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Sigismondo Pandolfo Malatesta, second son of Pandolfo III of Fano, is born as Gismondo Malatesta, the scion of a family who had ruled Rimini since 1295. He has two brothers: Galeotto Roberto (1411-1432) and Domenico, also called Malatesta Novello (1418-1465). All the three sons of Pandolfo are illegitimate.

Pope Martin V 1417-1431


The daughter of Carlo Malatesta, and Sigismondo’s cousin, Parisina, is married to Niccolò d’Este III, Marquis of Ferrara. She will have two daughters by him. The elder, Ginevra (1419-1440), will become Sigismondo’s first wife in 1434. See Genealogy of the Malatesta.


Parisina is discovered of having an affair with her husband’s son, Ugo, and Niccolò has them both beheaded. Pound refers to this misfortune in canto VIII: “And, Este’s house, Parisina/ Paid/ For this tribe paid always (VIII 163-65).


Pandolfo III dies before legitimizing his three sons. His brother Carlo takes over Rimini and continues the struggle for legitimation. The eldest son, Galeotto, is declared legitimate by virtue of his piety.


Sigismondo's uncle, Carlo, dies and Pope Martin V tries to take control of Rimini on the pretext that Carlo has not paid the levies due to the Church. Sigismondo succeeds in dispersing the papal troops, though he is just 13 at the time.

Galeotto becomes Lord of Rimini and rules until his death in 1432.


Sigismondo succeeds his elder brother as Lord of Rimini and is recognized by the Pope. He takes over lands south of the Marecchia, which flows into the sea at Rimini, whereas his brother, Domenico, will rule over the region north of the river, with Cesena as his capital.

Pope Eugene IV 1431-1447


The Holy Roman Emperor, Sigismund, is formally crowned by the Pope. On returning north from Rome, he passes through Rimini and knights Gismondo and Domenico. At the time, Gismondo is 16. This event is crucial to his self-image: in honor of his patron, he will change his name to Sigismondo and have the emblem SI carved in the walls of the Tempio Malatestiano.


The Byzantine Emperor John Paleologus (r. 1425-1448) is trying to enlist the help of the Italian princes against the impending threat of the Ottomans by agreeing to heal the rift between the Eastern and Western Churches. He comes to Italy together with his theologians and the Neoplatonist philosopher Gemisthus Plethon to participate in the Council of Ferrara. But since Ferrara has the plague, the council is held in Florence. The meeting between Pope Eugenius IV and the Patriarch of Constantinople leads to a political agreement which causes great indignation at Constantinople; it is not ratified, therefore the alliance and military aid are not forthcoming when the Ottomans finally conquer the city in May 1453.


Sigismondo is appointed chief commander of the papal forces.


Sigismondo’s first wife, Ginevra, dies.


Bianca Visconti, the natural daughter of the Duke of Milan, marries Francesco Sforza, a peasant turned condottiere.

Sigismondo's natural son Roberto is born. His mother is Vanetta dei Toschi of Fano. Roberto would be made legitimate in 1450 and inherit Rimini in 1470.


April - Sigismondo marries Polissena, Francesco Sforza’s daughter.


May - Bianca Visconti and Francesco visit Rimini on the way to the battle of Ancona and are received with great festivities. These are described in Canto VIII: 99-115.

Sigismondo allies himself with Sforza to fight the latter’s enemies. The understanding is that Sforza will aid him gain Pesaro from his cousin, Galeazzo Malatesta the Inept.


15 January - Galeazzo the Inept, Lord of Pesaro, sells the city to Francesco Sforza for 20,000 florins. His brother, Alessandro Sforza, becomes Lord of Pesaro.

Galeazzo also sells Fossombrone to Federigo d’Urbino. The sale is completed in 1445 and in March, the new masters take over (IX: 29-45).
Pound’s source, Gaspare Broglio, gives 16 March 1444 as the date of the contract.


Sigismondo is invited to Rome, received with full papal honors, and awarded the Sword and Hat of the Holy See.


Pisanello makes his two medals of Sigismondo.

1447 -1448

The Duke of Milan, Filippo Maria Visconti, dies without male issue, an event which starts a long war for the Milanese succession. Several powers try to claim Milan: Venice, which attempts to extend its territory in the “terra ferma”; The King of Naples, Alfonso de Aragon, who claims that Visconti has promised him the succession; the city, which proclaims itself a republic; and Francesco Sforza, who will finally succeed in taking over the city and install himself Duke in 1450.


Sigismondo is hired by Alfonso to defend his claim, but he breaks his agreement in order to sign up with Alfonso's enemy Florence, which is the ally of Venice. As commander of the Florentine troops, he is able to successfully resist Alfonso’s siege of Piombino (September 1448) and scores a valuable victory for the Florentine cause (Jones 200). At the same time, he refuses to return the 27,000 ducats received from Alfonso for troops and equipment (IX: 46-56).

This betrayal (or “change-over,” as Pound calls it in Canto IX) is considered by many historians to be Sigismondo's supreme political error, since it excludes him from the peace at Lodi in 1454 and generates a war with Naples ten years later (Jones 198-99; Lavin 345).

Pope Nicholas V 1447-1455


Sigismondo is besieging Cremona, a city owned by Bianca Visconti, who has received it from her father as dowry. He is in the pay of the Venetians, because the Florentines have conceded his services to their allies. This is why in March and April 1449, he still reports his military provision to Giovanni de Medici (VIII 4-56; 90-98).


Isotta’s son by Sigismondo, Malatesta de Malatestis, is born.


Francesco Sforza becomes the Duke of Milan and succeeds in founding a ducal dynasty.

Francesco Sforza and Federico di Urbino plot to sever Sigismondo’s condotta (military service) with the Venetians. Federico tricks Malatesta into believing that he will get his help in reconquering Pesaro. The plot is successful. Sigismondo breaks his service with the Venetians and comes to Pesaro to find himself cheated: Federico announces that he is coming to aid the defense of the city, not its siege (IX: 64-79; 96-104).


A German lady coming to Italy for the Jubilee year is attacked and raped. Venice is particularly sensitive to this event, since the attack happens in their lands, near Verona. Sigismondo is under accusation, but protests that this is a calumny. As there is no agreement as to time, place, and perpetrator, the pope does not accuse Malatesta (Jones 202-3). See IX: 93.

Sigismondo consecrates the Tempio.

31 August. Pope Nicholas legitimates Sigismondo’s two sons, Roberto and Sallustio (born of Vanetta dei Toschi) (Jones 204).


29 May - Constantinople falls to the Ottomans.

Sigismondo scores a second victory for Florence and against the Aragonese by successfully laying siege to Vada. This victory is praised by Basinio and Valturio.


“Cosimo [de Medici] was the principal architect of an alliance with the Sforza of Milan that culminated in the Peace of Lodi (1454). By this pact Milan, Florence, Venice, and (in 1455) King Alfonso of Naples and Pope Nicholas V bound themselves together in an “Italian League” against any power, Italian or foreign, that should disturb the existing balance. At the same time, the treaty established special machinery for the peaceful settlement of any disputes that might arise among the states. Despite some local conflicts, the creation of the Italian League brought about a much more peaceful era in the second half of the century. Peace was assisted, above all, by a general exhaustion among most of the major powers, whose economies and societies could no longer support the strains imposed upon them by wars.” (Encyclopaedia Britannica online)


At the instigation of Alfonso de Aragon, Sigismondo is excluded from the peace at Lodi, which means that his lands are not protected by the treaty against invasion. Alfonso reserves the right to make war on him, which he proceeds to do in November 1457.


October - The Sienese are engaged in a war with Aldobrandino Orsini, Count of Pitigliano. They hire Sigismondo to lay siege to the fortress of Sorano. At the end of the year, Sigismondo decides to lift the siege and the Sienese, persuaded that he has betrayed them, raid his camp and seize his postbag (IX 114-153; X 1-31).


The work at the Tempio is interrupted, leaving the front unfinished and the roof not even begun.

Pope Calixtus III 1455-1458



Sigismondo marries Isotta.


May – secret agreement between Sigismondo and Jean d’Anjou for help in the impending war with Urbino and Naples.


May - Sigismondo and Federico da Montefeltro meet at Borso d’Este’s country retreat Belfiore (Jones 215). It is a last attempt at reconciliation before war (X: 36-44).


Federico allies himself with the King of Naples and Piccinino to attack Sigismondo. Malatesta Novello declares himself neutral. Federico wants back fortresses which Sigismondo had conquered; Piccinino wants a state; Alfonso wants his money back and extra “expenses” [27,000 + 70,000 ducats] (Jones n.2 219).


November - Alfonso invades Sigismondo’s lands because of the grievances of 1447. His troops are under the command of Giacomo Piccinino. As Sigismondo has been excluded from the peace at Lodi, his domains are not protected by the treaty (Pius Commentaries II:32).



27 June - Alfonso of Aragon dies. His son, Ferdinando now continues the war against Rimini and demands of the pope that Piccinino should have a state of his own at Sigismondo's expense.


The new pope, Pius II, is friendly to the House of Aragon. In order to get Piccinino out of Assisi, which the condottiere had recently occupied, he promises Ferdinando that in the event of a peace between Naples and Malatesta, Piccinino will receive compensation, i.e. land in Sigismondo’s territory.

Pope Pius II 1458-1464


April – first meeting at Florence. The pope does not evaluate the claims of Naples, but tells Malatesta to pay up: “No matter what you say in your own defense, everyone believes you betrayed Alfonso. Your infamous behavior both provides the charge against you and demands the sentence” (Commentaries Book II: ch. 32). Sigismondo refuses indignantly.

Piccinino, re-established in Naples’ pay, resumes his attack on Sigismondo’s lands.


June –August – meeting at Mantua.

Pius II’s peace conditions: Sigismondo shall:

  • pay Naples 50,000-60.000 ducats within the year.
  • restore to Federico da Urbino the castles he had taken in the Montefeltro.
  • give Pius the vicariates of Montemarciano, Mondavio and Senigallia, as security for repayment of the debt to Naples (Commentaries Book III: ch. 24).

Summer – in Naples, the prince of Taranto and other nobles of Sicily rebel against Ferdinand of Naples.


September - Attempt by Sigismondo to abide by the Mantua terms. Castles are surrendered to the pope as pledges; others are returned to Federico da Urbino.


October – November – Jean d’Anjou launches his offensive on the coast of Naples.

Piccinino’s interests have not been taken into account by the Mantua treaty - he refuses to withdraw from Malatesta’s lands, conquering even more.


January – Piccinino and his army is allowed by Malatesta Novello to winter in Cesena. Sigismondo and Piccinino agree that in return for his lands, Sigismondo will allow Piccinino free pass to advance against Naples. Three weeks later, Piccinino comes to terms with the Angevin and in March he takes his army south against his former patron.

July – September – Sigismondo enters into an agreement with the Angevins. This stipulates aid in money and troops to reconquer his territories and move into Pesaro and Urbino. He is to accept no service with king, pope, or duke; keep up hostilities in the papal states; and invade Naples when summoned.


Sigismondo expels the papal forces from Montemarciano. This sets off a war with the pope, with Naples, and with Federico da Montefeltro. Sigismondo is in alliance with the House of Anjou, the Prince of Taranto, and Piccinino.


15 October – the pope commands Sigismondo to remit the census of 10,000 ducats owed over the four past years. Sigismondo ignores this.

Sigismondo attacks and takes another fortress pledged to the pope, Mondavio.


December – the Malatesta brothers are excommunicated.


16 January - in a public consistory, Andreas Benzi delivers an oration full of calumny against Sigismondo which is received with no word of criticism or protest (X: 65-97).


A more formal indictment is prepared by Nicolaus Cusanus, Cardinal of Vincoli, which should allow Sigismondo to respond. He is summoned to Rome to defend himself. Sigismondo ignores this.

April – a new excommunication of Sigismondo.


July – Malatesta scores a victory against the pope at Nidastore (X: 151-56; XI: 1-28). He attempts a peace treaty only to find the pope inflexible on every issue.


14 October - In a private consistory, Nicolaus Cusanus reinforces Benzi’s points. The appropriate witnesses ("testibus idoneis") are Sigismondo’s enemies, Federico da Urbino and Alessandro Sforza (X: 106-111).


27 April – Nicolaus Cusanus reads the indictment against Sigismondo publicly. In various places in Rome, he is burned in effigy (X: 55-60; 111-117).

Sigismondo is deprived of his vicariates in Rimini, Fano, Senigallia, Montefeltro, Cesena, and Mondavio.


12 August – Sigismondo conquers Senigallia only to be faced by Federico at the head of papal forces. He is defeated.


18 August - Piccinino and the Angevin alliance is crushed at Troia. The papal army takes control of Sigismondo’s lands.


late August - Sigismondo travels to Taranto to try and save what is left of the Angevin alliance, but his allies feel defeated.

Sigismondo decides to sail north to Venice to ask for help. A storm from which he barely escapes with his life blows him on the Dalmatian coast. He manages to arrive in Venice at the end of October (Jones 234). Pound refers to this shipwreck in canto XVII.

October – Venice and Milan decide to intervene and press for peace. On 12 October, the Venetian diplomat Niccoló Segundino is tasked with securing peace for Malatesta.

On 28 October, the Senato Secreto has a meeting discussing armed help for Malatesta Novello in Cesena. Another mission to Rome, that of Bernardo Giustiniani, intervenes on the Malatestas' behalf. Pound refers to these missions in canto XXVI.

The pope accepts to leave Malatesta Novello out of the conflict but refuses to soften on Sigismondo.


April - Malatesta Novello sells Cervia and its salt mines to the Venetians by a secret treaty.


Tivoli, 26 August – Malatesta Novello surrenders Cesena. He is allowed to remain in the city until his death, and after that date, the city will revert to the pope. Sigismondo is now alone (Jones 237).


25 September – the city of Fano, defended by Roberto Malatesta, Sigismondo's eldest son, falls to the papal army.


Neither Sigismondo nor Malatesta Novello have any military forces left and hope only in the intercession of the Italian powers, especially Venice and Milan. Venice makes the peace with the Malatesta a condition of its participation in the pope’s planned expedition against the Ottoman Empire.


October – peace is finally granted. Conditions:

  • All territories but Rimini and a small suburb are to be given up. And these Sigismondo is allowed to keep for his lifetime at a census of 1000 florins a year.
  • Sigismondo is to sue for pardon, acknowledge a heretical conduct, and receive formal absolution.


Spoils are distributed among the victors, mostly to Federico da Montefeltro and the Pope’s nephew, Antonio Piccolomini. Alessandro Sforza receives Gradara and Castel Nuovo.


Spring - The Venetians send a military expedition to Peloponnesus (Morea) under Sigismondo’s command to counter the Turkish invasion. Morea at the time was for most part a Venetian territory. The expedition fails, but Malatesta brings back the bones of Gemisthus Plethon to Rimini and puts them in one of the sarcophagi flanking the Tempio.


1465 – Piccinino marries Drusiana, Francesco Sforza’s daughter. A few weeks later, he is "invited to lunch" in Naples and assassinated.


November 1465 – Malatesta Novello dies in Cesena. The town reverts to the pope.

Pope Paul II 1464-1471


14 April - Sigismondo is permitted to return to Rimini (Yriarte 294).

23 April 1466 - Sigismondo makes his testament and excludes Roberto from it.

May 1466 - Pope Paul II awards Sigismondo the Golden Rose for his service in the Morea (Yriarte 295).

Sigismondo hopes that Paul will return a few lands lost in 1463, because of his service against the Ottomans. On his first meeting with the pope, he achieves nothing. Paul demands that the Venetian troops stationed in Rimini during Sigismondo's absence are withdrawn.

1467 - Sigismondo learns that the pope wants to dislocate him from Rimini, in exchange for a lesser domain like Spoleto and Foligno. On hearing this, Sigismondo is frantic and plans to murder Paul. The pope receives him in the presence of seven cardinals and denies the plan to dispossess him. He offers to make him condottiere for the papal army and this service continues until Sigismondo's death a year later (Jones 243-44). 



Spring – during a campaign against Norcia on behalf of the pope, Sigismondo falls ill.


October - Sigismondo dies at 51.




Jones P. J. 1974. The Malatesta of Rimini and the Papal State. Cambridge: Cambridge UP, 2005.

"Lodi peace.” Encyclopaedia Britannica online.

Pius II. Commentaries. Ed. Margaret Meserve. 2 vols. [Books I-IV.] Cambridge Mass.: Harvard 2004.

Yriarte, Charles. Un Condottiere au XVe siècle. Paris: Rothschild, 1882.


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