Pope Benedict XI (1303-4)

Pope Benedict XI, the first Dominican pope, inherited a difficult political situation.  His attempts to deal with the Colonna cardinals who had undermined his predecessor, Pope Boniface VIII, made him unpopular in Rome, and he fled to Perugia.

Benedict XI was a great benefactor of the Dominicans of Perugia, to whom he gave formal ownership of the church of San Stefano del Castellare (which was next to their convent and it church, which is now known as San Domenico Vecchio).  He also granted plenary indulgences to those celebrating Mass there on the feast of St Stephen (August 3rd).  This would have attracted large numbers of pilgrims, many of whom would have come from Assisi, where the Portiuncula Indulgence was available on August 1st and 2nd.  This increased the friars' income, paving the way for the building of the present church. 

At about this time, Ubertino da Casale was summoned to appear before Benedict XI, having (in his own words) “borne witness to the truth” in a sermon in Perugia.  the people of Perugia interceded on his behalf, but his superiors sent him to the convent on Mount La Verna.  He was very much at home there, and and it was during his stay that he composed his seminal “Arbor Vitae Crucifixae Jesu” (The Tree of the Crucified Life of Jesus).

Brother Liberato, the leader of the zelanti who had taken refuge in Thessaly, decided to returned to Italy in ca. 1303 in order to make his peace with the papacy, leaving Brother Angelo behind to wind up the brothers’ affairs.  However, by the time that Liberato reached Perugia, Benedict IX lay dying.  He was buried in a monument that was originally erected in San Domenico Vecchio.  (It was moved to the left transept of the present church in 1700 and re-erected in its current location on the right wall of the apsidal  Cappella degli Apostoli in 1959). 

Brother Liberato decided to lie low in southern Italy until a new pope was elected, but he could not escape from persecution and he died there soon after.  Brother Angelo, now the leader of the dispersed zelanti, arrived at Perugia during the long papal conclave that followed the death of Benedict XI, and sought the protection of Cardinal Napoleone Orsini there.

Pope Clement V (1305-14)

The death of Benedict XI in Perugia in July 1304 was followed by a conclave there that was to elect his successor.  The main factions were balanced for almost a year before the “defection” of Cardinal Napoleone Orsini resulted in the election, in absentia, of the French Pope Clement V (in June 1305).  He resisted pleas to come to Rome, insisting first that Italy be pacified.  Thus began the period that became known as the Babylonian Captivity, during which the popes resided in Avignon.

Clement V appointed Cardinal Napoleone Orsini as Archpriest of St Peter’s, Rome in 1305.  He was also appointed as the papal legate to Tuscany, in order to pacify the strife-torn cities of Florence and Bologna in 1305.  Napoleone Orsini achieved very little in this respect, and returned to Avignon in 1309. 

In Spoleto, the Ghibellines under Abrunamonte da Chiavano expelled the Guelfs from the city in 1305, and they reassembled at Trevi.  They managed to re-enter the city a year later, reinforced by troops from Perugia and Gubbio.

War between Perugia and Foligno erupted again in 1305.  Perugia, with its ally Spoleto and the Guelf exiles from Foligno laid siege to that city for a month before it fell.  Corrado di Anastasio degli Anastasi was exiled to Todi and his brother, Bishop Ermanni degli Anastasi was transferred.  The Perugians installed the Rinaldo (Nallo) Trinci (1305-21) as Capitano del Popolo.  (This marked the start of the period of Trinci rule of Foligno that was to last until 1439.)  

St Clare of Montefalco

When Bentivenga da Gubbio, a Franciscan who had heretical views, tried to find converts among the nuns of Umbria in 1307, he made the mistake of trying to convert the future St Clare of Montefalco.  She appealed to Napoleone Orsini (in his capacity as papal legate and he arranged for his chaplain, Ubertino da Casale to mount a “sting” operation.  This produced the necessary evidence for the Inquisition, and Bentivenga was imprisoned for life.  

When St Clare died in 1308, Cardinals Giacomo Colonna and Napoleone Orsini soon arrived in Montefalco and initiated the process of canonisation under the direction of Berengar of Saint- Affrique, the vicar of the Bishop of Spoleto.  Berengar submitted the findings of the process to the Curia in Avignon in 1315.   Witnesses were then formally interviewed at San Francesco, Montefalco in 1318-9 and their depositions were submitted to a panel of three cardinals: Napoleone Orsini, Nicolò Albert da Prato and the Franciscan Vital du Four.  Their deliberations culminated in the “Relatio Trium Cardinalium”, which Napoleone Orsini wrote in 1328-32.  However, the process was suspended in 1333.  (The process was revived and again suspended in the 18th century and not completed until 1881).

Spiritual Franciscans

Clement V determined to resolve the dissension in the Order, which revolved around the issues of poverty and obedience and also the orthodoxy (or alleged lack of it) of the writings of Peter John Olivi .  He summoned Ubertino da Casale and his Franciscan opponents (who included Brothers Raymond de Fronsac and Bonagrazia di Bergamo) to Avignon in 1309 in an attempt to resolve their differences.  Ubertino contributed at least nine pamphlets to the debate, arguing the case for the separation of the Spirituals from the main Order.  The process continued during the Council of Vienne (1311) and culminated in the bull “Exivi de Paradiso” (1312).  This represented a compromise between the parties that Clement V hoped would avoid separation, but in fact it satisfied neither party.

Henry VII in Italy (1308-13, crowned 1312)

Henry of Luxembourg, who became the future Emperor Henry VII in 1308, was the first Holy Roman Emperor since the demise of the Hohenstauffen dynasty to show any interest in the affairs of Italy.  He gave unprecedented assurances of his good faith to Clement V in order to secure papal recognition.  He then left Germany for Italy in 1310 for his coronation in Rome, accompanied by three cardinals whom Clement sent for the purpose.

King Charles II of Naples had died a year before, and the leadership of the Guelf cause in Italy had passed to his son and successor, Robert of Anjou, King of Naples (1309-43).  Robert was wary but not initially overtly hostile to Henry’s approaches, but his Florentine allies were adamantly opposed to any accommodation with the Ghibellines.  They formed a Guelf League with Bologna, Lucca, Siena, and Perugia in 1310.  Inevitably, despite his desire for the reconciliation of the factions, Henry found himself allied with the Visconti of Milan against the Guelf delle Torre family, with Pisa and the other Ghibelline cities of Tuscany against Florence, and with the Ghibelline faction in Rome.

The Ghibellines of Umbria took heart from these developments.  The exiled Corrado di Anastasio of Foligno helped his allies at Spoleto to expel the Guelfs there in 1310, and from this base he threatened the Guelfs of Foligno.  The Ghibelline factions of Todi, Narni, Terni and Amelia also secured their cities.  The Perugians led the Guelf resistance in the region, forming an alliance with Orvieto, Gubbio, Lucca and Siena.  They were also able to call on levies from Città di Castello, Assisi, Foligno, Spello and Trevi, the last of which was the base of the exiled Spoletans. 

The Perugians appointed Gentile Orsini as their Captain General, and he acted first to secure the Spoletan Guelfs at Trevi.  However, he was not strong enough to enforce their re-entry into Spoleto, so he turned his attention on the contado of Todi.  He smashed a Ghibelline force led by Bindo dei Baschi at the Battle of Montemolino near Marsciano.  The Perugians then ravaged the contado of Spoleto and, in 1312, routed the Spoletan army as it tried to take Trevi, killing Abrunamonte da Chiavano.  The theatre of war then moved back to the contado of Todi, although neither side gained further obvious advantage.

Meanwhile, Henry of Luxembourg marched from Pisa to Rome in April 1312, determined that the cardinals would crown him there, despite the fact that the Pope had yet to give his specific approval.  By that time, John of Gravina, the brother of Robert of Anjou, and the Roman Guelfs held the city against him, aided by troops from the Guelf League (including 150 cavalry from Perugia).  Todi, Amelia, Narni and Spoleto sent levies to reinforce the imperial army.

Henry smashed his was into the city but was unable to reach St Peter’s because the Guelfs held the Castello di Sant’ Angelo.  His troops suffered a disastrous defeat in the streets of the city, and many, including the Umbrian levies, subsequently deserted.  However, the Guelfs were unable to press home their advantage, and the Ghibelline mob forced the reluctant cardinals to crown him as the Emperor Henry VII in the ruins of San Giovanni Laterano.  Henry then marched from Rome to Todi (August, 1312), where he raised troops from that city and from Spoleto with which to devastate the contado of Perugia.   After six days, he marched into Tuscany to besiege Florence, leaving the troops from Spoleto and Todi to continue the work.

In 1313, Orvieto became the theatre of war in Umbria, where the expected arrival of Henry VII encouraged the Ghibelline Filippeschi to intensify their war with the Guelf Monaldeschi within the city.  Each side received help from its Umbrian allies but eventually the Perugian aid to the Monaldeschi secured their victory.   The Filippeschi were exiled and never again constituted a political force within the city.

Henry VII died suddenly in 1313 and Clement V followed him to the grave in the following year.  This had a dramatic effect on the morale of the Ghibellines of Spoleto and Todi.  The opposing factions from Spoleto were reconciled in a ceremony at the foot of the campanile of San Lorenzo in Perugia in April 1314, while the factions of Todi were reconciled in August under the auspices of Perugia.

In 1313, Clemente V ordered Terni, Rieti and Todi to destroy the fortress of Miranda.  They laid siege to it, and it passed to the Church.

However, the death of Henry Henry VII did little to dampen the Ghibelline cause elsewhere in Italy.  To the north, the Ghibelline Matteo Visconti became Lord of Milan in 1313, while the Ghibelline Can Grande della Scala remained secure at nearby Verona.  Florence and the Tuscan Guelfs (including Perugia) suffered a military disaster at the hands of the Ghibelline Uguccione della Faggiola at the Battle of Montecatini (August 1315).  The papal legate, Bernardo de Coucy (whom the Italians called Bernard de Cucuiaco) provoked the Guelfs of the Patrimony (including Orvieto) into open revolt later in 1315, and had to turn to the Ghibelline Manfredi di Vico in order to reassert his position.

Pope John XXII (1316 - 34)

After a two-year papal vacancy, Pope John XXII was elected in 1316.   He had acted as Chancellor to Charles II of Naples and to his son and successor, Robert d’ Anjou in 1308-10.  He was thus prepared to place heavy reliance in Italy on the traditional Guelf alliance and in particular on Robert d' Anjou, whom he named as Governor of Rome.

The election of Louis of Bavaria as Emperor-elect in Germany in 1314 was contested.  John XXII maintained  that imperial prerogatives thus devolved to the papacy during what was, in effect, an imperial interregnum and appointed Robert d’ Anjou as imperial vicar for Italy in 1317.  He also sent Cardinal Bertrand du Poujet as his legate to northern Italy in 1319.

Lombardy and Tuscany

When Milan and Verona ignored his demand that they renounce imperial suzerainty in 1319, John XXII laid both under interdict.  He could not prevent the Ghibelline d' Este family regaining Ferrara in 1320, but he succeeded in splitting and weakening the Ghibelline powers in northern Italy. 

In Tuscany, the leading Ghibelline was Castruccio Castracani, Lord of Lucca, whose capture of Pistoia in 1325  posed a real threat to Florence.   Florence therefore launched a pre-emptive strike against  Lucca under its captain general, Ramòn de Cardona.   Castruccio Castracani fell back to defend Lucca and destroyed the Guelf army at the Battle of Altopascio: all that Bertrand du Poujet had achieved was now lost. 

After this defeat, Florence appointed Charles of Calabria, the son of King Robert d’ Anjou, its protector.  Lesser Tuscan cities, including Siena, soon followed.  In addition, in 1326, John XXII appointed Cardinal Giovanni Gaetano Orsini as a second papal legate to Italy.

Umbria

Robert d' Anjou had a small military base at Montefalco but was generally unable to exert much control in Umbria, which was threatened by three powerful Ghibelline leaders:

1. ✴Federico I da Montefeltro (1296-1322); and
   

2. ✴Bishop Guido Tarlati of Arezzo (died 1327) and his brother Pier Saccone.
   

The Perugians, who had lost men at the Battle of Montecatini, now perceived the threat nearer home.  They tried to form a Guelf league with Orvieto, Assisi, Spoleto, Gubbio, Foligno and other smaller Umbrian towns and cities, but the loyalty of a number of them was being undermined by internal dissent and by the overtures of the powerful Ghibelline centres.  

In September 1319, the Ghibelline Muzio di Francesco expelled the Guelfs with the help of Federico da Montefeltro.  He had himself elected as Capitano del Popolo, and Bishop Guido Tarlati sent Vanne da Poppi from Arezzo to act as Podestà.  In October 1319, Muzio di Francesco forced Bishop Teobaldo Pontano and the custodian of San Francesco to hand over papal tithes that had been collected in Assisi and Nocera.  In March 1320, he extorted the papal treasure deposited at San Francesco, warning  the reluctant friars that, were the treasure not released, the Perugians would take Assisi and steal the relics of St Francis.  Most of the stolen goods were sent to Arezzo to pay for military support. 

In November 1319, Abrunamonte da Chiavano expelled the Guelfs of Spoleto, aided by Muzio di Francesco and Federico da Montefeltro.  Many of the Guelfs who took refuge in the Duomo were slaughtered.   Some 400 Guelfs were imprisoned in the space under the Roman theatre, prior to their execution.  The houses of the defeated faction were looted, and many were torn down. 

The papal administration of the Duchy of Spoleto obviously needed a residence outside Spoleto at this time.  Jean d’ Amiel (Giovanni d’ Amelio, the treasurer of the Duchy of Spoleto in 1317-23 and rector in 1323-32) acquired a site outside Montefalco from the Bishop of Spoleto in order to build a new fortress (1322-4).  While it was in construction, the administration of the duchy was carried out from Foligno. 

In June 1320, Pope John XXII wrote to the rector of the Duchy of Spoleto, Reginaldo di Sant’ Artemia, and to Perugia, Orvieto, Foligno, Gubbio and other Guelf cities, pressing them to form a league against the Ghibellines of Assisi and Spoleto.  Perugian forces under Cante de’ Gabrielli besieged the town of Isola Romanesca (later called Bastia), in the contado of Assisi, for seven months, taking it in October 1320.  They stole the relics of the Blessed Conrad of Offida from the Franciscan church of Santa Croce there.  This army then regained control of Nocera Umbra in November 1320.

When Rinaldo Trinci died, his brother Ugolino I Trinci (1321-38), who was probably already in military service for Perugia, succeeded him as leader of the Guelf party of Foligno and Gonfaloniere di Giustzia.  By this time, Trevi, Bevagna, Spello and Montefalco acknowledged the suzerainty of Foligno.

In the summer of 1321, Federico da Montefeltro was named as captain of the forces of Spoleto.  He left Urbino in the hands of his son, Francesco and his cousin Speranzo, and moved to Spoleto.  John XXII excommunicated him (again) in August, and in December he ordered the Rector of the Duchy of Spoleto to preach a crusade against (inter alia) Spoleto, Urbino and Federico da Montefeltro.  When Pandolfo and Ferrandino Malatesta threatened Urbino, Federico da Montefeltro was forced to return there.  He faced a rebellion in April 1322, and presented himself to the crowd with a noose around his neck, begging for mercy.  Bishop Francesco Silvestri of Rimini incited the crowd to murder him, and he was buried as a heretic in the carcass of a horse.  (John XXII sent Francesco Silvestri a congratulatory letter in October).    

John XXII excommunicated Muzio di Francesco and placed Assisi under interdict in April 1321, by which time Perugian forces were besieging the city.  Muzio slipped away in August 1321 to take refuge in Todi.  Assisi now sent ambassadors to Perugia:they were offered lenient terms, but when Assisi rebelled again in March 1322, Perugian forces took the city, and this time the retribution was high.   Bishop Teobaldo Pontano initiated an inquisitorial process against Muzio di Francesco (who had been condemned as a heretic) in May 1322.  Muzio di Francesco faced the inquisition at San Fortunato Todi in June 1322, but that city ignored a subsequent order from John XXII that it should surrender him to the rector of the Duchy of Spoleto.  The inquisitors took some 90 depositions and compiled their report in August 1322.  

Spoleto, now without its major allies, withstood a siege by Perugian forces under Poncello Orsini and Ugolino Trinci for more than two years, before surrendering in April 1324.  The city became thereafter effectively a possession of Perugia, notwithstanding the protests of the papacy: Perugia imposed the right to appoint the podestà of Spoleto, and demanded an annual financial tribute.  They built a fortress in what is now Piazza Moretti.  John XXII found it expedient to formally approve these arrangements in 1325.  He was similarly unable to protect smaller cities in the Duchy of Spoleto (including Montefalco, Bevagna and Trevi) from exactions made by Perugia.

In 1323, a group of citizens of Città di Castello who were in rebellion against Brancaleone de' Guelfucci, the despotic head of the Guelf party, betrayed to city to Pier Saccone Tarlati, Rigone II del Monte and Gerio di Tano degli Ubaldini.  The Guelfs were driven out of the city.  After the defeat of the Ghibellines of Spoleto in 1324, Città di Castello became the centre of war in Umbria between the Guelfs led by Perugia and the Ghibellines.  Pope John XXII excommunicated Bishop Guido in 1324.  He died in September 1327, by which time both sides were exhausted.  In the peace that they negotiated, Città di Castello remained in the hands of Pier Saccone Tarlati and Gerio di Tano degli Ubaldini and his brothers.

[Jean d’ Amiel held a parliament in Foligno in 1324.]

Louis of Bavaria in Italy (1327-30, crowned 1328)

In 1322, Louis of Bavaria (the future Emperor Louis IV) emerged victorious after a disputed imperial election in Germany.  John XXII, who refused to confirm his election, excommunicated him in 1324.  In response, Louis of Bavaria published (at Sachsenhausen) an appeal in which he accused John XXII of heresy and appealed for a general council to adjudicate the dispute.

In June 1326, the process against Muzio di Fancesco, which had been suspended for some four years, was re-opened, as tension rose again in the expectation of the arrival of Louis of Bavaria in Italy .  Muzio di Francesco (who was probably serving in the army of Bishop Guido at Arezzo at this time) was given 30 days in which to present himself at San Gemini in the Duchy of Spoleto.  When he failed to do so, Bishop Teobaldo Pontano declared him in default, and re-opened the process in his absence.  Sentence against him was declared at San Fortunato, Todi in October 1326.  His goods in Assisi were confiscated, but he managed to evade capture.  (The last documentary reference to him dates to 1339, when he was at Fabriano.)

Louis of Bavaria duly entered Italy in 1327, intent upon coronation in Rome, heightening the tension between Guelfs and Ghibellines.   At the request of Perugia, Jean d’ Amiel, the Rector of the Duchy of Spoleto, held a parliament in order to organise the defence of the region.  John XXII sent letters to Perugia, Orvieto, Florence and Siena formally requesting their assistance.

John XXII advised Jean d’ Amiel to move his base to Gualdo Tadino in order to secure communications between the Duchy of Spoleto and the March of Ancona.  He subsequently approved the confiscation of the Abbazia di Sant’ Eutizio, which was heavily fortified and thus provided him with an alternative base for this purpose.  Abbot Margarito travelled to Avignon and apparently persuaded John XXII to reverse the decision, but the abbey nevertheless remained in the control of the secular authorities.  

Louis of Bavaria was largely unopposed as he followed the route that Henry VII had taken to Rome.  In Umbria, Narni, Todi and Amelia openly openly declared their support for him.  The Romans invited him into the city and the Ghibelline Cardinal Sciarra Colonna duly crowned him (January 1328).  Louis IV sent an army to march on Orvieto but it was recalled to suppress a revolt in Rome (March 1328).

Jean d’ Amiel restored part of the walls of Montefalco, near Porta di Sant’ Agostino in 1328.

Louis IV raised concerns even among his own supporters when he created a Franciscan, Peter of Corbara as the anti-Pope Nicholas V (May 1328).  John XXII declared a crusade against them, and Louis IV was forced to withdraw from Rome (August 1328).  When the welcome promised by the Filippeschi family at Orvieto was not forthcoming, he availed himself of the of the Chiaravallesi at Todi.  The friars of San Fortunato joined in the welcome, and Nicholas V installed himself in their convent.  His army ravaged the contadi of Bevagna and Foligno.  He finally left Todi at the end of August, leaving the city despoiled and violated.

Louis IV failed to establish a solid base in Italy, and returned to Germany in 1330, leaving only increased confusion in his wake.  Perhaps wisely, the Milanese sought reconciliation with John XXII, who duly named Azzo Visconti imperial vicar of Milan in 1330. 

John of Bohemia

In 1328, John of Bohemia, the son of the Emperor Henry VII invaded Lombardy, where he proposed to establish a kingdom that he would hold as a papal fief.  John XXII supported him, thereby losing the support of Robert d’ Anjou and of Florence.  Florence joined the Visconti and Este families in the anti-papal League of Ferrara (1332), to which Robert d’ Anjou gave tacit support.

The forces of the league defeated John of Bohemia and the papal legate, Bertrand du Poujet outside Ferrara in 1334.  John of Bohemia then left Italy, and the papal stronghold of Bologna was lost.  John XXII died shortly thereafter.

Michael of Cesena

Michael of Cesena was elected as Minister General of the Franciscans during the chapter of Naples (1316).

A dispute between John XXII and the mainstream of the Franciscan Order erupted [when?] at Narbonne when a an alleged heretic who insisted  that Christ and the apostles had held no possessions, either individually or in common was burned at the stake.  The Franciscans in Narbonne defended the heretic’s view, and the matter was referred to John XXII.  He linked the issue to what he regarded as the fiction that the Franciscans similarly owned nothing.  

Following the General Chapter at Perugia (1322), the Franciscans sent a letter to John XXII, requesting him to uphold the prohibitions on further debate of Franciscan poverty that was contained in “Exiit qui seminat” (1279).  Michael of Cesena , together with all the ministers and masters present at the chapter, published a declaration in which they affirmed the Franciscan view that: “Christ and the apostles had possessed nothing, either individually or in common”.  They declared this doctrine was not heretical, “but healthy, catholic and faithful, above all because the Holy Roman Church expressly upheld, affirmed and determined it.”

John XXII answered with the bull “Ad conditorum canonum” (1322).  In this, he drew on the views of Thomas Aquinas, whom he canonised in 1323.  When Brother Bonagrazia of Bergamo published a written appeal, John XXII arrested and imprisoned him.  He then republished “Ad conditorum canonum”with only slight modification.  In it, he declared that henceforth the Church would only accept ownership of items used by the Franciscans in relation to their churches, oratories and buildings, and of their books, sacred vessels and vestments that were destined for the divine offices.  In “ Cum inter nonnullos” (1323), he declared heretical the affirmation that Christ and the apostles had possessed nothing, either individually or in common.  This implied that the Franciscan Order: (a) could not claim to follow apostolic poverty; and (b) was guilty of heresy.

John XXII summoned Michael of Cesena to Avignon in 1327.  He was not allowed to attend the Franciscan General Chapter that was held in 1328 in Bologna, but the delegates who did attend refused to obey the papal instruction that he should be deposed.  Michael of Cesena, Bonagratia of Bergamo and William of Ockham fled from Avignon and took refuge in the court of Louis IV at Pisa.  John XXII duly excommunicated them as heretics, and formally removed Michael of Cesena from office.  In 1329, he convoked a general chapter, in which Brother Gerald Odonis was elected.  Michael of Cesena fled to Munich, where he died in 1342.

Spiritual Franciscans

Pope John XXII finally condemned the Celestines in 1317.  The body of the leading Franciscan Spiritual, Peter John Olivi was removed from the tomb in 1318, and his cult was suppressed.

Ubertino da Casale was able to remain at Avignon for a considerable period, under the protection of Cardinal Orsini and Cardinal Giacomo Colonna.  He was estranged from the local Franciscans, and John XXII instructed him to transfer to the Benedictine Order.  He retained the good opinion of John XXII until 1324, when he was accused of heresy and fled. He probably joined the cause of the Emperor Louis of Bavaria in Italy, and died in ca. 1330.

Angelo Clareno composed his “Chronicon seu Historia Septem Tribulationum Ordinis Fratrum Minorum” (The Chronicle or History of the Seven Tribulations of the Order of Friars Minor) in 1325-1330, at the Benedictine monastery of Subiaco.  He died in 1337.

Anarchy in Tuscany and Umbria

When John XXII died in 1334, his successor Pope Benedict XII decided that military efforts to preserve the temporal power in Italy were a waste of money.  He refrained from sending powerful legates, and tried instead to run his Italian policy from Avignon.  As a result, any residual papal control in Umbria disintegrated. 

Ermanno Monaldeschi became lord of Orvieto after his coup of 1332 against other branches of his family.  (As part of this manoeuvre, he signed away Chiusi to Perugia).

Pier Saccone of Arezzo still controlled Città di Castello, much to the irritation of Perugia.  War between them erupted again when Pier Saccone attacked the Perugian possession of Cagli in the Appenines in 1335.  His many enemies, who included both Guelfs and Ghibellines, supported Perugia, which had an early success when it took Borgo San Sepolcro in 1335.  The Florentines now entered the war as allies of Perugia, and the two armies besieged Arezzo.  However, the Florentines betrayed the Perugians by purchasing Arezzo in 1339.  For Perugia, the consolation prize came in the form of Città di Castello, which granted the Perugians the right to elect the Podestà and Capitano di Popolo and gave them custody of the citadel and the keys of the city for twenty years.

Pope Benedict XII sent Jean d’ Amiel back to the duchy in 1339-40 with special powers to deal with abuse by other papal officials in the duchy.

Perugia now suffered a series of setbacks.  First, the Florentine constitution collapsed in 1342 under the strain of economic depression.  The Florentines turned to the widely distrusted Walter of Brienne, who made peace with Ghibelline Pisa.  Other Ghibellines, including Pier Saccone hastened to acknowledge him as their feudal lord and Perugia was now on the defensive.  Pisa had just dispensed with the services of the Great Company, under Werner (Guarnieri) of Urslingen, and he was not slow to move against Perugia in its weakened state.  He ravaged its contado and that of Città di Castello in 1342.  Perugia refused to pay the huge bribe he demanded, and instead employed Guido Orsini to contain his forces and to shepherd them out of its territory. 

A further blow came in 1343 when Robert d' Anjou died, leaving Perugia alone as the leader of the Guelf cause in central Italy.  The Florentines expelled Walter of Brienne soon after, starting a chain of events that led to war.  Arezzo expelled the Florentine garrison, and Pier Saccone used this opportunity to besiege the city.  He also occupied Castiglione Aretino (modern Castiglione Fiorentino) and nearby Citerna, which had fallen to Perugia as part of the earlier settlement.  The Perugians were now intent upon his destruction, and formed an alliance with Arezzo, Florence and Siena for the purpose.  They were also able to command levies from Assisi, Spello, Foligno, Spoleto, Bettona, Nocera, Gubbio, Gualdo Tadino and Città di Castello.  In 1345, Pier Saccone was forced to restore Castiglione Aretino and Citerna to Perugia.

Perugia's next problem occurred at Orvieto, which had been in the grip of political turmoil ever since the coup of Ermanno Monaldeschi in 1332 as the Monaldeschi clan fragmented.  In 1346, the Sienese helped the Ghibelline Beffatti faction to take power.  Perugia was able to reinstate the Guelf Benedetto di Bonconte but he was, in his turn, overthrown by Corrado Mondaleschi, aided by Giovanni di Vico, the Ghibelline Prefect of Rome and Lord of Viterbo. 

Pope Clement VI urged Perugia to intervene once more, but he received a frosty response on this occasion.  Just weeks before, he had declared that Perugia was directly subject to the papacy, ignoring the Commune's historic privileges.   However, Cola di Rienzo, the self-styled and short-lived Tribune of Rome (1347-8) happily obliged the Pope, and for a time the ambitions of Giovanni di Vico were contained. 

Unfortunately, those of Cola di Rienzo were not.  He offered protection to the communes of the Papal State from both papal legates and home-grown despots, and many of them voluntarily acknowledged his suzerainty.  Clement VII made preparations to oppose him, but these proved unnecessary when the Romans who had so recently rallied to him now expelled him from the city. 

Another threat now loomed in the person of the condottiere Werner (Guarnieri) von Urslingen and his “Great Company”.  He ravaged the Papal States (including the contado of Narni) for some three months in 1348.  The sack of Anagni was particularly terrible, and this seems to have been the event that prompted Orvieto to seek the suzerainty of Perugia for a period of ten years.  Soon after, the Black Death wrought its devastation, followed in 1349 by a major earthquake in central Italy.  The Jubilee Year of 1350 brought some limited respite, but there is no doubt that the fabric of communal government had been seriously undermined.