rovere (future Julius II). In late April he returns to his domains escorted by papal family members to the Porta di Santa Maria del Popolo.
1491
JuneOddiPerugiaUmbriaInitially supports the Oddi’s attempt to reenter Perugia against the Baglioni; in June he expels them from his states.
ChurchAscoli PicenoMarcheSends a band of light cavalry to aid the inhabitants of Offida at war with Ascoli Piceno; ordered to join his troops with those of Niccolò Orsini to bring the rebellious city to obedience. The Archbishop of Arles, Giovanni Balve, demands he serve unpaid and relinquish past arrears; he refuses, forcing the pope to revise the order. By September, only 25 mounted crossbowmen remain at Ascoli.
His men become involved in the civil wars of Cesena.
Jul.–Aug.LazioOn the death of Innocent VII, he transfers to the pay of his successor Alexander VI; in August he visits Rome to pay homage to the new pope.
1493
JulyChurchOrsiniUmbriaMoves to support the pope against threats by Virginio Orsini; reported at Gaifana and Valfabbrica; his troops damage territories along their route.
Aug.ChurchGualdo CattaneoUmbriaWith Gaspare da San Severino, he moves to the Bettona plain to support Foligno against inhabitants of Gualdo Cattaneo who refuse to submit to the Folignati.
1494
Jan.Lombardia and EmiliaIn Mantua and Ferrara, received by Duke Ercole I d’Este.
Feb.ChurchOrsiniToscanaIn Tuscany to assist papal forces against Virginio Orsini, who acquired castles from Franceschetto Cybo against the pope’s will.
Mar.NaplesIn the service of King Alfonso II of Naples (Alfonso d’Aragona).
JulyNaplesFranceMarcheRaises 500 mounted crossbowmen to face the French; his men receive pay for only fifteen days.
Aug.Romagna and MarcheJoins Aragonese forces of Duke Ferdinando of Calabria (Ferdinando d’Aragona) on the Savio; moves to Pennabilli with Niccolò Orsini and Gian Giacomo Trivulzio.
Sept.RomagnaLodges at Cesena.
Oct.RomagnaWith Niccolò Orsini and Gian Giacomo Trivulzio, attempts to block enemies near Sant’Agata sul Santerno; the French commander Aubigny breaks Aragonese resistance, forcing Montefeltro onto the defensive.
Nov.RomagnaAt Santarcangelo di Romagna; returns to Cesena to restore order after factional fighting.
Dec.Romagna, Lazio, MarcheLeaves Romagna to move on Monterotondo, territory of the Orsini, to oppose the French advance on Rome; the maneuver fails. Meanwhile Charles VIII reaches Rome, secures papal agreement, and places the Duchy of Urbino under his protection. In the same days Montefeltro acquires Poggio dei Berni from Domenico Doria.
1495
Mar.OddiPerugiaUmbriaArrives at Sigillo (Nocera Umbra) with Girolamo dalla Penna: the arrival of Cardinal Giovanni Borgia forces Perugia’s factions to reconcile on terms onerous to the Baglioni, obliging them to return loot and pay 5,000 ducats to the legate. Montefeltro refuses an offer from the Italic League (800 cavalry, 18,000 ducats) and prefers his agreement with Florence.
Apr.FlorenceSiena, Pisa300 lancesUmbriaContracts at Gubbio with Florence: guaranteed 300 men‑at‑arms in war (250 in peace); term two years plus one of approval; salary 30,000 ducats per year.
JuneToscanaReceived with honors in Florence; lodged in Palazzo Gondi; advances on Montepulciano against Siena, opposed by commissioner Guido da Castell’Ottieri, Jacopo d’Appiano (130 men‑at‑arms), and Giovanni Savelli (80). Montefeltro fortifies at Ponte a Valiano; meeting resistance, he withdraws to confront Pisa.
JulyToscanaCollaborates with commissioner Piero Capponi; gains some success early with Ranuccio da Marciano (despite disagreements); defeats Lucio Malvezzi at Pandera; assaults Ponsacco on the Era with 600 Italian and 100 Gascon infantry; the castle surrenders after three days of artillery, 54 Gascon infantry are killed and mutilated searching for swallowed coins; Italian infantry are stripped before release; Ponsacco is sacked.
Aug.ToscanaOccupies Lari, Peccioli, Lecoli (hangs all surviving defenders by vengeance with Giannone Sampietro), Toiano; negotiates surrender of Palaia after seven days of artillery; attacks Vicopisano; skirmishes near Bientina; forced to withdraw by night and abandon operations.
Nov.ToscanaFrom Poggibonsi moves to Cortona with 300 men‑at‑arms and 1,500 infantry to suppress a conspiracy in favor of the Medici.
Dec.ToscanaAllies with the Entragues, controller of Pisa’s citadel, to attack toward Porta San Marco; Florentine forces enter the borough and clash with Lucio Malvezzi, who betrays the agreement by bombarding the attackers and blocking them; Montefeltro moves to Cascina, where Malvezzi harasses his camp between Settimo and San Casciano.
1496
Jan.Toscana and UmbriaSends his troops to winter at Ponsacco, Pontedera, and nearby castles; at Fonte Becci near Siena with exiles (22 cavalry companies); with Ranuccio da Marciano stays at Palazzo del Diavolo awaiting potential turmoil in the capital; positions before Porta Camollia until abandoning at night toward Val d’Elsa to Castellina in Chianti; travels to Assisi with Giulio Cesare da Varano to broker a truce among factions, acting as surety for the Fiumi.
Feb.Toscana
Mar.ChurchAscoli Piceno300 lancesMarcheDiscontent with Florentine treatment, he resigns early; with papal emissaries’ approval, enters pay of Ludovico Sforza, the pope, and Venice (300 men‑at‑arms; annual salary 30,000 florins). He meets Francesco II Gonzaga at Fossombrone; relieves Fermo from siege by Ascoli Piceno, forcing it to abandon Offida and Ripatransone.
JuneChurchFranceGonfaloniere dello stato della ChiesaUmbria, Marche, AbruzziReappears at Assisi with da Varano amid revived civil strife; receives the papal gonfalon from the legate, Bishop of Conversano; with Giulio Orsini moves to aid Neapolitan King Ferdinando d’Aragona’s troops; reaches the Tronto; with Annibale da Varano penetrates Abruzzi; commands 300 cavalry and 3,000 Abruzzese infantry in the assault on Teramo; with Ruggero Accrocciamuro and Ristagno Cantelmi defeats French under Graziano di Guerres (lo Scarron).
JulyCalabria and BasilicataLeads his militias into Calabria; joins Gonsalvo de Córdoba; captures Laino Borgo and besieges Atella.
Aug.AbruzziLoots the forces of Gian Giordano Orsini and Bartolomeo d’Alviano marching disorderly from Abruzzi toward Rome.
Sept.Abruzzi and LazioAttacks Andrea Matteo Acquaviva in his lands; mid‑month present at L’Aquila for the city’s surrender treaty with Fabrizio Colonna and da Varano; moves on the siege of Gaeta.
Oct.ChurchOrsiniLazioWith Venetian consent (they share his pay), he assists Duke of Gandia Giovanni Borgia, papal Captain General, against the Orsini; in Rome at month’s end with Fabrizio Colonna at a solemn ceremony in St. Peter’s where personal banners and command staffs are delivered and blessed for him and Borgia.
Nov.LazioConquers Campagnano di Roma, Anguillara Sabazia, Galeria, and Sutri; besieges Alviano at Bracciano; is wounded by arquebus shot during an assault.
Dec.LazioCaptures Trevignano Romano (where his men clash with the duke of Gandia’s Spaniards) and Isola Farnese; forced to lift the Bracciano siege.
1497
Jan.LazioFights Carlo Orsini and Vitellozzo Vitelli at Soriano nel Cimino; positions artillery at Anguillara and attacks with light cavalry. Colonna and Antonello Savelli initially rout the enemy and capture Franciotto Orsini and Giovanni Rossetto. Montefeltro deploys German infantry; they are routed by Umbrian pike infantry. Montefeltro is unhorsed and captured by Battista Tosi; Borgia is lightly wounded; Colonna flees to Ronciglione with Cardinal Lunate. All baggage and artillery fall to the victors. Montefeltro is imprisoned first at Soriano nel Cimino and then at Poggio Mirteto.
Apr.VeniceFlorenceLazio and ToscanaReleased under Venetian pressure; must pay his 40,000–70,000 ducat ransom in installments because Alexander VI knows Orsini need that sum to pay 50,000 ducats to the papacy for peace. Montefeltro immediately enters Venetian service.
MayUmbriaReturns to his states; receives 8,000 ducats for his arrears.
Sept.Pope Alexander VI demands payment of the census.
Oct.MarcheBlocked on the frontier by Ranuccio da Marciano and Antonio Maria da San Severino while attempting to move toward Pisa.
1498
Mar.UrbinoPerugiaUmbriaFights the Baglioni; Cardinal Giovanni Borgia intervenes to quell the conflict.
MayOddiPerugiaUmbria and EmiliaParticipates in Perugia’s affairs. Francesco Bigazzino sells him a tower on the Gubbio border also claimed by Giampaolo Baglioni. With Giovanni della Rovere, he again favors his relatives the Oddi against the Baglioni. He enters the Perugian contado from Gubbio and sacks it. The Venetians send him 1,000 ducats to organize his troops; he travels to Ferrara. Papal mediation smooths over the conflict.
JuneHe asks his brother‑in‑law Francesco II Gonzaga in vain for 40 men‑at‑arms and 60 light cavalry.
JulyVeniceFlorence, MilanGovernor General – 200 lancesUmbriaHarasses the Perugian contado to arm his company at its expense. In the castle of Piscine he reconciles with the Comune of Perugia and Giampaolo Baglioni. Meanwhile, negotiations begin with Venice for his next condotta: he requests 30,000 ducats per year and command of 300 lances; Venice offers 20,000 ducats and 200 lances. They agree on 27,000 ducats (including his and his wife’s rations), command of 200 men‑at‑arms (1,000 horse including 100 mounted crossbowmen), title of Governor General, and an advance of 7,000 ducats.
Aug.Umbria and RomagnaOrdered to aid Pisa; receives 3,000 ducats to recruit 1,000 troops. He marches toward the Senese territory, joined by Piero de’ Medici with 200 men‑at‑arms; halted at Fratta Todina by Baglioni and Pandolfo Petrucci. He then heads to Rimini with provveditore Piero Marcello, pausing two days outside the city awaiting an astrologically favorable moment.
Sept.RomagnaMoves through Rezzano into the Lamone valley with 330 lances (including 130 Medici), 100 mounted crossbowmen, and provisions; distances himself from other Venetian captains (Alviano, Manfrone, Bentivoglio) to reach Castiglione di Ravenna, where he has two of his servants hanged—one for entering a peasant’s house, the other for stealing a calf.
Oct.Romagna and ToscanaAt Faenza, with his brother Antonio and Carlo Orsini. From Romagna he sends 500 infantry to Marradi, who seize the borough and besiege its fortress. On arrival of ducal (Gaspare da San Severino) and Florentine (Marciano, Jacopo d’Appiano) forces, the Venetian infantry withdraw. Montefeltro stays defensive, feeling outnumbered; he requests reinforcements after Bibbiena’s fall to Alviano; sends 200 mounted crossbowmen and 60 sappers to occupy Monte della Verna; personally enters Casentino with 700 lances and 6,000 infantry, seizing the region except Poppi (only its mills are destroyed). His advance stops: pay delays and supply issues cause mass desertions.
Nov.Marche and ToscanaAt Casteldelci he demands 20,000 ducats; after recovering from illness, he storms Rassina’s fortress in six hours. He attacks Lierna with artillery; forced to stop by rain.
Dec.ToscanaDemands reinforcements, artillery, and provisions; launches a new assault on Lierna, capturing and sacking the castle: 30 ducats for the first soldier in, 20 for the second, 10 for the third. Of 200 Florentine defenders, 40 infantry and two constables fall. He captures Cesare dal Borgo, seizes arquebuses and 150,000 staia of grain and wine. At Bibbiena he complains of lack of authority over Orsini, Baglioni, and too‑autonomous captains like Alviano; advises a rear‑guard defensive line in Romagna concentrated on Bibbiena with 1,500 infantry and light cavalry. All others oppose him, leaving him isolated; he fortifies Bibbiena with 800 stocked infantry (sending 150 to Alviano) and orders 3,000 men from his states to supply the garrison for eight days.
1499
Jan.ToscanaThe situation at Bibbiena worsens: he sends Luigi da Vilmercate to Ravenna to request 3,000 infantry and to explain the 25‑day shortage of supplies; dispatches Camillo Caracciolo to Venice to report the gravity of his situation.
Feb.Toscana and MarcheSends Morello da Cortona under safe‑conduct from Paolo Vitelli and Gaspare da San Severino to leave Bibbiena due to podagra with 50 horses; arrives at Urbino.
Mar.MarcheSends 1,000 infantry to support Niccolò Orsini’s planned advance into Casentino; promises to return as soon as he is healed.
Apr.MarcheAgain presses for payment of his companies; meets Niccolò Orsini at Casteldelci and sends an envoy to Venice to learn terms for the second year’s respect. The Collegio dei Pregadi debates his dismissal, which is not approved.
June250 lancesVenetoVisits Chioggia and Venice; requests to remain on Venetian pay with title Governor General. Lodged in a Canal Grande palace formerly of the Marquis of Ferrara; escorted by Doge Agostino Barbarigo in the Bucintoro; granted 25 ducats per day for himself and his 200 attendants. Present at the wedding of the doge’s nephew Bernardo Nani; contract renewed for one year of service and one of respect, 12,000 ducats annual. Obligation to provide 100 men‑at‑arms under another captain or 250 lances (including 100 mounted crossbowmen equal to 50 men‑at‑arms) under his own command—in which case pay rises to 25,000 ducats per year.
JulyVenice is at war with Milan: Montefeltro does not join the front, receives three pay installments and 3,000 ducats of his arrears. His substitute in Brescia is Giovambattista Caracciolo with 80 men‑at‑arms and 20 mounted crossbowmen. When Caracciolo is named Captain General of infantry, command of the Feltreschi passes—on Montefeltro’s recommendation—to Morello da Cortona and Giulio Cesare da Perugia.
Sept.–Oct.MarchePope Alexander VI again demands payment of the census; Montefeltro appeals to Venice for aid.
1500
Feb.MarcheStruggles with Papal demands; sends gifts to his Venetian friends for their support (40 deer, roe deer, fallow deer; a boar; various cured meats).
May–JuneVeneto, Emilia, RomagnaReturns to Venice, lodging at Sant’Alvise with the Gradenigo; still received by the doge, but less warmly. Visits Padua and Ferrara, where he is better received. In June he is in Rimini. He falls ill.
JulyMarcheSends an ambassador to Venice to request renewal of his condotta.
Sept.MarcheDemands 20,000 ducats toward his arrears; his ambassador requests 200 ducats for expenses. He is granted 100 ducats against the duke’s pay.
Oct.MarcheThe Venetians pressure him not to aid the lords of Pesaro and Rimini, both under attack by Cesare Borgia; Montefeltro moves closer to Papal service.
Dec.MarcheMeets at Urbino with Giampaolo Baglioni. He expels Perugian exiles from Ponte della Pietra.
1502
Jan.MarcheReceives in Urbino the wedding entourage of Lucrezia Borgia, daughter of the pope, en route to Ferrara to join her husband Alfonso I d’Este.
MarcheHe feels increasingly threatened by papal forces; he allies with Giulio Cesare da Varano of Camerino. Cesare Borgia accuses him of plotting to seize papal artillery while passing through Gubbio.
JuneUrbinoChurchMarche, Romagna, LombardyDespite having delivered artillery in April for Camerino’s conquest, he is expelled from his duchy by papal orders. Naively convinced by his kinsman Piero Antonio da Urbino, acting for Borgia, he surrenders artillery, troops, provisions, and free passage, effectively handing over Urbino. At night 10,000 papal troops enter Urbino; he escapes disguised with a small escort through the dark countryside toward the Rocca of San Leo to join his nephew Francesco Maria della Rovere, only to find it also in enemy hands. With the aid of Dionigi Agatoni, he reaches Sant’Agata Feltria; sends his nephew to the Florentine territory in Val di Bagno, dismisses his mounted crossbowmen, and sets out alone on an ass to the mountains due to gout, accompanied by three companions and shepherd guides promised 200 ducats. He evades an ambush on the Borello stream, loses all his money, and reaches Castelnuovo in the Ravenna territory. Local authorities initially refuse him entry to San Giorgio; a Venetian order then allows him, disguised with 30 horse, to enter Ravenna. He proceeds to Mantua seeking help from Francesco II Gonzaga, but in vain.
JulyLombardyIn Vigevano and Milan, he petitions King Louis XII of France for protection.
Sept.VenetoIn Venice, supported by the state, first at San Stae and then at Carmagno.
Oct.CondottieriChurchVeneto and MarcheLeaves Venice, lands at Senigallia, and reaches San Leo with 10 horse; sends his nephew Ottaviano Fregoso to Magione on Lake Trasimeno to ally with Paolo Orsini, Vitellozzo Vitelli, Giampaolo Baglioni, Ermes Bentivoglio, Oliverotto da Fermo, Guido Pecci, and Antonio da Venafro on behalf of Pandolfo Petrucci. He rebels against papal forces and retakes nearly all the duchy’s fortresses.
Nov.Marche and UmbriaMeets Vitellozzo Vitelli at Castel Durante (Urbania); occupies Gubbio, imprisoning followers of Valentino; enters Urbino to popular acclaim. With Muzio Colonna, aids Giovanni Maria da Varano in occupying Camerino. Despite gout, he reaches Fano to meet Paolo l’Orsini, unable to dissuade him from reconciling with Borgia. He recovers the fortresses of San Leo, Maiolo, Sant’Agata Feltria, and San Marino, dismantling their walls and relocating artillery and his personal belongings there. His men raid the Rimini countryside.
Dec.Marche and UmbriaAgain abandons Urbino to escape Cesare Borgia’s designs; takes refuge at Fossombrone with 2,000 persons, then moves to Perugia and Città di Castello.
1503
Jan.Toscana, Emilia, VenetoAfter the sudden killings of Vitellozzo Vitelli and Oliverotto da Fermo at Senigallia, he flees to Siena, Pitigliano, Montefiore, Buonconvento, Fucecchio, Montecarlo, Lucca, and through the Garfagnana to Bologna; lodged at the Osteria del Montone, he is ignored by the Bentivoglio for fear of Borgia. He then travels to Rovigo and Venice, where the Collegio immediately recognizes him with a monthly stipend of 100 ducats and a house in Cannaregio for his stay.
Sept.Veneto and MarcheOn the unexpected death of Alexander VI, he borrows 3,000 ducats, leaves Venice via Ravenna and Meldola, and returns to Urbino.
Oct.VeniceChurch100 lances and 150 light horseMarche and RomagnaFormalizes his relationship with Venice for one year of service and one of respect; is granted 10,000 ducats as advance and promises of aid to recover his lands—in return he offers to raise 2,000 infantry. At the head of 8,000 mercenaries he immediately captures the rocche of Senigallia, Santarcangelo di Romagna, and Savignano sul Rubicone (sacked). He also seizes Verucchio, Roncofreddo, Monte Urano, Carpineta; threatens Cesena and raids nearby territory. He attacks Santa Maria del Monte and plunders the contado of Bertinoro and Forlimpopoli. He is defeated in a skirmish near Cesena by forces from Imola under Guglielmo Tempione and Giovanni Spiga, wounded in the back (40 dead and 200 wounded among the Venetians). In revenge for a lieutenant’s death, he orders the execution without arms of 40 infantry from Forlì and Forlimpopoli. He occupies Santa Maria del Monte with 200 cavalry and 1,200 infantry; repelled at Fano, he retreats to San Marino to join Pandolfo Malatesta against Rimini. Shortly thereafter Cardinal Raffaello Riario, Cardinal of San Giorgio, approaches him, inviting him to facilitate the Riario’s return to rule Forlì and Imola. He concludes a ten‑day truce with Cesena.
Nov.ChurchCaptain General and Gonfaloniere dello stato della ChiesaRomagna, Umbria, LazioRecaptures Savignano sul Rubicone lost at Cesena. Upon election of Cardinal della Rovere as Pope Julius II, he requests permission to go to Rome for the coronation; before departing he cedes Santarcangelo and Savignano to the papacy (not Venice) as agreed, and delivers Verucchio and Cesenatico to Venice. Stricken by gout at Gubbio, he sends Venice 1,000 infantry under Lattanzio da Bergamo and 200 light horse under Giulio Vitelli. He passes through Perugia to Rome: asks for Forlì’s delivery, where Borgia has amassed spoils. He is appointed Captain General for four years, Gonfaloniere dello stato della Chiesa, and Duke of Romagna.
Dec.LazioTo please the pope, he meets Cesare Borgia in the Vatican, where Borgia is imprisoned.
1504
Jan.RomagnaAttempts to obtain Cesena’s fortress from Borgia’s men; seeks to moderate Pope Julius II’s hostility toward Venetian occupiers of Rimini and Faenza.
Feb.Requests the balance of 10,000 ducats for past pay from Venice; 2,000 ducats are sent.
Mar.ChurchOrdelaffiRomagnaSeizes Forlimpopoli and besieges its fortress; moves against Ludovico Ordelaffi at Forlì with 1,200 infantry and 400 cavalry; raids livestock and sends an envoy demanding the surrender of the Rocca of Ravaldino.
Apr.300 lancesLazioGranted a condotta of 300 men‑at‑arms—80 under Gaspare da San Severino and 80 under Costantino Arianiti.
MayLazioAdopts as son his nephew Francesco Maria della Rovere and is invested with the Order of the Garter by English ambassadors.
JuneRomagnaGranted an annual stipend of 5,000 ducats. Under papal pressure he abandons the Venetian alliance; travels to Cesena, lodged in the palace of Niccolò Guerra da Bagno with 200 cavalry, then moves into the Forlì region.
July–Aug.RomagnaTakes possession of Forlì. Bartolomeo Morattini hands over the Rocchetta di Schiavonia still held by Ordelaffi partisans. At month’s end he returns to Forlì, lodging in the Borgo of Ravaldino with Giovanni Gonzaga, preparing new siege engines. Negotiations conclude with Consalvo di Mirafonte surrendering the main Rocca. Despite severe gout, Montefeltro rides thrice through the city. He recovers his renowned library stolen by Borgia, though not other valuables. He returns to Cesena and reviews his troops at Bertinoro.
Sept.RomagnaIn Cesena.
Dec.LazioReceives 4,000 ducats; travels to Rome with his nephew; lodged by Cardinal Ippolito d’Este at Santa Maria del Popolo.
1505
Jan.LazioIn Rome; continues to suffer from gout.
Feb.Lazio and UmbriaActs as peacemaker between the pope and Venice; also supports the Baglioni. Attends the troop review by Francesco Maria della Rovere at Campo de’ Fiori; visits Orvieto as guest of the Bishop of Sutri.
Aug.MarcheAt Urbino, he musters his troops in Montefeltro.
1506
Apr.RomagnaIn Cesena, attends the ceremony ratifying the general peace among factions.
Aug.–Sept.ChurchPerugia400 lancesMarche, Lazio, UmbriaMusters infantry at San Leo; leaves Rome with Pope Julius II, 24 cardinals, and 400 lances; reaches Orvieto; at his insistence, convinces Giampaolo Baglioni to surrender without fighting and hand over his sons Malatesta and Orazio as hostages. He escorts the pope to Perugia and Castel della Pieve; lodged in the house of Pietro Paolo della Cornia. He returns to Urbino, where the pope enters with 100 stradioti and 300 halberdiers. He commands 400 lances to fight Bentivoglio of Bologna; half of the company nominally under nephew Francesco Maria della Rovere but in fact under Ambrogio da Landriano.
Oct.ChurchBolognaRomagna and EmiliaIn Cesena (hosted by Guerra da Bagno) reviews 1,000 infantry; travels to Forlì, Imola, and Faenza with Pope Julius II; campaigns alongside Francesco II Gonzaga against Bentivoglio.
Nov.Emilia and RomagnaAccompanies Pope Julius II on his solemn entry into Bologna after Bentivoglio’s flight to Milan; at Imola with the pope.
1507
Feb.EmiliaSuffers a violent gout attack in Bologna.
Mar.Romagna and MarcheAccompanies the pope on visits to Imola, Forlì, and Urbino; helps reconcile factions in Fano: Bartolomeo Ercolani, Malatesta Boccacci, and Angelo dei Palazzi.
Apr.LiguriaIn Genoa for the entry of the city just reconquered by French arms under King Louis XII.
MarcheWith Giovanni da Sassatello, intervenes to calm the spirits of Pesaro exiles hostile to Giovanni Sforza.
1508
Feb.MarcheFalls ill overnight at Fossombrone of podagra.
Sept.MarcheDies overnight at month’s end of podagra at Fossombrone. His solemn funeral takes place in Urbino Cathedral; he is buried in the Franciscan church of San Bernardino opposite his father Federico da Montefeltro. The funeral office is held before five bishops of the duchy with clergy and 825 mourning and hooded gentlemen. Eulogy by Ludovico Odasio of Padua, his former tutor and secretary. Portraits by Raphael (Palazzo Ducale, Pesaro), Marco Zoppo, and Bartolomeo della Gatta (Galleria Colonna, Rome). Central figure with his wife Elisabetta Gonzaga in Baldassarre Castiglione’s Il Cortegiano. Castiglione also composes for King Henry VII of England the epistle De vita et gestis Guidubaldi Urbini ducis, a panegyric of the late duke. His court hosts Pietro Bembo; friends include Jacopo Sadoleto, Bernardo Dovizi, Bernardo Accolti, Tebaldeo, and Michelangelo Buonarroti. Vespasiano da Bisticci dedicates his Vita di Federico to him; Giorgio Benigno Salviati dedicates Federicus, de animae regni principe; Cristoforo Landino submits to him at age ten his Interpretationes on Horace; Piero della Francesca dedicates Libellus de quinque corporibus regularibus; mathematician Luca Pacioli his Summa de arithmetica. Portrait by Bartolomeo della Gatta (Galleria Colonna, Rome); portrait with his father Federico by Pedro Berruguete.

-“Dotato di grandi qualità, ma vittima di perpetue infermità e disgrazie.. La corte di Guidobaldo, come scuola della più elevata cultura, è stata resa immortale da Baldassarre Castiglione, il quale fece rappresentare la sua egloga, il Tirsi, dinanzi a quella società quasi per renderle omaggio, e più tardi collocò i dialoghi del suo Cortegiano nel circolo della coltissima duchessa, Elisabetta Gonzaga.” BURCKHARDT

-“Era stato homo amatore del culto divino, et avea le inzegne spicolativo; buon gramatico, buon oratore et gram teiolico; dell’astrologia al molte se ne dilectava..Home neutrale, costumato et amabile ale più persone. Et era de bona statura, bianco e colorito.” BERNARDI

-“Del suo non troppo innalzarsi sì nell’arti del governo come in quelle della milizia, benché continuamente esercitata, possono chiamarsi in colpa e la brevità del suo vivere e la debolezza di sua salute, essendosi trovato podagroso nell’età di vent’anni.” POLIDORI

-“Imitatore ed emulo delle virtù paterne, fu stupore del suo secolo e operò tanto in pochi anni, che poteva bastar al corso d’un lunghissimo tempo.. Fu egli nell’esercizio dell’arme di gran lunga inferiore al padre, ma nella prudenza civile, e nel consiglio, o eguale o forse superiore a lui.. Nimico per natura dell’ozio.. passava virtuosamente il tempo, spendendolo ora nelle cacce, alle quali si sentiva grandemente inclinato, ed ora nelle giostre, ed altri esercizi militari; e non era minima parte delle sue delizie fra gli studi delle cose della guerra, il piacere ch’egli prendeva della conversazione degli uomini letterati, de’ quali aveva sempre piena la corte.” BALDI

-“Felicissimo duca di Urbino per le sue incomparabili qualità ..Coraggioso e prudente..Huomo costumato, virtuoso e letterato.” SANSOVINO

-“Che non fu meno che il padre si fosse, in ogni maniera di virtù eccellente.” TARCAGNOTA

-“Se in Guidobaldo la militare perizia e il valore di Federico non mancarono, mancò la fortuna, perché nelle sue imprese di guerra gli volse quasi sempre le spalle.. Fu Guidobaldo, di viso piuttosto lungo e bianco, ma colorito; ebbe fina e distesa capigliatura, bionda in fanciullezza, ma poi tendente al rosso, collo sottile, larghe le spalle, petto rilevato, ventre piano, cosce ben formate, gambe alquanto scarse ma non indecenti; di statura alta anzi che no; e prima che la podagra lo tormentasse, graziosissimo portatore di sua persona. Di eleganti vesti e di molle acconciatura non si curava, sì della nettezza e decenza: aveva l’aspetto fra il severo e il piacevole: pronunciava con difficoltà alcune lettere; ma quel difetto non guastava, né impediva che non fosse dolce e grazioso parlatore come il padre. Non conobbe paura, e gli si ascriveva a difetto che si perigliasse nelle battaglie più che a capitano si addicesse.. Fu di animo moderato nella prosperità; nelle avversità invitto. Fedele alle promesse, come il padre; non odiatore, non persecutore, anzi generoso co’ nemici. Pio, clemente e giusto principe: fu dottissimo in ogni genere di letteratura, e specialmente in greco che maneggiava come la propria lingua, prediligendo sopra tutti Senofonte.” UGOLINI

-“Lui mi pare una gentil cosa et fuor di mia opinione truovo che è acuto dicto et di grandissimo discorso et sentimento.” DOVIZI

-“Uomo di valore e di buon senno nelle battaglie.” COLUCCI

-“Virtuosissimo e splendidissimo principe.” CIMARELLI

-“Aveva ereditato da suo padre Federico la gotta non certo il genio militare, e l’afflizione per questa malattia, aggiungendosi alla sifilide, penalizzava Guidobaldo al punto che a volte non riusciva neppure a montare a cavallo.” SHAW

-“Giovane per le lettere più che per arme prestantissimo.” CERRETANI

-“Capitano e principe in quell’età di eccellente virtù.” PORZIO

-“Guidobaldo de Montefeltre était un bon prince. Aucun, dans toute l’Italie, n’était plus aimé de son peuple, envers qui il montrait une bonhomie affectueuse et paternelle. C’était un homme cultivé, un protecteur  des arts, et fort hereux dans la splendide bibliothèque de son palais d’Urbino.”

-“Guidobaldo non potrà “cum foemina coire numquam in tota vita”, non sarà mai “ad rem uxoriam” idoneo. Così si esprime P. Bembo, nel tracciare il profilo di Guidobaldo, dopo la sua morte.. Segnato, sin dall’adolescenza, da un’ombra di malinconia e di tristezza Guidobaldo, è solito dopo la messa dare udienza ogni giorno ai sudditi, quindi gironzolare un po’ per il centro porgendo orecchio alle suppliche, per poi discuterne e, anche, risolverle consultandosi con i più fidi consiglieri. E’ con siffatto impegno quotidiano che si stempera quella sua pena sempre meno segreta agli occhi dei suoi interlocutori. E’ sopportabile, ad ogni modo, la pena se Guidobaldo si intrattiene con altro e con altro si diverte. Le rappresentazioni, le recite, i carri trionfali, le giostre, la caccia, la conversazione con i letterati, le letture di autori greci e latini, specie di Senofonte e di Plinio.” BENZONI 

-“Il Signor Guido Ubaldo, o per difetto di natura, o più tosto, come esso credea, per malie che fatte gli fussero non poté in tutto il tempo di sua vita conoscer donna carnalmente, nè il matrimonio exercitare.” BEMBO 

-“Un gentiluomo vecchio stampo, sofferente di gotta dall’età di vent’anni, che univa ad una buona cultura umanistica il piacere dell’ospitalità.” DAL MONTE

-“He served as a captain.. He did not, however, share his father’s military genius or his energy.” BARTLETT

-“La corte di Urbino toccò in quegli anni la sua ultima perfezione e divenne quasi espressione di una ideale società ove la gentilezza e la cortesia avessero trovato la loro serena dimora…Ed era naturale che il ricordo di quella favolosa età non si cancellasse più dagli animi ch’eran vissuti nel cerchio magico di quel sortilegio, e che quel ricordo viva ancora nel genio di Baldassarre Castiglione, che figurò quell’ideale di umanità e di cortesia nel suo Cortegiano.” FRANCESCHINI

-Il suo sepolcro riporta la seguente iscrizione “D.O.M./ Guido Ubaldo Federici Feltris Urbino duci III/ Qui adhuc impubes paternam gloriam aemulans/ Imperia viriliter feliciterque gessit./ Iuvenis de adversa tryunphans fortuna/ Sed vi morbi corpore debilior animo vegetior./ Pro armis literas, pro militibus viros lectissimos/ Pro re bellica rem aulicam./ Ita coluit, fovit, auxit/ Ut ejus aulo ceteris praeclarissimum./ Extet exempla/ Suo XXXVI/ Et Elisabethae Gonzagae mirae pudicitiae faeminae/ Ipsi ingali amore et egregia virtuti/ Conjunctis.”

Specific Biographies

-B. Baldi. Vita e fatti di Guidobaldo duca d’Urbino.

Featured image: wikipedia

Roberto Damiani
Roberto Damiani
Roberto Damiani è l'autore del sito Condottieri di ventura.