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Biographical notes on War Captains and Mercenary Leaders operating in Italy between 1330 and 1550

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Paolo Orsini: Ambition and Betrayal in Medieval Italy

Italian CondottieriPaolo Orsini: Ambition and Betrayal in Medieval Italy

Paolo Orsini, at times both friend and foe of various popes, of King Ladislao of Naples (Ladislao d'Angiò), Duke Gian Galeazzo Visconti of Milan, of Florence, of Perugia, and of the condottieri Braccio da Montone and Muzio Attendolo Sforza. He is considered disloyal for switching allegiances multiple times. Ambitious, haughty, determined, and bloodthirsty, he was not always successful on the battlefield, but he was always a valiant captain. As mentioned, often a traitor, he was treacherously killed by his traditional adversaries, the Colonna family

Indice delle Signorie dei Condottieri: ABCDEFGIJLMNOPQRSTUVZ

Paolo Orsini’s Tumultuous Career: Shifting Loyalties Among Italy’s Elite

Paolo Orsini, from the Gallese branch. Count. Lord of Gallese in Teverina, Olevano Romano, Narni, Orvieto, Tuscania, Canino, Marta, Montalto di Castro, Fiano Romano. Cousin of Gentile Orsini.

Born: 1369
Death: 1416, August

Year, monthState, Comp. venturaOpponentConductActivity AreaActions taken and other salient facts
1387ChurchAntipopeAbruzzo, LazioHe fought in favor of Pope Urban VI against the Count of Manoppello. Towards the end of the year, he destroyed the castle of La Villa, twenty miles from Rome, where previously the condottiere Giovanni Beltoft had been severely wounded by peasants.
1390ChurchColonnaLazioHe played an important role in opposing the bands of Sciarra Colonna and others who, right after the Jubilee, harassed the Papal States with their bandit-like actions.
AutumnChurchAntipopeLazioAlongside Mostarda da Forlì, he helped Pope Boniface IX return to Rome; he forced the Colonna to flee into the countryside. His presence became crucial in curbing the excesses of Giovanni Colonna and Onorato Gaetani, who were open supporters of the antipope Benedict XIII.
Apr.ChurchComp. venturaLazioHe was in Sutri with 1000 cavalry; there he faced Ceccolo Broglia and Brandolino Brandolini. The mercenaries tried to drive him out of the area.
………ChurchExiles, FermoMarcheHe opposed the rebellious cities in the March of Ancona that were defiant to the Papal States, as well as the bands led by Mostarda da Forlì, Luca di Canale, Piero da Castel Modenese, and Neri da Faenza.
Dec.Comp. venturaFlorence, Lucca650 cavalryTuscanyHe joined forces with 650 cavalry in the company of Alberico da Barbiano to invade Tuscany. He burst into the territory of Lucca.
Feb.MilanLucca, FlorenceTuscanyHe stationed himself near Siena, waiting for the outcome of a conspiracy plotted against the Florentines at San Miniato. He coordinated with Ottobono Terzi and Ceccolo Broglia, left the Pisan area, and entered the countryside of Lucca to join forces with Giovanni da Barbiano and raid the entire territory hostilely. Blocked by the Luccans on the Serchio at San Quirico di Moriano, he retreated, laying waste to the territory.
Mar.TuscanyAlongside Paolo Savelli, Ceccolino dei Michelotti, and Giovanni da Barbiano, he followed Alberico da Barbiano on a raid that took them to the very gates of Florence.
MayFlorenceMilan400 lancesTuscanyHe received 12,500 florins from the Florentines and switched to their payroll to fight against the Viscontis. He left the ducal forces, led by Michelotti with 200 cavalry; he was granted a command of 400 lances.
JuneTuscanyHe arrived at Colle di Val d’Elsa; he opposed Alberico da Barbiano, who was stationed in the Sienese area. Together with Filippo da Pisa, he supported Bartolomeo Boccanera in the Pisan and Livornese territories against the orders of Bernardo della Serra. During a raid, the condottieri seized two thousand two hundred head of livestock and took many prisoners; they approached Pisa, near the village of San Marco. They unsuccessfully requested to speak with Vanni d’Appiano. No one confronted them.
JulyLombardyIn the context of Italian medieval history, particularly during the era of the condottieri, the term “Maresciallo di campo” refers to a high military rank, essentially equivalent to a Field Marshal. This position was often held by experienced military leaders responsible for the command of a substantial portion of an army, orchestrating maneuvers, and strategic engagements during warfare.
Aug. – Sept.Lombardy, TuscanyHe distinguished himself in the battle of Governolo against Jacopo dal Verme. In September, he returned to Tuscany; along with Bernardo della Serra and Giovanni Colonna, he stormed into the Valdarno with 2,500 cavalry and another 3,000 men comprising infantry and sappers; they set fire to numerous houses in Cascina. From Pisa, 500 cavalry and many infantrymen came against them, laying an ambush for the Florentines. Orsini crossed the river, ravaged the Pisan area around Campo and Cesanello, and reached the capital. He set up several ambushes nearby; some men came out from Pisa with whom he had several minor skirmishes that culminated in the capture of twelve men-at-arms. He then returned to the Florentine territory. He reached Lucca with 300 cavalry to repel the Pisan militias that were plaguing the area. He entered the city and made his way back to San Miniato.
Oct.TuscanyHe was still in Lucca with Giovanni Colonna and 1,000 cavalry; his forces were also joined by 170 Luccan lances. They rode to Filettole, which was sacked; the same fate befell Nodica, Vecchiano, Malaventro, Santa Maria di Castello, and Ponte a Serchio. Approaching Pisa, they crossed the Baldo Bridge and engaged the opponents. He spent the night at Santa Maria di Castello, then headed towards Vicopisano, besieging the town until he was forced to return to San Miniato.
Mar.ChurchPerugiaUmbriaHe returned to the service of Pope Boniface IX. Following the assassination of Biordo dei Michelotti in Perugia, he allied with Mostarda da Forlì and Ugolino Trinci to expel the followers of the Raspanti party from Perugia, as well as from Assisi, Spello, Todi, Nocera Umbra, Gualdo Tadino, Trevi, Cesi, and Orvieto.
Apr.FlorenceMilanTuscanyHe carried out a raid for the Florentines in the Pisan territory with 400 lances and 1,000 infantry shortly before a truce was signed between the republic and the Viscontis. He encamped near the village of San Marco, just outside Pisa. He was wounded in a skirmish with enemies led by Giovanni da Fighino and Astorre Visconti.
JuneChurchPerugia1500 cavalryTuscany, UmbriaHis dues, as well as those of Bernardo della Serra and Giovanni Colonna, were settled in Florence. He received 10,000 florins, including an extra one and a half times his usual pay; in return, he committed not to harass the territories of the commune for a certain period. The Perugians also sent him a sum of money to have him as an ally against the papal forces: conversely, he led 1,500 cavalry into their territory and devastated the counties he passed through. He forced the inhabitants to accept the return of the pope.
Mar.Comp. venturaPerugiaUmbriaHe raided through the Perugian area, looted livestock in the Chiugi region, and took prisoners.
Sept.MontemarteComp. ventura400 lancesUmbriaHe was in Orvieto with 400 lances when two hundred pilgrims dressed in white robes arrived. He joined them and for several days transformed himself into a pilgrim as well; he was seen with his men barefoot, whipping themselves with crosses in front of them while singing praises to the Lord. Mid-month, he returned to his old warrior life; leading 100 cavalry, he joined forces with Francesco da Montemarte, who commanded another 100. Together, the two captains went to Fabro where he convinced 90 infantrymen of Bernardo della Serra to abandon Fichino and return the locality to its inhabitants after receiving a ransom of 550 florins.
Nov.Comp. venturaPollenzaMarcheHe harassed Mostarda da Forlì in Montemilone (Pollenza).
Jan.ChurchAntipopeLazioGiovanni and Nicola Colonna attempted to incite Rome in favor of the antipope Benedict XIII against Boniface IX. Orsini rushed to the pope’s defense and attacked Palestrina with 2,000 cavalry. For his merits, he was awarded the vicariate of Olevano Romano.
Oct.ChurchRebelsMarcheHe was sent by the pope to the Marche region along with his brothers Giovanni and Poncello, and his cousin Gentile Orsini, to confront the local rebels.
1401ExilesViterboLazioHe assisted the Gatti family in gaining control of Viterbo. He was appointed Rector of the March; he would hold this position until 1406. Also in that year, he obtained Gallese from Giovanni and Nicola Colonna.
…………TuscanyIn Florence, the commune sought an alliance with the Papal States to combat the Viscontis.
JuneIn Venice, there was a discussion about the advisability of granting him a military commission (condotta); the proposal was ultimately rejected.
JulyChurchMilanTuscanyHe captured Manfredo Barbavara but soon left the theater of operations because, due to the plague, the ducal troops were unable to forcefully descend from Lombardy.
Aug.MarcheHe was in the March of Ancona, where his salary was advanced by the Jewish communities of Fano and Fossombrone on behalf of the Apostolic Chamber.
Sept.ChurchMilanUmbriaHe burst into the Perugian region alongside Braccio da Montone, Mostarda da Forlì, and Conte da Carrara under the command of Giannello Tomacelli. They all encamped near the capital, effectively keeping it under near siege.
Oct.UmbriaHe joined forces with the Florentine and Bindo da Montopoli under the Papal captains. Their militias set up their encampments between Olmo and San Mariano. The nearby countryside was raided.
Jan.UmbriaHe was defeated near Assisi in a three-hour battle by 1,200 to 2,500 cavalry commanded by Ottobono Terzi. Among the Papal forces, there were 150 casualties.
Mar.Boniface IX authorized him to collect the salary owed to him for the command of 490 lances directly from the lords obligated to pay the annual census to the Apostolic Chamber (Antonio da Montefeltro, 1300 florins for Urbino, Gubbio, and Cagli; Charles, Pandolfo, and Malatesta Malatesta, 8000 florins for Rimini, Pesaro, Fano, Cesena, Osimo, and other lands; Ugolino Trinci, 1000 florins for Foligno, Montefalcone, Bevagna, and other lands; Rodolfo da Varano, 1000 florins for San Ginesio and other lands; Guido di Matelica, 300 florins for Matelica; Raniero Simonetti and brothers, for Jesi, Serra San Quirico, and Accola; Chiavello Chiavelli, 450 florins for Fabriano; Onofrio Smeducci, 400 florins for San Severino Marche; Giovanni and Bernardino Cima, 400 florins for Cingoli; Monaldo da Montevecchio and brothers, 775 florins for Montevecchio and San Lorenzo in Campo; Onofrio Paganelli, 50 florins for Montalboddo; Matteo di Branca, 25 florins for Cartoceto; the municipality of Città di Castello, 1500 florins).
MayUmbriaHe returns to the countryside of Assisi with Count da Carrara (Conte da Carrara) and Mustard of Forlì (Mostarda da Forlì). He enters the capital with the help of Averaldo de Nepis.
JuneMarche, Emilia, LombardyHe moves from the March of Ancona with 400 lances and 600 infantrymen and relocates to Emilia. In the cathedral of Ferrara, he attends the ceremony where Nicholas d’Este (Niccolò d’Este) is presented with the baton of the general captain. Together with Cardinal Legate Baldassare Cossa (the future antipope John XXIII), and Alberico da Barbiano, he rides in the Parma area, captures many prisoners, and raids a lot of livestock. He crosses the Po River; meets in Cremona with Ugolino Cavalcabò who incites the papal forces to invade the Milanese territory.
July – Aug.Emilia, Lombardy, RomagnaIn Umbria, he obtains from the castellan of Assisi, after a long siege, the two city fortresses in exchange for 1000 florins. In Lombardy, he joins Alberico da Barbiano in devastating the Pavia area; he continues to follow him between Castel Bolognese and Faenza. He stops in the Bologna area and sets up camp on the Idice River, 8 miles from the capital; every day he leads his raids right up to the gates of Bologna. He breaches the wall of a small tower between the Porta di Strada Castiglione and that of Santo Stefano and enters the city. He is repelled by the counterattack of Facino Cane; with the support of 1200 horses and the backing of Nicholas d’Este, Uguccione Contrari, and Charles Malatesta (Carlo Malatesta), he repels the opponents with heavy losses. During the same days, with Charles Malatesta, he forces the lord of Imola, Ludovico Alidosi, to abandon the alliance with the Visconti. With the Peace of Caledio, Orsini enters the citadel of Bologna.
Sept.Emilia, MarcheHe stays a few days in Bologna in command of the garrison. At the end of the month, he is reported to be in Tolentino. By October, he is reported to be in Fermo.
Feb.ChurchGozzadiniEmiliaHe besieges Massumatico with Conrad of Matelica (Corrado di Matelica); having captured that castle, he gains control of Castel Fiuminese, Galliera, and Cento. Together with Richard Pepoli (Riccardo Pepoli), he besieges the Gozzadini in Pieve di Cento. Nanne Gozzadini is forced to flee to Ferrara.
Mar. – Apr.Boniface IX orders Giovanni Tomacelli, grand chancellor of the Kingdom of Sicily, to recall Paolo Orsini to the service of the Papal States. In April, the pope requests Andrea Tomacelli, rector of the March, and his treasurer Andrea de Summa, to impose a levy of 50,000 florins on the region to provide for the salaries of Paolo Orsini.
JuneChurchRossiEmiliaHe is sent to Parma to assist the lord of the city, Ottobono Terzi, against the Rossi family and the Florentines; he enters Parma where he is welcomed with grand illuminations.
Aug.The pope insists that archbishops, bishops, abbots, clerics, and Jews of the March (who have shown considerable reluctance) also contribute their share to the levy in order to pay the dues of Paolo Orsini.
Oct.ChurchCunioRomagnaHe takes possession of Faenza, surrendered to the Papal States by Astorre Manfredi. Subsequently, Paolo Orsini assists Manfredi against attacks brought against him by Alberico da Barbiano.
Nov.EmiliaDuring the same period, he manages to purchase half of Fiano Romano with the support of his brother-in-law, Giovanni Sanguigni, abbot of San Paolo: he will enjoy the possession after two years. He is in Bologna and participates in a joust given in honor of the new pope Innocent VII: he wins the tournament alongside Galeazzo Pepoli.
JuneChurchCunioRomagnaHe resumes the conflict with Barbiano; he besieges Manfredo da Barbiano in Castel Bolognese: he attacks the supply men of the opponent. Attacked in turn, he counters this captain with the help of Charles Malatesta (Carlo Malatesta) and Astorre Manfredi.
Mar.ChurchNaplesLazioHe is recalled to Rome by Pope Innocent VII to confront the Colonna family and the militias of the King of Naples, Ladislaus of Anjou (Ladislao d’Angiò).
Aug.LazioThe Roman populace demands that Paolo Orsini not enter the city for the entire grape harvest period. During the same days, the pope’s nephew, Ludovico Migliorati, kills 11 representatives of the Roman community who had come to complain to Innocent VII about nothing being done to end the schism tearing apart the Church. The pope is forced to flee from Rome to Viterbo. Orsini joins forces with Mustard of Forlì (Mostarda da Forlì), Ceccolino dei Michelotti, and Beccarino to confront the Colonna family who have taken control of the city. He defeats Giovanni Colonna at the Prati di Nerone, who was defending Borgo Leonino; he enters the Vatican: Pieretto de Andreis and Gentile da Monterano are driven back into the Campagna.
Sept.ChurchCunio, NaplesRomagna, LazioHe returns to confront the Barbianos in Romagna: a fifteen-day truce among the belligerents is brokered by Nicholas d’Este. Upon its expiration, he begins the construction of a bastion nearby and returns to Rome. No longer wanting rivals by his side, by the end of the month, he does not hesitate to kill Mustard of Forlì (Mostarda da Forlì) with his own sword (or to have him killed by Antonio Orsini, assisted by his relatives). The murder occurs in a room of the Apostolic Palace in front of the pope himself. Paolo Orsini then lays siege to Castel Sant’Angelo.
Oct.MarcheMid-month, he is reported to be in Fermo with Ludovico Migliorati and Ceccolino dei Michelotti.
Nov.LazioHe seizes part of Castel Sant’Angelo and orders the palisades defending the fortress to be set on fire.
Jan.PerugiaExilesUmbriaHe was led for a month by the Perugians following threats to the city from Braccio di Montone.
Apr.ChurchNaples500 lancesLazioThe Pope grants him a command of 500 men-at-arms; his salary is always drawn from the revenues of some vicariates in the Marche region. With Migliorati, he resumes the siege of Castel Sant’Angelo; he consistently opposes the Roman barons allied with the king of Naples.
MayLazioHe leaves the camp with his company towards Sant’Anastasio at the Tre Fontane, where he sets up his encampments. With the Romans, he attacks Castel Giubileo, which surrenders after a day: the defenders flee the area by night.
JuneLazioHe transports a large quantity of wheat to Rome. At the end of the month, Ladislaus of Naples (Ladislao d’Angiò), who was declared deposed from the throne by Pope Innocent VII, reconciles with the pontiff; at Tor di Mezza, near Albano, a truce of eleven days is agreed upon between the Orsini on one side and Pieretto de Andreis and Count of Carrara (Conte da Carrara) on the other.
July – Aug.Standard-bearer of the State of the ChurchCampania, LazioHe travels to Naples with Ludovico Migliorati; he returns to Rome in the early days of August with the peace treaty. He is appointed Standard-bearer of the State of the Church: he pays his men two wages with the promise of giving them another two in a few days. Pressure is exerted on him and Migliorati by the Florentine ambassador Rinaldo degli Albizzi to prevent them from taking up arms in favor of the Pisans.
Sept. – Oct.LazioIndeed, he is contacted by the Pisans who offer him 40,000 florins and the lordship of all the lands around the capital. The negotiations continue until early October when Pisa falls into the power of the Florentines. During this period, he is noted in Rome and Viterbo.
Dec.ChurchLazioHe is present in the Basilica of St. Peter at the ceremonies held in honor of the newly elected Pope Gregory XII to the pontifical throne. He switches to his payroll.
Jan.Comp. venturaChurch2000 cavalryLazioIn Rome, his credit with the Papal States amounts to 60,000 florins. To recoup his losses, he targets Corneto (Tarquinia) and seizes several castles; he asks the inhabitants of Toscanella (Tuscania) to allow his troops within the city walls; 400 cavalrymen enter and are housed in homes throughout the area. He also goes to Tuscania and makes himself lord under the pretext of a possible betrayal: the city is sacked. 500 citizens are robbed and imprisoned with several deaths; there is no reaction from the papal authorities.
Apr.Naples, PerugiaTaranto, ExilesApuliaHe joins Ladislaus of Naples (Ladislao d’Angiò) at the siege of Taranto. The operations cease when the King of Naples accepts the advice of Gentile da Monterano to marry the besieged Maria d’Enghien, widow of Raimondo Orsini del Balzo. Orsini is tasked with delivering the wedding ring to the woman. The Neapolitan troops enter the city. Also in that month, for a sum of 1000 ducats, he is led with 1000 horses by the Perugians to counter the exiles. Braccio di Montone must abandon the territory and retreat to Rocca Contrada (Arcevia).
MayChurchNaples500 lancesLazioHe is enlisted by the papal forces with 500 active lances and 50 dead ones (the latter being a sort of reward for troops listed on the payroll but not present in the ranks). He is promised the settlement of his credits claimed against the Bolognese and the Estensi and a monthly commission of 550 ducats. Each lance is granted a monthly wage of 12 ducats if the operations are confined to the March of Ancona, the Duchy of Spoleto, the Patrimony, the Roman countryside, the Maritime Province, Sabina, and the Roman Campagna; a monthly wage of 18 florins per lance is foreseen for actions to be carried out in the Bolognese, the Ferrarese, and the Florentine areas. Paolo Orsini commits to delivering the outlaws (those who are subject to a ban, the banned) that are captured by his men.
JuneLazioNeapolitan troops enter Rome with the Colonna through a breach in the walls near Porta San Lorenzo. The pope takes refuge in Castel Sant’Angelo; Orsini bursts into the Vatican from Castel Valca, and the following day he defeats his opponents at the same gate. Fires of joy illuminate the city because in his hands have fallen Nicola and Giovanni Colonna, Antonio Savelli, Jacopo Orsini, Corradino di Antiochia, Riccardo Sanguigni, and Galeotto Normanni: the last three are beheaded in the Capitol. With the victory, Pope Gregory XII assigns him the revenues of Romagna and other provinces, grants him the vicariate of Tuscania for a five-year term in exchange for the census of a hunting dog, and the vicariate of Narni. The pontiff does not possess the 60,000 florins necessary to settle his dues and is thus obliged to also grant him the castles of Collescipione, Canino, Marta, and Montalto di Castro; on this occasion, the pope must pledge his own tiara to some Florentine bankers for 4700 florins to address his financial difficulties.
Aug.LazioIn Rome, the people rebel; he intervenes with Niccolò Orsini and restores order in the Capitol. Pope Gregory XII travels to Viterbo and Savona to attend the council that must decide who should be considered the true pope between him and Benedict XIII. Orsini remains in Rome as the General Captain of the State of the Church.
…………LazioDuring the year, he is granted a total salary of 93,000 ducats by the Apostolic Chamber.
Jan.LazioRome rises up once again following a tax of 30,000 florins imposed also on the clergy by the vicar cardinal Pietro Annibaldi Stefaneschi: the tax increase irritates the population, the streets are increasingly infested with thieves, and a column of one hundred pilgrims is massacred by soldiers of Orsini who have turned to lawlessness.
Mar.PerugiaExilesUmbriaHe is led by the Perugians with more than 1000 horses to once again counter the guerrilla warfare conducted by the exiles. He repels the opponents and is granted 1000 ducats; he is promised a similar annual annuity.
Apr.ChurchNaplesLazioLadislaus of Naples (Ladislao d’Angiò) attacks Rome again with an army of 12,000 cavalry and numerous infantry. Paolo Orsini has the walls strengthened with dense palisades of logs; together with Beccarino, he repels the enemy attacks at San Paolo multiple times. At his disposal are only 2000 cavalry and a few infantry. When the Neapolitan galleys force the passage of the Tiber and seize the castles defending the river, he meets with Pieretto de Andreis and Count of Carrara (Conte da Carrara) near Trastevere: after a few days, the Angevin militias can enter Rome. Their entry is probably “facilitated” by the delivery in his favor of several thousand ducats: Orsini entrusts all the bridges and city gates to the royal troops while a cardinal surrenders Castel Sant’Angelo. He participates in a solemn religious ceremony in the palace of San Paolo outside the walls, attended by Ladislaus of Naples himself and all his commanders; immediately afterwards, he leaves Rome with the aim of reaching Castel Valca.
MayUmbriaIn the Perugian region.
JuneUmbriaHe remains stationed in the Perugian region with Pieretto de Andreis, Giacomo Galgano, Count of Carrara (Conte da Carrara), Giovanni Colonna, Gentile da Monterano, and Ciucio di Paterno. He presses the Perugian authorities on behalf of a fellow citizen, Fazio di Tommaso, who has served under his command and ensures his readmission to Perugia. He camps with other captains in the Todi area: the community allocates 150 florins for his comfort supplies.
JulyUmbria, LazioHe remains stationed in the Perugian region with Count of Carrara; then he targets Tuscania (which had been captured from him by Tartaglia); he moves to Rome: some companies of Perugian infantry are transferred to guard this latter city.
Sept. – Oct.OrsiniNaplesLazioHe incites the Romans to rebel, outraged that Giannotto Torti has been chosen for the position of senator. He goes to the Capitol, captures the senator elected by the King of Naples, and defeats the Angevin captains, among whom Francesco di Catania is killed. Paolo Orsini establishes his residence at Santo Spirito; he moves between Galeria, Formello, and Bracciano.
Jan.UmbriaHe reconciles with Ladislaus of Naples (Ladislao d’Angiò). He is noted in Foligno with Pieretto de Andreis. Here, he is met by some Perugian ambassadors.
Apr.NaplesFlorence, AntipopeTuscanyHe is with Tartaglia heading towards Valli near Siena. The cattle raided are taken to the lands of Count of Pitigliano, Bertoldo Orsini. He must abandon the operations following some skirmishes.
JuneTuscany, UmbriaSubdues Cortona with Pieretto de Andreis; he remains there on guard. Mid-month, he is still near the city; he attends the investiture ceremony of Anglona (Tursi) in favor of Antonio di Sangro. He proceeds to Certaldo, conducts his raids as far as Arezzo, and enters Perugia. From there, with Giovanni Colonna (300 cavalry), he attempts to join forces with Gentile da Monterano to surprise Malatesta Malatesta at Bagno Vignoni: the action fails because it is Monterano who falls into an ambush.
JulyFlorence, AntipopeNaples, Church600 lances, 200 infantrymenUmbriaHe halts the advance on Rome from Orvieto by the enemy army and prevents their provisioning: when attacked, he is tempted by the offers and money from the Florentines to switch sides and serve antipope Alessandro V and the Florentines themselves. The pretender to the throne of Naples, Luigi d’Angiò, lands in Pisa in the same days. Paolo Orsini reaches an agreement with the adversaries four days before the expiration of his contract; only on the last day does he notify his change of allegiance to the King of Naples through a herald. The antipope acknowledges the fiefs already recognized to him by Gregorio XII; he is granted a command of 600 live lances (and 60 dead ones) and 200 infantry (including 100 crossbowmen). He receives a personal provision of 600 florins: the expenses are shared equally between the Florentines and the antipope.
Sept. – Oct.LazioIn September, he enters Rome. He lodges with his men alongside those of Luigi d’Angiò in the Borgo di San Pietro. In October, two of his attacks on the city fortresses are repelled by Pieretto de Andreis.
Nov.LazioHe assaults Castel Sant’Angelo with 300 lances and 200 infantry: after setting fire to the gate of the Santo Spirito hospital, he clashes with Betto da Lipari, capturing some of his armored soldiers; de Andreis and Nicola Colonna are forced to take refuge in Santo Spirito.
Dec.LazioMalatesta Malatesta waits at Sant’Agnese towards San Lorenzo. That same night, Paolo Orsini enters the Borgo Leonino, which is sacked; Pieretto de Andreis counterattacks him. Orsini then leaves the portico of San Pietro with Jacopo Orsini and exits with his men-at-arms and infantry through Porta Torrione (Porta Cavalleggeri); he ascends the hill leading to Porta San Pancrazio, descends towards San Giacomo in Settignano (San Giacomo alla Lungara), and surprises de Andreis near Porta Settimiana, which closes off Trastevere. On the last day of the year, he goes to the Capitoline Hill and returns to the portico of San Pietro, where he had taken lodgings nearby.
Jan.LazioRome rises in support of the King of Naples; Paolo Orsini orders the destruction of the fortifications prepared by the adversaries in Santo Spirito; he has the resulting materials transported to San Lorenzo outside the walls to build a bastion in front of the gate still occupied by the Neapolitans. The defenders of this gate surrender after a few days due to the fire from three bombards. Orsini penetrates Trastevere with Lorenzo Annibaldi; with other members of his household, he crosses the Bridge of the Jews (Ponte Sisto) and heads towards Campo dei Fiori, where he finds the people gathered: he declares that the previous government is dissolved and installs new officials in place of the old ones. He attacks Porta Maggiore.
Feb.LazioHe participates in a celebration at Testaccio in Rome. The defenders of Porta Maggiore surrender: thus, the last enemy bulwark is also eliminated.
Apr.LazioIn Rome, he takes part with the Beccarino in the feast of San Giorgio.
MayGeneral captainLazioAppointed as Captain General of the State of the Church, he continues the war with great zeal. With the death of Alessandro V, he returns to Rome with Jacopo and Niccolò Orsini. He moves to the Roman countryside, conquers Tivoli and Ostia, and forces the Colonna and Savelli families to surrender.
JuneLazioLeading 1500 cavalry, he defeats 5000 cavalry and 3000 infantry of the Durazzo faction in Rome, at the Prati di Nerone. The adversaries are forced to retreat and seek refuge at the monastery of Fossanova near Priverno.
JulyLazioHe leaves Rome through the Porta di Castel Sant’Angelo; he rides towards the countryside to meet Cardinal of Santa Prassede, Fernando di Frias; he accompanies him into the city; he enters Rome through the Porta di San Pancrazio.
Aug.UmbriaHe attracts numerous men-at-arms from the company of Muzio Attendolo Sforza (100 cavalry) with generous promises to bring them to Narni.
Sept.Lazio, AbruzzoIn Rome with Luigi d’Angiò: he lodges in San Pietro with Sforza and Monterano. He leaves the city through the Porta di Castel Sant’Angelo and reaches Viterbo. The campaign continues wearily as Orsini’s credit towards the antipope amounts to four months’ pay. He is defeated at Tagliacozzo by Guidantonio da Montefeltro.
Oct.He is given 30,000 florins out of the 44,000 requested by Orsini.
Nov.UmbriaHe assaults the Porta di San Pietro in Perugia at night with Braccio di Montone and Sforza leading 2000 cavalry and 300 infantry. Repelled by Tartaglia’s defense, he withdraws to winter in his own estates.
Dec.EmiliaAt Bologna, he is with antipope Giovanni XXIII, Luigi d’Angiò, and Jacopo Orsini.
Mar.Emilia, TuscanyStill in Bologna, he leaves the city through the Porta di Santo Stefano with the antipope, Luigi d’Angiò, and Niccolò d’Este; he enters Siena through the Porta di San Marco and heads towards Florence.
Apr.LazioHe arrives in Rome from the Maremma on the eve of Easter. He is present at the ceremony where the banners of Luigi d’Angiò’s army are blessed on the occasion of the feast of San Giorgio.
MayLazio, UmbriaHe defeats Ladislao d’Angiò’s troops at Roccasecca. The victory is caused by a fortunate pincer movement executed by Sforza and Luigi di Loigny, which prevails over the vanguard of the enemy army and disrupts their rear guard. Despite the victory, he opposes Sforza’s plan to pursue the fleeing adversaries for fear of falling into ambushes. The King of Naples seeks refuge in San Germano (Cassino), manages to gather the remaining troops, and finds the money for the ransom of prisoners; after a few days, Ladislao d’Angiò has at his disposal an almost identical force as before. For these events, Paolo Orsini is immediately accused of treason by Sforza and Luigi d’Angiò due to the lands he owns in Puglia. The condottiero moves to Umbria; with Montone and Sforza, he routs Ceccolino dei Michelotti and Tartaglia at Torgiano. 600 enemy cavalry are captured, and many Perugians, taken prisoner, are forced to ransom themselves.
JuneLazioWith the signing of the peace treaty of San Felice, he returns to Rome and organizes a grand feast at the Navicella outside Porta San Paolo with his wife. Also present are Tartaglia, Braccio di Montone, Muzio Attendolo Sforza, and Giovanni Colonna.
Aug.UmbriaHe is seriously wounded in the eye by an arrow while leading an assault on the castle of Santa Giuliana.
Nov.TuscanyHe captures Nanni di Spinello along with all his men at Colle di Val d’Elsa.
………UmbriaHe goes to Orvieto and supports the faction of the Mercurini against the Beffati, who fear his ambition; he takes Sassoferrato from Carlo Malatesta. With his actions, he causes Sforza to defect to the opposing side.
JuneOrsiniAntipopeMarche, LazioGiovanni XXIII concludes a peace with the Neapolitan sovereign and refuses to consider Paolo Orsini (with all the related consequences) among his allies. Upon learning of the lack of clauses in his favor, the condottiero distances himself from the March of Ancona and heads towards Rome. He enters the city with the help of his supporters through a breach in the walls near Porta Capena. The antipope, lacking sufficient forces, flees from the city.
Aug.LazioHe arrives at Bolsena with 100 lances and strengthens the city garrison.
Sept.EmiliaHe manages to reconcile with Giovanni XXIII; at the beginning of the month, he is in Bologna (with an escort of 150 cavalry) alongside the same antipope.
Jan.ExilesViterboLazioHe assaults Viterbo. He assists the abbot of Farfa and San Martino del Monte in breaking the wall of the palace near the Porta di San Pietro (also known as Porta di Salciccia) at night to penetrate it against Giovanni Gatti. The exiles seize this gate and that of San Sisto. The next morning, the abbot advances to the square of the Fontana del Sepale, while Riccio dei Capocci pushes towards the district of Santa Maria in Poggio. Initially, the population does not react; however, when they realize that Riccio dei Capocci’s infantrymen begin to sack some houses, they take up arms and, under the leadership of Giovanni Gatti, oppose their entry. The two main leaders of the exiles are captured. Of these, the abbot is killed in prison by the same infantrymen who accompanied him on the enterprise; for this reason, these soldiers will be released. Riccio dei Capocci, captured at San Giovanni in Zoccoli, is instead hanged the following day with another 18/28 infantrymen of an Orsini company, along with their constable Giovanni Starli, at the rings of the Palazzo del Podestà. The Orsini, who are stationed nearby, seeing the outcome of the action, withdraw with all their men.
Feb. – Mar.AntipopeChurch, NaplesMarcheHe returns to the March of Ancona with 1600 cavalry. He meets his brother Giordano, the legate of the antipope in the March, and Ludovico Migliorati in Macerata.
Apr.MarcheHe arrives at Montegiorgio with 1000 cavalry; he connects with Migliorati, builds a bastion, and besieges Monterubbiano. Angevin militias, under the command of Sforza, reach Caldarola and Sarnano; the two captains prefer to withdraw.
MayMarcheHe hands over the fortress of Montegiorgio to Ludovico Migliorati and dispatches 200 cavalry and 100 infantry for the garrison of Macerata, Mogliano, and Petriolo. The inhabitants of Macerata, who adhere to the party of Gregorio XII, refuse to let these troops enter the city, preferring to submit to the rule of Rodolfo da Varano. Paolo Orsini heads towards Cingoli and Montesanto (Potenza Picena); from there, he heads towards Rome. He gets lost in the woods, and his path is blocked by the enemy. He is besieged in Arcevia by Malatesta Malatesta, Muzio Attendolo Sforza, Conte da Carrara, and Guidantonio da Montefeltro. He is saved by the intervention of Braccio di Montone.
June – JulyUmbriaHe joins forces with Braccio di Montone at Ponte Pattoli and confronts Ceccolino dei Michelotti, Muzio Attendolo Sforza, Conte da Carrara, Malacarne, and Fabrizio da Capua for forty days without seeking a pitched battle.
Aug. – Sept.MarcheHe returns to Arcevia, which he abandons overnight with the connivance of Malatesta Malatesta. He reaches Florence, where 40,000 florins necessary to resume the war are handed to him. He then moves to Orvieto with 100 lances.
AutumnHe is challenged to a duel by Muzio Attendolo Sforza; initially, he accepts but ultimately, even in that circumstance, he avoids direct combat in the fencing match.
Nov.Umbria, MarcheHis attempt to seize Orvieto through a treaty fails. He moves to Urbino, also because Montefeltro now supports the cause of the antipope.
………Umbria, LazioWith Braccio di Montone, he defends the cause of the antipope in Umbria and in the Papal States.
MayUmbriaHe is convinced by Ladislao d’Angiò to join his troops with the Neapolitan army that is advancing from the Tiber Valley towards Perugia: he is led for six months. The king promises not to seek revenge for his previous betrayal. By royal will, he reconciles with Sforza, although there are reports of an assassination attempt against him by Sforza himself and Giovanni Mostarda, son of Mostarda da Forlì.
JuneUmbriaHe arrives at Montefalco with Micheletto Attendolo; he moves from Bevagna towards Foligno; with Sforza, he besieges Lorenzo Attendolo, who defends it with Ugolino Trinci, but without success. He recaptures Sant’Angelo di Celle, San Martino in Campo, and other castles; he besieges, again with Sforza, Montone in Todi.
JulyUmbria, Lazio, CampaniaHe is among the allies of the King of Naples in the peace treaty concluded by Ladislao d’Angiò with the Florentines at the bridge of Petrignano in the territory of Assisi. In the same period, he is lured to Perugia with false promises; he is accused of treason by Sforza; Paolo Orsini, along with Orso Orsini, Niccolò Orsini, and Rosso dall’Aquila, is imprisoned. Ladislao d’Angiò orders Sforza and Pier Bertoldo Farnese to occupy his domains with 1000 cavalry. Paolo Orsini is first taken to Ponte Pattoli; he is then embarked at Gaeta on the same fleet that accompanies the king to Naples; he is imprisoned in Castelnuovo. He is sentenced to death.
Aug.CampaniaThere is an ineffective intervention in his favor by Antonio Acquaviva; he is saved from execution by the sudden death of Ladislao d’Angiò. Later, in the same Neapolitan prison, he is joined by Sforza.
Dec.Campania, Lazio, UmbriaHe is released upon the payment of a ransom of 30,000 florins. Giulio Cesare da Capua, the Michelotti, and the Count of Fondi, Cristoforo Gaetani, have requested clemency for him.
Nov.NaplesLazioHe returns to Rome with 700 cavalry to restore the authority of Queen Giovanna d’Angiò of Naples. He enters through the Porta Salaria and immediately begins to undermine Cardinal Giacomo Isolani, who resides in the Palazzo di San Lorenzo in Damaso.
Dec.ExilesViterboLazio, Umbria, TuscanyHe imprisons Francesco Orsini in Rome, who will be released after a few days to be sent to Monterotondo. Orsini occupies Narni, Terni, and Orte with Neapolitan militias; in Rome, he asserts his dominance by demolishing the wall of the Ponte di San Pietro and removing unnecessary fortifications from Castel Sant’Angelo. As always inconsistent, at the end of the month, he returns to the service of antipope Giovanni XXIII; he goes to Florence, and the people of Perugia send him 120 baskets of wheat, much appreciated during a period characterized by severe famine. He attacks Viterbo once again with the exiles; he camps at Casale del Tesoriere and Santa Maria del Paradiso. He breaks the wall of the Emperor’s palace overnight. His men are spotted by a guard while scaling the walls, so he is forced to retreat with Niccolò Orsini. There are many skirmishes at the Tower of San Francesco and the Porta di San Matteo until, after eight days, he has to leave the area.
Feb.UmbriaIn Spoleto.
………PerugiaMontone1000 cavalry, 200 infantrymenUmbriaIn Narni, he is called upon for assistance by the people of Perugia, who provide him with 3000 florins to counteract Montone, who is infesting the municipal territory with exiles from the noble party.
JuneUmbriaHe moves to join forces with Carlo Malatesta, crosses the Tiber, and reaches Otricoli and Narni. The people of Terni attempt to block his path, but a skirmish is enough for him to continue towards Perugia. Braccio di Montone retreats to Narni.
Aug.UmbriaHe fords the Nera and encounters Braccio di Montone, who has defeated his allies at Umbertide/Sant’Egidio. He is treacherously killed by Tartaglia, Cristoforo da Lavello, and Ludovico Colonna at Colfiorito, a castle of the Trinci in the Foligno area, while discussing with them around the walls with a small escort. His troops confront the enemies but are overwhelmed by the intervention of Bracceschi forces. He is portrayed in Florence in the Guafonda by Paolo Uccello in the gardens belonging to the Bartolini Salimbeni with Ottobono Terzi, Luca di Canale, and Carlo Malatesta. He marries Rita Sanguigni.


-“Amico e nemico alla perugina Repubblica, amico e nemico a Braccio, non sempre fortunato, ma sempre valoroso condottiero.” FABRETTI

-“Vedi quel che sapea tutte le vie/Di Roma esser ministro, e molte volte,/Moltiplicando in onoranza e fama,/E fu Paolo Orsin, se ben m’ascolte.” Cambino Aretino riportato da FABRETTI

-“In Paolo si univa la riputazione d’essere un prode Condottier d’armi, ed insieme il discredito d’uomo disleale.” MURATORI

-“Uomo di buono stomaco.” BIGNAMI

-“Condottier d’armi di molta celebrità nel medio evo, che servì a vicenda e gli amici e i nemici, e per meglio dire, che secondo l’uso dei tempi, mantenendo a sue spese molte squadre, serviva chi gli faceva migliori patti.. Era Paolo gran nemico di Sforza di Cotignola, perché in Roma non voleva rivali, e tanto era geloso della sua potenza e della sua dignità, che le violenze per conservarle gli erano famigliari. Non voleva udir lodi degli altri, era altiero, insolente, sanguinario, e alla presenza del papa nel 1405 ammazzò il Mostarda condottiero distinto.” LITTA

-“Uomo della maggior autorità che fosse stato da mill’anni in quella città (Roma), perché era amato e stimato per la grande opinione che si avea del valor suo.” DI COSTANZO

-“Huomo di molto valore, e giudizio nell’armi.” CAMPANO

-“Lo più magnifico capitano che mai nell’età che corre se possa recordare.. homo de troppo gran fatti, che papa re et onne gran signore de Italia lo temevano et lo tenevano con losenghe.” PETRONE

-“Capitaneus magnus gentium.” ANNALES FOROLIVIENSES

-“Vaillant capitaine de gens d’armes.” J. DES URSINS

-“Capitano valoroso.. Percioché egli era valoroso in guerra, ma ambitioso, insolente, sanguinoso e infame per leggierezza di cervello, e per esser più volte vituperosamente passato da una parte all’altra.” GIOVIO

-“Notabilissimo homo d’armi.” P. DI MATTIOLO

-“Invitto Capitano del suo secolo.” COMPAGNONI

-“Capitano di valore, ma sempre facile a vendersi.” PAGNANI

-“Valoroso Capitano qual i maggiori e più segnalati de quei tempi.” PELLINI

-“Illustre capitano di quei tempi.” PERUZZI

-“Questo barone era valoroso in guerra, ma un poco ambitioso, colerico e sanguigno.. Era l’Orsino di pelo castagniccio e di alta statura.” ROSCIO

-“Nel quale rilusse grandissimo honor di virtù militare..Egli era nelle guerre coraggioso, e sapeva con fortezza superare ogni difficoltà, con prudenza a prevedere i partiti, e con vigor d’animo e di valoroso corpo entrar nelle schiere armate, ma tanto insolente, sanguinario e tanto ambitioso.” SANSOVINO

-“Quo nullus erat inter ductores illustrior.” BILLIA

-“Celebre condottiero del secolo XV.” BOSI

-“E’ un bastardo de messer Francesco de Jordanu dal monte delli Ursini de Roma, et ène el magiur caporale de gente d’arme de nostro pagese.” ZAMPOLINI

-Con Mostarda da Forlì, Brandolino Brandolini, il Tartaglia e Tommasino Crivelli “Nell’armi riescirono maestri espertissimi.” P. BONOLI

-“Valorosissimo capitano, che apprese il mestier dell’armi sotto la disciplina di Alberigo da Cunio.” COLUCCI

-“Uno dei più esperti e valorosi Capitani del secolo, che meritatamente godea riputazione di gran militare.” ACQUACOTTA

-“Celebre capitano e mercenario altrettanto mutevole.” GOZZADINI

-“Fu strenuo condottiero ed anche abile diplomatico.” BRIGANTE COLONNA

-“Generosus et strenuus vir.” DELAITO

-“Famosissimo capitano.. El breve dil capitano Paulo Ursino: “A papa e curiali tenne el freno; né mai el mio stendardo in diretro volsi.”” BROGLIO

-Con Jacopo Orsini “Tamquam sapientes homines armorum.” DI PIETRO

-“Colui, ch’i re domò, la Patria vinse/ Pien di valor, d’ingegno, e di potenza;/ Braccio crudel, con l’altrui braccio estinse.” Da un sonetto di autore incerto ripreso dal ROSCIO

-Con Paolo Savelli, Ceccolo Broglia, Brandolino Brandolini, Luca di Canale e Ceccolino dei Michelotti “Cohortium praefecti insignes.” PLATINA

-“Fu.. abile gestore delle compagnie di ventura dipendenti dalla sua persona, servendo a vicenda amici e nemici e propendendo alternativamente verso coloro che offrivano accordi più vantaggiosi.” FALCIONI

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Other image: wikipedia

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