Ludovico Orsini: The Condottiere Who Set Fire to Rome After a Pope's Death

The Count of Pitigliano Who Fought Siena for Three Decades

Count of Pitigliano and Anguillara. Lord of Sovana, Morlupo, Fiano Romano. Son of Niccolò Orsini, brother of Chiappino Orsini, father of Giovan Francesco Orsini, father-in-law of Gian Giacomo dei Medici, of Federico Gonzaga da Bozzolo and of Luca Savelli. Son-in-law of the lord of Siena, Pandolfo Petrucci.

1534 (January)

Year, Month	State, Comp. ventura	Opponent	Command	Area of Activity	Actions Undertaken and Other Salient Facts
1491
Oct.	Church	Ascoli Piceno, Naples		Marche	Supports his father Niccolò in the war against Ascoli Piceno and the Aragonese. Assists his relative at Ripatransone.
1493
Nov.				Toscana	Receives Pope Alexander VI at his castle in Pitigliano.
1495
June				Umbria	Escorts the pontiff to Perugia with Bartolomeo d’Alviano.
1496
Jan.	Siena	Exiles		Toscana	Takes part in the defense of Siena, threatened by the exiles.
Nov.	Siena		30 lances	Toscana	Is obligated to have his company reviewed three times a year.
1498
Sept.	Siena				His condotta is renewed under pressure from the lord of Siena, Pandolfo Petrucci.
1499
Aug.					Is granted a condotta of 100 lances by the Venetians. This is soon changed into an annual provision of 2,000 ducats.
1500
	Venice	Sforza	100 lances	Lombardy
May					At Ghedi, his father’s lordship. Escorts to Brescia with his company Cardinal Ascanio Sforza, captured by the Venetians, who is to be handed over to the French allies.
June	Venice	Ottoman Empire		Lombardy and Friuli	With his father Niccolò in Friuli to deal with possible Turkish raids in the region.
1502
Sept.	Pitigliano	Church		Toscana	The Venetians intervene in his favor and defend him from the threats of Pope Alexander VI.
1503
Jan.				Toscana	Hosts at Pitigliano Guidobaldo da Montefeltro, Giulio Vitelli, Fabio Orsini, Giovanni di Ceri, Giovan Corrado Orsini, Franciotto Orsini and Giulio Orsini, all persecuted by the papal forces.
Feb.				Toscana	Leaves Pitigliano. Unsuccessfully attempts to enter Siena.
Aug.-Sept.				Lazio	On the death of Pope Alexander VI, bursts into Rome through the Porta di San Pancrazio with Fabio Orsini at the head of 400 horsemen and 500 infantry; Cesare Borgia shuts himself in the Vatican. Orsini forces his way into the Spanish quarter of the Banchi and sets fire to some houses and warehouses belonging to merchants and courtiers. He stops at Monte Giordano; he has gallows erected in front of the palace where he is lodged so that the disorders will end. Following the agreement between Prospero Colonna and Duke Valentino, he must leave the city at the urging of the college of cardinals. He moves to Mentana.
Oct.	Spain	France	30 lances	Lazio	The new pope Pius III declares in favor of Cesare Borgia; Ludovico Orsini enters the pay of the Spanish to fight the French, who protect Borgia.
Dec.				Campania	Is present at the Battle of Garigliano.
1505
Aug.	Florence	Company of adventure	60 lances	Toscana	Consalvo di Cordoba forbids him to follow Bartolomeo d’Alviano in his expedition against the Florentines, aimed at favoring the Medici and the Pisans. He then serves Florence; he contributes to the victory of Campiglia Marittima over Alviano himself. At the end of the month passes through Castelfiorentino with his company with the aim of attacking Pisa.
Sept.	Florence	Pisa		Toscana	Takes part in the second assault on the walls of Pisa after the artillery has knocked down 45 metres of the city walls near the Barbagianni tower. He is to be supported in the attack by the infantry of Piero del Monte at Santa Maria. The soldiers refuse to move; nonetheless Ludovico Orsini enters the breach with Piero del Monte at Santa Maria, followed by a few infantrymen; he is wounded in a foot by a musket shot.
1508
Apr.	Florence	Pisa		Toscana	With Marcantonio Colonna, he has 12 Florentine infantrymen pretend to desert to the Pisans in order to gain an opportunity to infiltrate the enemy camp: they make contact with Tarlatino Tarlati. Discovered, 6 of them escape to safety and 6 are hanged.
1510
Mar.				Toscana	At Pitigliano, for the solemn funeral rites given to his father Niccolò.
1511
				Umbria	Is appointed among the conservators of Orvieto.
Oct.				Toscana	With Guido da Castell’ottieri renews the pact of alliance with the Sienese.
1512
	Exiles	Siena		Toscana	Assists Borghese Petrucci in his attempt to return to Siena.
Dec.				Romagna	Is reported at Forlì.
1513
Jan.				Romagna	Still in Romagna, at Faenza.
Mar.				Lazio	In Rome for the coronation of Pope Leo X.
May					Is again elected among the conservators of Orvieto. Does not accept the position.
June	Exiles	Siena		Toscana	Moves to Monte San Savino with Troilo Savelli. Is urged by the Sienese exiles to intervene in Siena to strip Borghese Petrucci of the lordship of the city. Pope Leo X restrains the two condottieri.
Aug.	Florence		50 lances	Toscana	In Florence for the review of his men. In a ceremony hands over to Lorenzo de’ Medici the standard and baton of captain general.
1515
July	Florence	France, Venice	70 lances	Lombardy	Is sent into the Duchy of Milan to support the imperial and ducal forces against the French and Venetians; his task is to facilitate the flow of supplies to the allies. He is reported at Lodi and at Monza.
Aug.			74 lances	Emilia and Lombardy	Arrives in the area of Piacenza. With Rinieri della Sassetta, Guido Rangoni, Niccolò da Bagno, Ludovico Euffreducci and Rinaldo Zatti, he is tasked with escorting to Lodi the Cardinal of Sion, Matthäus Schiner (Matteo Scheiner), who commands the Swiss militia. Since the Viceroy of Naples Raimondo di Cardona does not link up with the allies, Orsini moves to Stradella.
					Renews with the Sienese the existing treaty of accomandigia (protection).
1517
Jan.	Florence	Company of adventure		Umbria	Opposes Francesco Maria della Rovere, who aims to reconquer the duchy of Urbino. Joins the defense of Perugia.
Feb.				Lazio	Goes to Viterbo to sign, on behalf of the Gattesca faction, a peace treaty with the supporters of the opposing Maganzese party.
1520
Nov.					Is approached by the French to enter their pay.
1521
	Church	France, Venice	50 lances
Sept.				Emilia	Moves along the Enza with Baldassarre Castiglione at the head of 100 lances.
Dec.				Lazio	On the death of Pope Leo X, the college of cardinals entrusts him with the command of a number of Italian infantry to oversee the proper conduct of the conclave.
1522
Mar.	Florence	Company of adventure		Toscana	Joins the defense of Rapolano Terme when Renzo di Ceri invades Sienese territory.
1523	Siena		Captain general	Toscana
1525
Feb.	France	Empire	50 light cavalry	Lazio	Arrives at Monte Guardia with 50 light cavalry, ready to join the forces of Ceri and the Duke of Albany, whose objective is to invade the Kingdom of Naples.
Nov.-Dec.				Lazio	Assists Galeazzo Farnese in recovering Castel di Piero (San Michele in Teverina) from Pirro Colonna.
1526
June-July	Church, Florence	Colonna, Siena		Toscana	Is mandated, together with his son Giovan Francesco, to raise 150 men-at-arms and many infantry to counter possible attacks by the Colonna family. Moves against Siena to retake Sovana, an ancient fief of his family, with Virginio Orsini, Gentile Baglioni and Giovanni da Sassatello. Gathers the militia at the bridge of Centina, crosses the Arbia and continues along the Roman road toward Montalcino. The inhabitants refuse to supply the troops; Orsini decides to assault the walls of the town. The inhabitants defend themselves vigorously and kill 100 papal soldiers; they are about to give way when Sallustio da Roma comes to their aid. Forced to withdraw, Orsini heads for Siena with 1,200 cavalry, 8,000 makeshift infantry and seventeen pieces of artillery. Divisions among the various captains and the exiles render the siege operations ineffective. The troops are encamped in a suburb with no way out on the flanks; the only exit is blocked by the stalls of the sutlers, so the space available for the exit is only fifteen feet. Disorder in the camp is such that Pope Clement VII orders the militia to withdraw the artillery and abandon the siege. 400 infantry come out of the Porta Camollia and attack the moving convoy of artillery escorted by Corsican infantry. These flee; when the sutlers see the Sienese coming at them, they try to gather their belongings, occupying every available space for those fleeing. The confusion increases; the victory of the Sienese is complete. Ten Florentine cannons and seven Perugian cannons are left on the field, all carried in triumph to Siena along with the wagons. The Florentines take refuge in Castellina in Chianti.
Aug.			70 lances	Lazio	Following the defeat, moves to guard Rome with his lances.
				Toscana	In the course of the conflict, seizes Castell’ottieri and Montacuto.
1527
June				Toscana	Begins negotiations to fight in the pay of the imperial forces against the League; suspicion of his defection convinces della Rovere to move his camp from Isola Farnese to San Giovanni near Montefiascone.
	Pitigliano	Siena		Toscana	The Sienese attack him together with Alfonso Malvezzi because he refuses to accept his status as a protected subject of the republic. He is forced to yield and to send his own ambassadors to Siena to ask for forgiveness. He submits to the republic for five years; he is also obliged to deliver every year a silver cup worth 100 scudi.
1528
Summer	Pitigliano	Siena		Toscana	Resumes the conflict with the Sienese with the support of the abbot of Farfa, Napoleone Orsini. Invades the republic from the south. In mid-July the enemy forces cross into his territory and burn all the crops. His response is to act in the same way near Sovana and Manciano.
1529
May-June				Toscana	Repeats his offensive actions near Piancastagnaio. Having received reinforcements from Napoleone Orsini, he assaults Sovana and engages in a violent fight against the opponents led by Giovanni Battista Umidi. In early June he is in turn attacked by Prete di Campiglia and the Spanish captain Piazza. His militia, commanded by Amico d’Arsoli, falls into an ambush and gets the worst of it. Mid-month, Emperor Charles V and Pope Clement VII intervene to force the two sides to negotiate peace. An accomandigia (a pact whereby the loser places himself under the protection of the winner) is signed, lasting two years and renewable up to five, under which he is required to offer, at the feast of the Assumption in mid-August (the famous Palio of Siena), a palio (a banner of precious fabric) worth 20 ducats and a silver cup weighing 20 ounces (28.30 grams per ounce). Finally, the inhabitants of the county of Pitigliano are required to buy salt at Orbetello at a fixed price.
1530
July				Toscana	Draws up his will.
1534
Jan.					Dies at the end of the month. Has the church and monastery of San Francesco built near Pitigliano. Portrait by Francesco De Rossi, known as Salviati (Palazzo della Pilotta, Parma). Marries Giulia Conti and Vittoria Frangipani della Tolfa.

SOURCES

-Con Muzio Colonna, Guido Rangoni, Rinieri della Sassetta, Ludovico Euffreducci “I quali erano huomini di grande esperienza nelle cose della guerra.” GIOVIO

-“Senza alcun dubbio per le cose, che correvano all’ora nelle guerre d’Italia, fu riputato ed honorato cavaliero.” BARTOLOMEO GIAVARINA in “Notizie storiche nella quale brevemente s’espone l’origine della nobilissima famiglia Orsina”.

-“Fu valoroso Cavaliere.” GAMURRINI