Troilo da Rossano: When Heavy Cavalry Met Swiss Pike Squares

Italian CondottieriTroilo da Rossano: When Heavy Cavalry Met Swiss Pike Squares

Brother-in-law of Francesco Sforza, he was described by contemporaries as, on the one hand, a capable commander of heavy cavalry, and on the other, a man of deplorable character. He should be seen as representative of a mode of warfare that was inevitably on the verge of transformation. In the final phase of his career, in the service of Charles the Bold (Carlo il Temerario), Duke of Burgundy, he was among the first Italian condottieri to be involved in battles that were tactically innovative. These engagements were marked by the rise of infantry forces—particularly the Swiss—in which tightly packed formations of pikemen (the square) could easily overcome traditional cavalry charges. This stood in stark contrast to earlier infantry tactics, which had relied primarily on the use of archers and crossbowmen.

Indice delle Signorie dei Condottieri: ABCDEFGIJLMNOPQRSTUVZ

Francesco Sforza’s controversial brother-in-law faced the military revolution that ended medieval warfare

Troilo da Rossano / Troilo di Muro (Troilo Orsini) of Rossano. Historians from Ascoli Piceno claim he was originally from that city and attribute to him the name Troilo Rosato dei Migliani. He held the title of count and was lord of Serra San Quirico and Maleo. He was also the brother-in-law of Francesco Sforza.

Death: 1476 ca.

Year, MonthState, Comp. venturaOpponentCommandArea of ActivityActions Undertaken and Other Salient Facts
Learns the profession of arms serving first in the companies of Paolo Orsini and then in those of Francesco Sforza.
1434
Feb.SforzaChurchRomagnaEstablishes contact with the castellan of Imola to make the city rebel against the pontificals: the maneuver is thwarted by Gattamelata and Brandolino Brandolini.
MayChurchFortebraccio MilanLazio and UmbriaWith Sarpellione leaves the siege of Montefiascone to cut the road at Vitorchiano to Niccolò Piccinino who seeks to unite his forces with those of Niccolò Fortebraccio. Camps at San Marino al Cimino with Sforza and prepares to fight: the ducal ambassador Urbano di Ortona intervenes and peace is discussed. Troilo da Rossano heads to Otricoli with Sarpellione.
JulyChurchUmbriaAt the conclusion of a truce between Francesco Sforza and Niccolò Piccinino seeks to recall Lorenzo Attendolo who has left the field because he opposes the agreement.
1435
MayUmbriaIs reported heading to Otricoli. Is captured by the braceschi.
JuneRomagnaMoves to Romagna with Sarpellione. Defeats Francesco Piccinino and Sacramoro da Parma at Maturano, captured with two hundred horses while escorting a supply convoy. Twenty are prisoners of ransom and forty oxen are seized.
1436
JuneChurchForlì MilanMarche and RomagnaAt Pesaro with Taliano Furlano. Immediately moves to Romagna to proceed to the siege of Forlì.
Nov.TuscanyAt Santa Gonda when the condotta is renewed to Francesco Sforza by the anti-Visconti league.
1438
Feb.LombardyGoes to Milan on behalf of Francesco Sforza; negotiates with Duke Filippo Maria Visconti the terms of his captain’s marriage to Bianca Maria Visconti.
1439
SpringVeniceMilanVenetoIs wounded at the siege of Lonigo by a gunshot. In April Francesco Sforza seeks to grant him lordship in the Marche of the castle of Ficino (Poggio San Vicino). The inhabitants of San Severino Marche successfully oppose this proposal.
JuneVenetoWith Niccolò da Pisa overcomes the resistance of Niccolò Piccinino and Gian Francesco Gonzaga at Soave; forces both opposing condottieri to abandon their recently constructed fortifications.
Sept.Trentino Veneto and LombardySuccessfully defends the Venetian fleet on Garda at Torbole against Niccolò Piccinino; leaves the Veronese with Guglielmo Cavalcabò, Giovanni Conti and Guerriero da Marsciano (1000 horses and 200 infantry) to rescue Brescia. Takes the mountain road north of Garda and reaches Val Sabbia and the foothills; bypasses Gavardo which Taliano Furlano had just conquered and burned on those very days.
Oct.TrentinoIs joined by Gattamelata with many horses and infantry.
Nov.Trentino LombardyMoves toward Tenno; Francesco Sforza sends him to Riva del Garda with cavalry to block the passage of Gian Francesco Gonzaga intent on joining with Niccolò Piccinino. Attacks the adversaries and repels them victoriously. Then assists Francesco Sforza and Gattamelata in the reconquest of Verona occupied three days earlier by Piccinino, Gonzaga, Luigi dal Verme with a sudden assault. Troilo da Rossano penetrates the city through the castle of San Felice and attacks the citadel. When the Visconti flee through the Porta di Santa Croce he pursues them with Sarpellione: many are the dead among the adversaries. Crosses the Mincio with 400 horses and heads toward the Brescian territory. Continues the action and subdues Val Trompia.
Dec.LombardyWith Sarpellione and Diotisalvi Lupi (1000 infantry and 200 horses) surprises the Visconti at Rodengo Saiano; captures 300 horses from them. Niccolò Piccinino withdraws and the Venetians introduce into Brescia a small convoy of munitions with 300 infantry.
1440
Jan.LombardyEscorts a new convoy of supplies to Brescia.
Mar. Apr.TuscanyIs sent with Niccolò da Pisa and Bosio Sforza to aid the Florentines, threatened by Niccolò Piccinino, at the head of 800 horses and 900 infantry.
June100 lancesUmbriaWith Paolo della Molara (280 lances) has the task of entering Città di Castello: after an initial setback, in which seven men-at-arms of Paolo della Molara are taken prisoner, overcomes all resistance capturing 70 horses from the adversaries; enters the locality. The entry of the two condottieri provokes the killing of some inhabitants: the citizenry welcomes the Florentine commissioners cheering for the Church state. At month’s end takes part in the battle of Anghiari.
Oct.Lazio Romagna and MarchePasses through Rome with Micheletto Attendolo; at month’s end with this captain, Bosio Sforza, Orso Orsini and Niccolò da Pisa crosses the Rimini area with 6000 horses to winter with troops in the march of Ancona.
1441
Jan.MarcheHas Perugian merchants detained in Fabriano with their goods as reprisal because some of his soldiers were robbed in Perugia territory. The commune of Fabriano intervenes with Troilo da Rossano and Alessandro Sforza, stationed at Fermo, to request the merchants’ release and return of their goods.
MarcheObtains as fief from Francesco Sforza Serra San Quirico.
Apr. MayRomagna and VenetoLands at Rimini with 400 horses and (May) reaches Micheletto Attendolo at Padua.
JuneLombardyParticipates in the battle of Cignano. Francesco Sforza orders him and Pietro Brunoro to attack the Visconti camp on the right where the fortifications end and where there seems to be wider access to the camp. The Venetian horses and infantry must face the adversaries until the arrival of Sforza himself with the rest of the army. Niccolò Piccinino nullifies their action by drawing Troilo da Rossano and Pietro Brunoro into a marshy area where the two condottieri are repelled. Troilo da Rossano is seriously wounded in combat: loses an eye and from then on will no longer be able to speak correctly; will also be blamed for the defeat by Sforza for not correctly interpreting his dispositions. In reality it was Sforza himself who made his troops fight in the middle of a populated center.
Aug.MarcheAt Monte San Martino.
Oct. Nov.LombardyAt the end of the conflict goes to Cremona for the marriage of Francesco Sforza with the daughter of the Duke of Milan Bianca Maria Visconti.
1442
MaySforzaChurch NaplesRomagna and MarcheLeaves Castrocaro Terme with 1000 horses and stops at Bagnolo; passes through Rimini with 800 horses; heads to Jesi where Francesco Sforza is located.
JuneIs sent to the King of Naples Alfonso d’Aragona (Alfonso of Aragon) to begin peace negotiations: takes advantage of the opportunity to contact the sovereign.
JulyMarcheIs at the Sforza camp at Monte San Martino, where some agreements are stipulated between Francesco Sforza and the king’s procurator Ignazio di Guevara.
Aug.MarcheAt San Demetrio: Alfonso d’Aragona denies any validity to the pacts signed in his name by Ignazio di Guevara; conflict resumes. Troilo da Rossano defeats the pontificals at Amandola.
Oct.MarcheAt the defense of Fabriano with Sigismondo Pandolfo Malatesta and Pietro Brunoro. Seeks to prevent passage to adversaries coming from Umbria. Attacked by surprise by Roberto da Montalboddo must retreat to Fabriano with many losses.
Nov.MarcheHas the task with Pietro Brunoro of seizing the fortress of Tolentino controlled by the pontificals: camps at Montolmo (Corridonia), sends a man into the city native to Tolentino; this man makes the adversaries understand that the inhabitants of Corridonia want to defect from the Sforza camp. 100 horses and 200 infantry leave Tolentino and are taken prisoner by the 2 Sforza captains; the city however does not desist from its purposes and remains under ecclesiastical control.
1443
Jan.LombardyFrom Sforza has the appointment as his vicar in the Cremona area.
Apr.MarcheIs reported guarding Jesi.
Aug.MarcheBetrays Francesco Sforza and deserts to the Aragonese camp with 1000 horses; delivers Jesi to the adversaries. In Cremona he is depicted with Pietro Brunoro hanged by the feet as a traitor in the Torrazzo and in the Public Palace.
Sept. Oct.Francesco Sforza takes revenge on his behavior and that of Pietro Brunoro with the construction of false evidence of treason which he has delivered to Alfonso d’Aragona: Troilo da Rossano goes to the king’s pavilion with the other captain and both are imprisoned first in the castle of Marano di Napoli and then in the capital. Their companies are plundered by the Catalans.
SpainIs imprisoned in the fortress of Satabia near Valencia; from here is transferred to the island of mud at the borders with Africa.
1450Francesco Sforza having become Duke of Milan intercedes in vain on his behalf.
1455
AutumnSpain Lombardy Lazio and CampaniaIs freed on the occasion of the marriage of a daughter of Ferrante d’Aragona with a son of Francesco Sforza. Meets with his brother-in-law who forgives him, gives him some mounts and clothes. Is sent back by the King of Naples: in transit through Viterbo meets with Corrado da Fogliano. Sforza himself presses the Aragonese to have his goods restored.
1456LombardyIn Milan.
1460
Jan.LombardyGoes to Mantua.
1462
LombardyLives in Maleo in the Lodi area. Later, in 1465, this fief will be recognized and he will be given some real estate properties nearby.
Apr.LombardyAsks the Marquis of Mantua Ludovico Gonzaga for a mount so that his son Giovanni Francesco can participate in a joust organized for Saint George’s day.
1458
Aug.LombardyAttends in Milan the signing of an agreement between Sforza and the Duke of Savoy concerning the Cocconato.
1461
Jan.LombardyIn Milan, at the funeral of Sforza’s mother Lucia Terzani.
1464/1465
Lombardy VenetoIn May 1464 he is offered to fight the Turks in Morea with Tristano Sforza. Does not find agreement on the payment offered to him and refuses to move. Instead sells the mounts of his company to Francesco Sforza’s son. In 1465 he is in Venice seeking a condotta. The authorities delay.
1466
Jan.LombardyConsiders leaving the Milanese duchy. Sells some goods and buys mounts. The rumor spreads that he has been engaged by Florentine exiles with 500 horses and 200 infantry to support the cause of Bartolomeo Colleoni (who provides him 6000 florins for this purpose) against the ducal forces. The Duke of Milan detains him by granting him the condotta previously refused (100 lances with provision of 1000 florins) and the money to return to the Bergamo condottiere.
AutumnLombardyIn the context of a global sale of revenues and jurisdictions his possessions and dominion rights over Maleo are confirmed, a fief previously belonging first to Innocenzo Cotta and then to Rabotto di Landech. At Maleo lodge also his company and those of his sons Alessandro and Giovanni Francesco. Troilo da Rossano also has a residence in Milan in a palace of the fortress of San Babila. Frequently attends court.
1467
Jan.LombardyAt month’s end abandons the duchy; takes refuge in Venetian territory. The defection has precedents: in preceding months, in fact, the new Duke of Milan Galeazzo Maria Sforza has imposed on Troilo da Rossano’s son, Alessandro, a new condotta and has done everything to prevent him from passing to the payroll of another state. Other disputes have concerned the lodging of the men of his company. Galeazzo Maria Sforza tries by all means to make the condottiere return to the duchy. The commissioner of Lodi sequesters his goods which are given to the duke’s half-brother Polidoro Sforza; at the same time the duke publicly offers conciliatory conditions for his return to the wife and son Alessandro (annual provision initially of 2000 florins, subsequently reduced to 1000; restitution of the fief of Maleo; condotta of 100 lances, equal to 300 horses; collection of horse taxes and prestanza). Troilo da Rossano delays and Galeazzo Maria Sforza does not hesitate to imprison his son Alessandro in the tower of Porta Vercellina. The measure achieves its effect; the following day the condottiere presents himself at court.
Feb.LombardyReturns to Milan; meets with the duke. The latter takes revenge by letting him know that the men of his company would be paid on Saint Sylvester’s day, perhaps of the following year.
1468
Apr.LombardyAgain abandons the Duchy of Milan. His house in Milan and the goods of Maleo are distributed to soldiers and courtiers like Pierpaolo da Fabriano and Scaramuccetto di Calabria. During the ceremony of blessing the standards on Saint George’s day his behavior (like that of Donato del Conte) is harshly criticized by the duke.
Dec.Negotiations to make him repatriate succeed.
1469
JuneVeniceCaptain g.le broken lancesLombardy and VenetoFollowing a new flight passes to the service of the Venetians. Has command of the broken lances. Places his quarters in Padua.
1471
Nov.MarcheHaving taken refuge in Pesaro territory, in the lands of Alessandro Sforza, asks to be able to return to the Duchy of Milan. Galeazzo Maria Sforza grants him no condotta.
1472
Nov.BurgundyBelgiumServes the Duke of Burgundy Charles the Bold (Carlo il Temerario). Leaves Bruges and comes to Italy to gather troops there. Contacts Bartolomeo Colleoni.
1473
Jan.Bartolomeo Colleoni accepts the proposal of the Duke of Burgundy; the Venetians intervene and the old condottiere is forced to cancel the pacts.
Feb. Apr.Veneto and TrentinoGoes to the Veronese. Then touches Trento and from here takes the road to return to Burgundy.
1474
JuneBurgundyFranceHaving obtained license from the Duke of Milan passes to the service of the Duke of Burgundy Charles the Bold. Is delivered 3500 ducats at Dijon.
JulyBurgundyEmpireGermanyIs sent to aid the Archbishop of Cologne. Participates in the siege of Neuss on the Rhine. After a year of vain attempts must withdraw.
1475
Apr.FranceIs in Franche-Comté guarding the fortress of Pontarlier. Decides to abandon it with the arrival of 8000 Swiss; 4000 Picard horses and other troops led by the Savoyard Giacomo di Vische come to his aid for which he in turn goes on the offensive. Forces the adversaries to withdraw from a castle in the area they are besieging; pursues them with 40 horses, followed by the infantry of his company and another 200 led by his son Alessandro. Reaches the Swiss while they are fording a river. Attacks a skirmish: 40 adversaries are killed against 2/3 Burgundians. The Swiss pikemen form a square. Troilo da Rossano prefers not to continue further in his action.
MayFranceArrives at Levier; reinforced by other Burgundian horses (1700 horses and many infantry) decides to assault the Swiss: they retreat in good order and stop on the banks of a river. Troilo da Rossano has part of his militias cross it to occupy a nearby hill; at night having noted the uselessness of his offensive has his men recross the watercourse and retreats.
Aug.FranceIs reported at Montbazon in Haute Saone.
Sept.FranceIs at Jussy. Complains to the Duke of Milan Galeazzo Maria Sforza because he has had his son Alessandro detained in Milan with the accusation of having given asylum in Burgundy to the exile Sforza da Cremona and the crossbowman Filippo, accused of homicide in the duchy. Moves to Serancourt; requests that twenty men-at-arms reach him from Milan to replace as many lances killed in combat or returned to Italy for various causes. Touches Gianes; 300 horses of his company raid the territory controlled by the King of France and seize a castle which is sacked and burned.
Nov.FranceAt the siege of Nancy. Charles the Bold assigns him some lands.
1476
Mar. Apr.BurgundyC. SwissSwitzerlandFaces the Swiss and the troops of the Duke of Lorraine Renato di Vaudemont (René of Vaudémont). With Antonio da Lignana has command of the second of 5 Burgundian army corps. Is defeated at Grandson where the adversaries appropriate his baggage.
June600 horsesPiedmont SwitzerlandOpposes Innocenzo Fieschi; occupies Masserano with the fortress in the Biella area. Goes to Geneva with Oliviero de la Marche and there captures the Duchess Iolanda di Savoia (Yolande of Savoy) and her children favorable to a separate peace with the Swiss. Finally takes part in the battle of Morat. The King of France Louis XI entrusts the regency of the Duchy of Savoy to Filippo di Bresse (Philip of Bresse) and the duchess remains prisoner of the Burgundians until November. Troilo da Rossano faces the Swiss; with Antonio da Lignana is reproached by Charles the Bold because his lances do not want to expose themselves to the enemy artillery fire; stung in his pride advances at the head of 3000 men. The Swiss block the charge of his troops with arquebus fire; his infantry flees. In the clash his son Giovanni Francesco and Antonio da Lignana are killed; heavy are the losses recorded by his heavy cavalry.
JulySwitzerlandHis company disintegrates. Of 1000 infantry only 80 remain. All survivors return to Italy.
Aug.FranceIs reported at la Rivière where the Duke of Burgundy entrusts him with command of 300 lances and 2000 infantry.
Probably dies at the end of the year. Marries Bona Caterina da Fogliano, uterine sister of Francesco Sforza and Corrado da Fogliano. His secretary is Gaspare Broglio.

Sources

-“Magnifici viri dilecti et fidelis, capitanei nostri et conductoris gentium nostrarum armatarum Ytalie.” Da una lettera di Carlo il Temerario, duca di Borgogna, al duca di Milano Galeazzo Maria Sforza, riportata dal SESTAN

-“Troilo era ingiusto, oltraggioso non meno agli amici che a’ nimici.” CAVALCANTI

-“…quel gentile/ che fu benigno di singular merto/di Troilo dico.” SPIRITO

-“Erat is quidem praeferoci (quo quidem re multos infensos fecerat) ingenio.” FACIO

-Con Sigismondo Pandolfo Malatesta e Pietro Brunoro “Capitano de’ soldati valorosi.” COLUCCI

-Con Niccolò da Pisa, Micheletto Attendolo, Bosio Sforza e Orso Orsini “Tucti capitanii e homini degnii.” BROGLIO

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