Gaspare da San Severino: The Mercenary Captain Between Glory and Ruin

Italian CondottieriGaspare da San Severino: The Mercenary Captain Between Glory and Ruin

Son of Roberto da San Severino. He was nicknamed Fracassa for his strength and was described by contemporaries as the "new Achilles" and the son of Mars. A skilled, impetuous, and astute condottiero, he embodied the classic figure of the great mercenary captain. His primary ambition was to carry out brilliant military operations and to gather honors and wealth. In this sense, he represented the quintessential Renaissance man-at-arms, with both the virtues and flaws typical of his era. As the years passed, his reputation gradually faded, partly due to his ambiguous behavior in various circumstances. His end was inevitably marked by frustration and misery.

Indice delle Signorie dei Condottieri: ABCDEFGIJLMNOPQRSTUVZ

A Condottiero’s Struggle for Power and Fortune

Gaspare da San Severino (Il Fracassa, Fracasso, Gaspare da San Severino d’Aragona). He was nicknamed Fracasso for his impetuous nature and physical strength. Lord of Piadena, Spineda, Calvatone, Cittadella, Mandello del Lario, Bellano, and Varenna. He was the son of Roberto da San Severino; brother of Galeazzo da San Severino, Giovan Francesco da San Severino, and Antonio Maria da San Severino; half-brother of Ottaviano da San Severino, Giulio da San Severino, and Faccendino; and uncle of Roberto da San Severino.

Born: 1455
Death: 1519, May

Year, MonthState, Comp. venturaOpponentCommandArea of ActivityActions Undertaken and Other Salient Facts
Year, MonthState, Comp. venturaOpponentCommandArea of ActivityActions Undertaken and Other Salient Facts
1475
Feb.Firenze50 lancesToscanaObtains from the Florentines, together with his brothers Galeazzo and Giovan Francesco, a joint condotta of 50 men-at-arms valued at 5500 ducats.
Apr.ToscanaReported in Pisa.
1477
MayToscana and LiguriaStill located in Pisa. In the same month, the ducal forces secure the surrender of a Genoese exile who controls the strongholds of Montaggio and Savignone. He is given as a hostage to this man as a sign of adherence to the signed agreements.
1478
MayFirenzeNapoli, ChiesaToscanaIn Castiglion Fiorentino.
JulyToscanaIn Cortona.
Aug.ToscanaIn Poggio Imperiale (Poggibonsi).
Dec.ToscanaContracts the plague. The King of Naples Ferrante d’Aragona sends doctors and medicines to his camp to treat him.
1480
JulyEmiliaDistinguishes himself in Ferrara during a joust held in the square.
Nov.PioPioEmiliaAssists the uncles of his wife Margherita Pio in recovering the lordship of Carpi. Leaves Colorno; overcomes obstacles at Brescello and approaches Carpi hoping to take it by negotiation. Borso da Correggio enters Carpi in defense of Marco Pio with 100 Este men-at-arms. Upon arriving under the walls, he sees the Carpi resident who led the plot hanged; he tries to persuade the soldiers defending the city to revolt but is pushed back by cannon and crossbow fire. He withdraws, pursued by men-at-arms, mounted crossbowmen, infantry, and local peasants, with whom he has a brief skirmish. At the end of the month, he takes shelter in Guastalla.
1481
MilanoLombardiaCalled to be part of the ducal council.
Nov.VenetoIn Ariano Polesine with his brother Antonio Maria da San Severino hunting roe deer and wild boars. At the end of the month, he takes part in a grand joust in Ferrara, also attended by his brothers Galeazzo and Antonio Maria da San Severino; the judges Francesco da Ortona and Leonello Brandolini grant him the palm of victory.
1482
Jan.–Feb.San SeverinoMilanoPiemonte, LombardiaLeaves Milan unexpectedly with his brothers Galeazzo and Antonio Maria. He joins his father against the ducal forces. He is besieged in Pontecurone by the Sforza army led by Costanzo Sforza and Gian Giacomo da Trivulzio. Captured, he is taken to Milan in early February, from where he manages to escape.
Mar.–Apr.Piemonte, Liguria, FranceFinds refuge first in Garbagna, land of Obietto Fieschi, without resistance. From there, he continues to Quarto dei Mille, where he embarks for France; with his father Roberto’s help, he leaves that country and moves into Ligurian territories under Obietto Fieschi.
MayVeneziaFerrara, Milano, NapoliToscanaBrought by the Serenissima to Siena for the War of Ferrara.
JuneRomagnaLeaves Romagna with his brother Giovan Francesco, embarks at Chioggia, and arrives in Venice. He is received by the Doge; he then moves on to Padua and from there proceeds to the camp.
JulyVeneto, EmiliaBreaks into the Polesine with his brother Antonio Maria da San Severino and the proveditor Piero Marcello; captures the bastion of Canda (defended by Corradino da Savana with 25 soldiers), Castelguglielmo (perhaps surrendered for money by Angelo Saltarelli and Giovanni da Cavo), the tower of San Donato, the fortress of Arquà Polesine, and two bastions of Pontecchio Polesine. He crosses the Po and lodges in Pontelagoscuro, in the residence of Ambrogio Contrari, with 8 cavalry squadrons under the artillery fire of the Este bastion. Attacked by Federico da Montefeltro, he recrosses the river; a few days later, he clashes with the men-at-arms of Lanfranco Rangoni.
Aug.–Sept.VenetoIntercepts 300 infantrymen under the command of Giovanni Cataneo and Niccolò dall’Arpa trying to enter Rovigo; occupies Lendinara (surrendered by negotiation) and Rovigo, where he lodges in the suburb of Santa Sofia. He secures the castle by negotiation, defended by 150 infantry under Niccolò Ariosto, Giacomo Sacrati, and Lanfranco Rangoni. Struck by a malaria attack, he is forced to leave the field temporarily.
Oct.VenetoRecovered, leaves Padua and returns to the Pontelagoscuro camp with his father Roberto.
Nov.EmiliaManages to cross the Po with 14 cavalry squadrons and 2000 infantry, repels an assault by Gian Giacomo da Trivulzio who must abandon a floating bridge toward Francolino. Plants the flags of San Marco in the Barco of Ercole d’Este, seizes Copparo, and raids the area, capturing livestock worth an estimated 2000 ducats.
1483
Jan.EmiliaCrosses the Po di Volano, arrives at Contrapò by night, makes prisoners, and again raids livestock, which is led back to the Polesine.
Mar.EmiliaAlong with Galeotto della Mirandola and Rodolfo Gonzaga, moves from Francolino and Pontelagoscuro toward the Barco (20 cavalry squadrons and 4000 infantry), enters Ferrara’s suburbs, and is forced to withdraw.
JuneEmiliaFollows his father to the Brescia area when, replaced by Renato di Lorena in commanding troops, the latter is transferred there.
Aug.LombardiaIn the Brescia area. The inhabitants of Barbariga oppose his entry into the town; in retaliation, he sets fire to surrounding haylofts. Soon after, he has a small skirmish with the enemy at Santa Giustina.
Sept.LombardiaRaids Asola, burns the straw collected for the enemy’s lodgings, and seizes much livestock. The Marquis of Mantua complains, and the Serenissima compensates him for the damages.
Oct.Veneto, EmiliaJoins his father in a 60-mile night maneuver; anticipates the Gonzaga forces at Melara, blocking their advance; heads toward the Ferrarese territory.
Nov.Veneto, LombardiaDefeated at Melara by Cristoforo da Montecchio, he leaves the Veneto with the proveditor Marco Antonio Morosini for Sant’Eufemia della Fonte in the Brescia area. Tries to retake Quinzano d’Oglio with eight cavalry squadrons. Around the same time, he attacks Bagnolo Mella with Deifobo dell’Anguillara, forcing the surrender of Giulio and Virginio Orsini, who are immediately released.
Dec.LombardiaCrosses the Oglio with the proveditor general Niccolò Pesaro. Occupies Rocca Tristana near Soncino, seizing 1500 staia of grain, 50 carts of hay, and 100 oxen. Twenty men-at-arms are killed, and another 40 captured in the clash.
1484
Feb.LombardiaIn Brescia for the funeral of Leonardo da Martinengo.
JuneLombardiaLeaves Verolanuova with his father Roberto and the proveditor general Luca Pisani; at the head of 9000 men (20 cavalry squadrons, 3000 infantry, 500 stradioti, and local militias), engages in a skirmish with little success between Romano di Lombardia and Martinengo, occupies Boltiere at the expense of Bartolomeo Turco, as well as Vailate; moves into the Milanese area, linking up with Guelph sympathizers of that territory. Conquers and sacks the fortress of Calcio, where Fermo Secco and 40 men-at-arms are captured (he imposes a ransom of 2000 ducats). A few days later, takes Pumenengo by agreement, withdrawing only when Niccolò Orsini advances against him with twenty squadrons.
JulyLombardiaParticipates in peace negotiations with ambassadors of the Duke of Milan Giovanni Galeazzo Maria Sforza.
Sept.VenetoAt the signing of the peace treaty, he visits Venice with his father. The Doge Giovanni Mocenigo meets them on the Bucentaur near San Clemente.
1485
Feb.Veneto, Romagna, LombardiaTakes part in a major joust in Piazza San Marco, Venice: wins first prize with his brother Antonio Maria (each receiving twenty braccia of gold cloth worth twelve ducats a braccio and a pouch containing 25 ducats); second prize goes to his other brother Galeazzo. He appears at the celebration in the Doge’s Palace held by the Compagnia della Calza in honor of his father’s wife; prompted by his father, he tries in vain to intercede for three soldiers guilty of causing serious unrest in Rialto. Later, traveling incognito between Imola and Forlì, he arouses the suspicions of the Florentines and of Girolamo Riario. He meets some Bolognese exiles, a Sienese exile, and has multiple encounters with Gian Francesco da Tolentino. Passes through Ravenna, where he organizes a joust, and then returns to Lombardia.
Apr.Veneto, EmiliaVisits Verona with his father and his brother Antonio Maria; warmly received in the city and hosted at the bishop’s residence. Goes to Ferrara to take part in another chivalric tournament.
VenetoBack again in Verona. Wins first prize at a joust in which his brother Antonio Maria comes second.
Oct.–Dec.ChiesaNapoliMarche, LazioServes under Pope Innocent VIII (Innocenzo VIII). After gathering troops in the Marche, he is at Campo dei Fiori in Rome with his father and brother Antonio Maria for their review. He meets the Pope. In mid-Dec., moves to defend Viterbo with sixteen cavalry companies and some infantry against Virginio Orsini. In the following days, passes through Vetralla, Montefiascone, Bagnoregio, Bolsena, Marta, and other locations to secure grain for Viterbo and his troops.
1486
Jan.Lazio, Veneto, EmiliaIs seriously wounded by an arquebus shot to the mouth (the bullet goes through his cheek) in an assault on Ponte Nomentano to expel the Orsini. The surviving defenders (twenty soldiers) surrender unconditionally: six artillerymen have their hands cut off; upon seeing this, five arquebusiers throw themselves into the Tiber and drown or are killed; the remaining soldiers are wounded and robbed of their weapons. Carried to Padua for treatment, he loses many teeth and is left with a deformed mouth. Once recovered, he goes to Ferrara for the wedding of Giulio Tassoni.
Mar.LazioReturns to Rome; spends time jousting and competing in races, such as one from Campo dei Fiori to St. Peter’s, which he wins.
1487
Jan.EmiliaTakes part in a joust in Bologna for the wedding of Annibale Bentivoglio and Lucrezia d’Este, daughter of Duke Ercole of Ferrara.
Aug.VeneziaAustria300 cavalryTrentino, VenetoAt the camp of Serravalle all’Adige; tasked with capturing Arco alongside the proveditor general Girolamo Marcello. By late month, returns to Verona.
Nov.TrentinoWith the peace signed with Duke Sigismondo of Austria, he leaves the Valsugana for winter quarters.
Dec.500 cavalryVenetoThe Venetians renew his condotta. He resides in Cittadella.
1490
Feb.LombardiaJoins Marquis Francesco Gonzaga of Mantua at Belgioioso near Mantua. Takes part in some jousts.
MayRomagnaIn Forlì.
JulyThe Venetians pay him 1000 ducats for old arrears.
Aug.Milano100 cavalry
1491
Jan.LombardiaEmerges victorious at a Milan joust arranged by Ludovico Sforza for his wedding with Beatrice d’Este, another daughter of Duke Ercole of Ferrara.
JulyRomagnaSent to Cotignola with 300 cavalry to punish some local rebels. In response, the Florentines send Paolo Orsini with 400 cavalry to the area.
1492
Apr.Emilia, LazioStays in Bologna, hosted in his palace by Giovanni Bentivoglio. In Rome, he lodges at the Church of Sant’Anastasia with his brother, Cardinal Federico, participating in the conclave that elects Rodrigo Borgia as Pope.
JuneThe Duke of Calabria Alfonso d’Aragona sends him a banner depicting a flying stag.
1493
Feb.EmiliaIn Ferrara with Ludovico Sforza. Again takes part in a joust.
Apr.Chiesa40 light cavalryLazioHired by Pope Alexander VI (Alessandro VI) with 40 mounted crossbowmen in case of conflict with Virginio Orsini, who, against the Pope’s wishes, purchased Anguillara Sabazia, Cerveteri, and other small castles from Franceschetto Cybo.
MayRomagna, Lazio, EmiliaLeaves Romagna for Rome with several cavalry squadrons; when the threat of war subsides, returns to Ferrara as a guest of Ercole d’Este. He again participates in a joust.
JuneRomagnaIn Cesena.
July–Aug.ChiesaGualdo CattaneoLazio, UmbriaBack in Rome; camps with his troops outside the city at Prima Porta, where a hailstorm causes more than 1500 ducats of damage. Nonetheless, on the following Sunday, he reviews his troops in St. Peter’s Square before Alexander VI. Shortly afterward, he joins Guidobaldo da Montefeltro in the plain of Bettona to besiege Gualdo Cattaneo.
Sept.MarcheIn Jesi. The Duke of Ferrara seizes 3000 ducats in Ferrara that had been deposited for him on the bank of Paolo Tassini (once Ercole d’Este’s minister, who fell from grace) to cover a promised dowry to a sister of Tassini himself.
Nov.UmbriaIn Orvieto, accompanying the Pope.
1494
Apr.LazioPasses through Bologna on his way to Rome.
MayChiesadella RovereLazioWith Fabrizio Colonna and Niccolò Orsini, seizes the fortress of Ostia, defended by Giovanni della Rovere, Prefect of Rome, on behalf of his brother, Cardinal Giuliano (the future Pope Julius II).
JuneMarcheSummoned to Jesi by the Luogotenente of the Marche Giulio Cesare da Varano to finalize a truce between Fermo and Ascoli Piceno. Since Fermo refuses to comply, Giulio Cesare da Varano suggests he attack the city; instead, he has Fermo’s fields harvested and heads for Fermo.
JulyMilanoLombardiaIn Cotignola and in Milan. Awarded three castles, including Piadena and Cavatore, worth 2000 ducats a year.
Sept.MilanoNapoli300 cavalryLiguria, Emilia, RomagnaIn the Genoa area to counter the threat by Federico d’Aragona and exiles. Along with his brothers Galeazzo and Antonio Maria and Giovanni Adorno, he attacks Obietto Fieschi in Rapallo, who has landed with 3000 infantry. He engages them on the bridge to the monastery of Vallecristi while Luigi d’Orleans (the future Luigi XII) attacks from the sea. Repelled initially, the outcome is decided by Adorno’s supporters and the French fleet artillery (18 galleys, 6 galleons, and 9 large ships). One to two hundred enemies are killed, and Giulio Orsini, Fregosino, and Orlando Fregoso are taken prisoner. Afterward, he heads to the Emilia region, reaches Borgo San Donnino (Fidenza), supplies the troops of Montpensier, goes to Modena, tries to rob Annibale Bentivoglio on patrol near Bologna, and joins the ducal forces in Sant’Agata with 50 light cavalry, 30 mounted crossbowmen, 12 lances, and 200 poorly equipped infantry. At the camp, Morgante Baglioni challenges him to single combat in vain. Moves with his brother Giovan Francesco to the Zaniolo/Genivolo moat in the Ferrarese territory with seven cavalry squadrons, 600 French lances, and 4000 Swiss. He feels certain the enemy will withdraw soon and refuses to have his men dig trenches.
Oct.350 cavalryRomagnaFails in an attempt to ambush Niccolò Orsini in the Cesena area. Rides out with his brother Giovan Francesco to San Paolino near Bagnacavallo; blocks the way for Giovanni Gonzaga, forcing him back to Mantua with 600 cavalry. Participates in the assault on the castle of Mordano, which results in 300 defenders killed, either in the fight or by drowning as they attempt to flee. He saves some women from having their noses cut off by the French. In the same days, King Carlo VIII of France grants him a condotta of 50 light cavalry.
Nov.Romagna, Emilia, LombardiaHelps Guido Guerra da Bagno with 500 light cavalry near Cesena, capturing Bagnara di Romagna. Leaves the region with Giovan Francesco da San Severino, passes through Bologna, where Annibale Bentivoglio escorts him out of the gate. Meets Niccolò da Correggio in Cremona.
1495
Jan.MilanoFirenzeRomagna, ToscanaLudovico Sforza sends him to Caterina Sforza in Forlì to persuade her to leave the city and go to Milan. She refuses. He is then dispatched to help Pisa against Florence. He is in dire financial straits and forced to pawn his silver.
Feb.LombardiaReturns to Cremona.
Apr.Emilia, LombardiaFirst in Ferrara with 25 cavalry but receives no greetings. Lodges in the ducal court. Goes to Mantua; meets Paolo Albanese, who offers himself to the ducal forces. Stops in the Piacenza and Parma regions to raise 100 light cavalry (57 mounted crossbowmen and 43 stradioti).
MayLombardiaIn Milan for the official investiture of Ludovico Sforza as Duke. Negotiates for a 200-lance condotta from the League.
JuneMilanoFrancia100 lancesLombardia, ToscanaIn Vigevano, where he receives the Venetian proveditor Bernardo Contarini with 635 stradioti. When his brother Giovan Francesco is suspected of treason, he and Galeazzo ask for possession of Giovan Francesco’s Milan palace; the accusation proves unfounded, and Ludovico Sforza grants him the properties and rights once held by Chiara Sforza, Pieve d’Incino, and Valassina with Mandello del Lario, Bellano, Varenna, Dervio, Introzzo. The inhabitants refuse to swear allegiance to him. Goes to defend Pontremoli, where the French slip past his guard toward Parma.
JulyEmilia, PiemonteParticipates in the Battle of Fornovo; afterward sent to Tortona with 100 light cavalry and 200 German infantry to defend the territory from the retreating French. Together with his brother Giovan Francesco, he helps the enemy cross the Scrivia and provides them with supplies, hastening their departure from Lombardia. Meets King Carlo VIII of France. Moves to besiege Novara.
Aug.PiemonteAt Novara, positioned at the gate leading to Trecate and the borough of San Gaudenzio. Attends the ceremony in which Francesco Gonzaga receives the staff and banner of Captain General of the League. Fights the Fieschi bands. Obtains permission from his brother Galeazzo to carry out a raid with over 100 lances in the Vercelli area, returning with 22 captives of ransom value, 200 oxen, and 900 sheep. Rumors about his double dealing grow, fueled by his haughty behavior toward Francesco Gonzaga.
Sept.PisaFirenze400 cavalryToscanaSent to help the Pisans with cavalry and Genoese infantry. Arrives in Pisa in mid-month. Dispatches a herald to the Florentine camp, demanding cessation of hostilities within four days and threatening war otherwise. His troops intercept a small convoy at la Vettola carrying hemp and pitch needed to caulk boats on the Arno.
Oct.ToscanaRides on Vicopisano; some of his men enter Lake Bientina by boat to catch spies, who are killed or captured. Although peace is officially concluded between the King of France and the Duke of Milan, he remains in Pisa to enjoy properties he owns there. In reality, on Ludovico Sforza’s orders, he obstructs the Florentines—intent on recovering Lunigiana lands gained by the Genoese during the French invasion—with 100 cavalry and 400 infantry.
Dec.ToscanaA dispute arises between his men and those of Giannotto Francese, causing casualties on both sides. The Pisans, out of fear, side with the French. Angry, he leaves the city with part of the garrison and returns to Lombardia.
1496
Feb.LombardiaIn his fief of Spineda.
Mar.EmiliaIn the Ferrarese territory.
JulyLombardiaWelcomes the Emperor Maximilian of Austria in Bellano; during the ceremony, he and other Lombard lords hold a canopy above him. Then greets him in Como on behalf of Ludovico Sforza.
Oct.MilanoFranciaPiemonte, LiguriaIn Tortona, commanding the Sforza troops after his brother Galeazzo falls ill. Blocks the advance of Trivulzio at Altare.
Dec.PiemonteDefends the Duchy’s borders near Alessandria.
1497
Jan.Receives money from Ludovico Sforza to outfit his men-at-arms and face the French (35–40 ducats each).
Mar.FirenzeVenezia, PisaToscana, EmiliaLearning of his condotta with the Florentines, Ludovico Sforza, through Galeazzo Visconti, orders him not to leave or at least not to use his own company. With Rondanello da Lugo, he defends the fortress of Marradi, repels 400 stradioti, and recovers the town. Clashes with Paolo Vitelli and leaves the camp with 150 light cavalry, taking four days to reach Bologna from Florence.
Apr.LombardiaBreaks with the Duke of Milan; retires to Spineda, where he negotiates with the Venetians. He is banned from the Milanese territory, and his assets are confiscated. Reconciles shortly thereafter with the Duke.
JulyPioPioEmiliaGoes to Carpi under the pretext of visiting his ailing brother Antonio Maria; supports Giberto Pio against Lionello Pio. Forced to leave the city by Ercole d’Este’s pressure, he departs with spoils worth 10000 ducats, refusing to return them.
Aug.LombardiaIn Mantua, accorded all honors.
Sept.LombardiaIn Brescia for the jousts organized by Podestà Giorgio Corner in honor of his sister Caterina, former Queen of Cyprus. Lodges for eight days in the palace of Giovan Francesco Gambara with a retinue of 150. Takes part in a joust with his brother Galeazzo. After the festivities, he is called to Pizzighettone by the Duke for a company muster.
Oct.LombardiaInspects with his brother Galeazzo the posts on the Swiss border and in the Novara area. Then in Milan.
Dec.LombardiaLeaves Milan on a mission from Ludovico Sforza to Francesco Gonzaga in Mantua and to the Emperor returning to Germany after a failed expedition to Pisa.
1498
Jan.–Feb.Lombardia, Trentino, AustriaDeparts Milan carrying three sets of jousting arms. Invited to Innsbruck for a tournament hosted by Maximilian of Austria during Carnival. Passes through Trento with an entourage of 40 cavalry. During the tournament, he is toppled by a man-at-arms, which severely damages his helmet.
Mar.LombardiaReturns to Milan laden with gifts; he himself gave the Emperor four grey horses and a suit of armor worth a total of 400 ducats.
MayMilano500 cavalryLombardiaOrdered to head to Tuscany to confront the Venetian troops.
JuneLombardiaWith Corrado Stanga and Giovanni da Gallarate, goes to Mantua to ratify the condotta of Francesco Gonzaga with the Duke of Milan. There, his men clash with some of the Marquis’s cavalry over old enmities: 25 are wounded in the fight.
JulyMilanoVenezia500 cavalryLombardia, Romagna, EmiliaMusters his men in Soncino; goes to Cotignola and Forlì. With 200 lances, he protects Caterina Sforza from Venetian threats. Then proceeds to Ferrara, where he reviews 200 men-at-arms of Alfonso d’Este in Milanese service.
Aug.RomagnaA guest in Cesena of Polidoro Tiberti.
Sept.Lombardia, Romagna, ToscanaNearing the end of his contract, he requests a condotta from the Venetians, who refuse. Returns to Milan with 15 cavalry for the funeral of Lorenzino de’ Medici, a favorite of Ludovico Sforza. Goes back to Romagna. Persuades Astorre Manfredi of Faenza not to grant passage in the Lamone Valley to Venetian forces (2000 infantry and 300 light cavalry) heading for the Casentino. Meets Giovanni da Casale in Cotignola, then belatedly heads with 50 light cavalry and 60 lances to Marradi to oppose the Venetians advancing in support of Pisa and the Medici. Finally, moves toward Forlì with 50 men-at-arms from Alfonso d’Este’s company.
Oct.Romagna, ToscanaReaches Castrocaro Terme; at the request of the Florentine commissioner Antonio Giacomini, proceeds to Modigliana with 300 cavalry and 500 infantry. There, he also meets Caterina Sforza, who grants him 500 of the 1000 florins he demands. At Modigliana, joined by his brother Giovan Francesco with 1000 infantry and 300 men-at-arms, plus another 100 Este men-at-arms. Frees Marradi from Guidobaldo da Montefeltro’s siege; with Dionigi Naldi and Ottaviano Manfredi, attacks Brisighella but is driven back. Urges his brother to attack again, but the latter refuses; angered (with Antonio Giacomini intervening to calm them), he returns to Modigliana, passes through the Bologna area, and heads to Tuscany with 60 light cavalry. With Ranuccio da Marciano, arrives in Arezzo, concerned about a plot favoring the Medici. His mission is to defend the Casentino, not to undertake more aggressive actions.
Nov.Romagna, ToscanaEnters Forlì; fortifies himself in the city to repel possible attacks, while threatening Venetian possessions in the Ravenna area. Observes a duel in Forlì between Alberto Marcheselli and Alberto Aldovrandini. The enemy withdraw from Villafranca; he returns to Cotignola, harasses Faenza, and raids the territory up to Russi. Penetrates the Ravenna area with Dionigi Naldi, burning twenty-eight houses in a village. Moves on San Benedetto in Alpe and Dicomano with 400 cavalry; from there heads to Pontassieve and on through the Valdarno to Arezzo. The Florentines grow suspicious and dispatch Commissioner Antonio Giacomini to monitor him. He goes to the Casentino with 500 lances and 500 infantry, mostly from his brother Giovan Francesco’s contingent (the brother is ill), to prevent the area from rising in favor of the Medici.
Dec.ToscanaArrives in Borgo San Niccolò; in Poppi he meets Paolo Vitelli; they decide to attack Fronzola and Monte della Verna. Near Pieve Santo Stefano, he seizes 400 infantry and 200 cavalry en route from the Urbino area to reinforce Bibbiena. He too marches on Bibbiena to besiege them, but a lack of funds stalls any offensive. His men are forced to sell their mounts, replacing them with horses captured from Bartolomeo d’Alviano at Marzano.
1499
Jan.Toscana, RomagnaWith Paolo Vitelli in Pieve Santo Stefano, commanding 350 light cavalry and 1200 infantry. Some of his men desert due to unpaid wages; Ludovico Sforza closes the passes leading to Lombardia but sends him 1000 ducats. Attacks Montalone, defended by Carlo Orsini. Near Verghereto, he captures Marco di Santi, secretary of the proveditor Piero Marcello, who, with 400 infantry and 200 cavalry, is headed for Bibbiena carrying money and supplies. He refuses to deliver him to the Florentines (as Vitelli wants) and sends him instead to Città di Castello, pocketing the 2000 ducats found on him and sharing them only with Francesco da Montedoglio. His term expires.
Feb.ToscanaStill in Pieve Santo Stefano, musters 1000 enlisted men. Imposes a 4000-ducat ransom on Marco di Santi, then declines it in hopes of keeping good relations with the Venetians. His disputes with Paolo Vitelli intensify, as he criticizes Vitelli’s caution. Receives 6000 ducats from the Duke of Milan to recruit more infantry. Besieges Bibbiena. By late month, leaves the Casentino upon the formation of a league between the French and Venetians against the Sforzas.
Mar.Toscana, Lombardia, EmiliaSuspected of treason for contacts with the enemy, he is declared a rebel by the Sforza commissioner Galeazzo Visconti and has two hours to leave Milan, two days to exit the Duchy. Seeks refuge in Bologna with Annibale and Alessandro Bentivoglio.
Apr.PisaFirenzeToscana, Lombardia, EmiliaJoins the defense of Pisa on behalf of the Genoese, then leaves and withdraws to Spineda. Requests a Venetian condotta; heads to Ferrara while the Venetian Council of Ten debates his situation.
MayFriuli, EmiliaPresses the Emperor for the investiture of Pordenone; returns to Ferrara; is wounded in the thigh by a lance fragment during a joust.
JuneLombardia, RomagnaThrough the mediation of his brothers, reconciles with Ludovico Sforza, to whom he cedes the castle of Piadena as a guarantee. Tasked with organizing jousts in Milan. Goes to Forlì to borrow 2000 ducats from a Jewish lender.
JulyLombardiaThe castle of Piadena is returned to him. Reenters Ludovico Sforza’s service.
Aug.MilanoFranciaPiemonteRejects an offer from Lucca—leadership of its troops at 40000 florins annually—and faces the French in the Alessandria area with little success.
Sept.LombardiaFollowing Ludovico Sforza’s flight to Austria before the French, he first retreats to Cremona among his relatives the Ponzoni, then to Milan, seeking a condotta from King Luigi XII. Participates in the King’s solemn entry into the city, but his attempts at favor lead nowhere. Exiled to Ferrara.
Oct.–Nov.Veneto, EmiliaThe Venetians strip the San Severino brothers of Cittadella: Gaspare is suspected of wanting to hand it to the Imperial forces. Desires to return to the Veneto but is stopped at Verona, so he goes back to Ferrara. Offers his services to the Lady of Forlì against Cesare Borgia, demanding 3000 ducats, which she deems too high.
1500
Feb.SforzaFrancia, VeneziaLombardiaJoins Ludovico Sforza in his attempt to retake the Duchy of Milan. In Pavia and Vigevano, he advises the Duke to attack the French at Mortara.
Mar.Piemonte, LombardiaAt the siege of Novara; his wife in Ferrara is destitute, forced to pawn linen for a sack of wheat. Moves to Ghiaradadda to counter Venetian troops.
Apr.Lombardia, PiemonteAmbushes a column of 300 infantry heading to Lodi, killing most of them. With Ludovico Sforza, takes Novara. The French attack while he is playing chess with the Duke. In the ensuing rout, he is captured, along with his brothers Galeazzo and Antonio Maria, due to the Swiss betrayal. Taken as he tries to flee in disguise, he is jailed in the Castello Sforzesco. Freed upon paying a ransom of 200 ducats.
June–JulyLombardia, Emilia, TrentinoIn Mantua with Marco da Martinengo and brother Galeazzo; forced to leave by pressure from the French. Escapes to Ferrara by boat, then to Bondeno, where he meets the Venetian vicedomino and complains about losing Cittadella. Sends his meager belongings (only four chests) to Germany; they are confiscated en route. Crosses Torbole with 30 cavalry alongside his brother.
Aug.TrentinoAt Trento; the Venetians return his seized chests, taken by mistake. So impoverished that the city’s captain donates two horses to him.
LazioTaunted by Cesare Borgia at a Vatican gathering before Pope Alexander VI; he wrestles with Taddeo della Volpe, and the Duke of Valentinois intervenes to separate them.
1502
Feb.ToscanaAt month’s end, goes to Pisa for the Emperor.
Apr.PisaFirenzeLombardia, ToscanaFree of condotte, he stays penniless in Sacchetta near Mantua, then tries to serve Pisa against Florence. Attacked by local forces from Barga, he shelters in a nearby church on the border with the Este domain. The tower he occupies is set on fire; he is captured along with Niccolò Piccinino (son of Giovanni Giacomo), Bernardino da Cremona, and Giorgio della Barba, then taken to Barga and Florence. This sparks a diplomatic incident between Florence and Este.
JuneToscanaMaximilian of Austria intervenes for him. His brother, Cardinal Federico da San Severino, secures his release.
Sept.EmiliaIn Bologna, well received as usual by Annibale and Ermes Bentivoglio, lodging in their palace. In Ferrara, Ercole d’Este grants him a pension of 500 libbre.
Oct.ChiesaRomagnaIn Cesare Borgia’s service. Joins the Duke of Valentinois at Imola with Lucio Malvezzi.
Nov.ChiesaRebel Condottieri150 light cavalryRomagnaIn Imola with 150 mounted crossbowmen. Held in esteem by Cesare Borgia. Opposes the condottieri rebelling against the Papal State.
Dec.RomagnaIn Cesena; Borgia nominally enfeoffs him with Civitella di Romagna, Valdoppio, and two other castles near Meldola. By late month, he is left without a condotta.
1503
Jan.–Mar.ChiesaOrsiniRomagna, LazioImprisoned by Borgia, then freed by March. Goes to Rome with his brother Antonio Maria. Receives a Papal condotta; besieges the Orsini in Ceri.
Apr.FranciaSpagnaAbruzziRaids the Abruzzi region to push inhabitants to side with the French over the Spanish. Enters L’Aquila with 104 cavalry and 30 infantry, lodging at the house of Andrea Conti.
MayAbruzziRaises many infantry after setbacks for the French faction.
JuneAbruzziLeaves L’Aquila for Barisciano to confront the enemy; meeting none, he returns. In mid-month, with Girolamo Gaglioffi, orders the city’s church bells rung as an alarm. Advances toward Rocca di Cambio but is repelled by Colonna forces. Back in L’Aquila, where Saccoccio da Spoleto arrives with 160 infantry and 15 cavalry, many carrying plague and spreading it in the city.
JulyAbruzzi, Umbria, LazioThe arrival of Fabrizio Colonna with numerous troops forces him to abandon L’Aquila with Gaglioffi. Withdraws to Cittaducale with 300 cavalry; many of his men are robbed or killed. Passes via Orvieto, is sighted near Bolsena, and stops in San Lorenzo for several days at the locals’ expense.
Sept.LazioMeets Cesare Borgia. Escorts Cardinal Giuliano della Rovere as far as Ronciglione.
Oct.50 lancesLazio, CampaniaIn Rome, ready to join the French in the Kingdom of Naples against the Spanish. The war ends in Spanish victory, leaving him once again without a condotta.
1504
Jan.LazioIn Rome, favored by Pope Julius II (Giulio II), rumored to be appointed lieutenant of Francesco Maria della Rovere’s company.
Mar.MarcheIn the Montefeltro area.
Apr.80 lancesGranted command of 80 lances out of the 300 in Guidobaldo da Montefeltro’s company, with an annual stipend of 3000 ducats.
MayRomagna, MarcheIn Forlì, trying to persuade the men of Borgia to cede the fortress to the Papal forces. Goes to Urbino, then back to Romagna. Unsatisfied with his finances.
JuneRomagnaIn Cesena with 50 cavalry. Denied lodging costs by the inhabitants, he must stay at an inn.
Aug.Marche, RomagnaIn Pesaro. Returns to Forlì, secures the fortress on behalf of the Pope from Castellan Consalvo di Mirafonte.
Oct.Toscana, RomagnaSpotted in the Casentino, in Forlì, and Imola.
1506
Sept.–Nov.ChiesaBolognaEmiliaSupports the Papal forces against the Bentivoglio, rulers of Bologna. In Nov., enters the city for Pope Julius II’s solemn entrance.
1507
Jan.EmiliaFalls from favor; goes to Bologna.
Mar.ChiesaAscoli PicenoCaptain GeneralMarcheCommands the Papal army against Ascoli Piceno. The city surrenders the following month.
Mar.–Apr.ChiesaAscoli PicenoCaptain GeneralMarcheLeading the Papal forces against Ascoli Piceno, which capitulates by agreement. In April, the Pope sends him to aid Genoa in its war with the French.
1508
Mar.His brother, Cardinal Federico da San Severino, presses the Venetians to grant him a condotta.
1509
Feb.LazioLiving in Rome. Again offers his services to the Venetians for a 150-man-at-arms condotta, receiving another refusal.
Apr.–JuneVenezia, Impero, Francia, FirenzeFrancia, VeneziaMarche, Lombardia, VenetoRepeats his proposal to the Serenissima from Ancona. The Council of Savi now accepts, awarding him a condotta of 100 men-at-arms and 200 light cavalry. Goes to Osimo; Pope Julius II obstructs his departure. In May, he arrives in Cremona disguised as a shepherd. After the defeat at Agnadello, he is given command of some men-at-arms who escaped capture. Gaspare da San Severino then defects to the victors, travels via Modena with 30 cavalry, presents himself to the King of France. Lured by the Imperial promise of recovering Cittadella and Montorio Veronese, he enters Emperor Maximilian d’Austria’s service.
July200 cavalryVenetoIn Vicenza. Commands 200 cavalry hired by the Florentines.
Aug.VenetoAttempts to take possession of Cittadella; faces opposition from Pandolfo Malatesta, who also claims the town. Malatesta, too, has defected from the Venetians to the Imperial side. Gaspare da San Severino joins the siege of Padua with 300 cavalry; he secretly contacts the Venetians, sending emissaries to Venice, but gains no hearing. Because of his attitude, he soon loses his condotta and is assigned only to oversee the artillery.
Sept.–Oct.60 cavalryVenetoStill at Padua’s siege. Allegedly bribed by the Venetians, he persuades the Spanish to retreat after a failed assault on the Bastion of Codalunga. Once Imperial forces withdraw, he is left with 500 cavalry around Castelfranco Veneto and Camposampiero, then placed in charge of Vicenza with 5000 infantry. His official condotta is now 50 lances and 200 light cavalry, but he only commands 60 cavalry in practice. In mid-Sept., his son Gabriele drowns in the Brenta.
Nov.VenetoAgain exhibits ambiguous behavior; sends his chancellor Alvise Marzucchi to Venice. Meanwhile, with Prince Rodolfo of Anhalt, defends Vicenza. Makes a sortie but is driven back through the Porta di Monte Berico. Discouraged, after four days he tasks Simone da Porto with negotiating the surrender; he is among the first to leave the city with twenty men-at-arms, followed by the infantry. At the end of the month, he is in Verona. Receives from the Emperor command of the Italian troops, replacing Costantino Arianiti, forced to return to Rome after quarreling with La Palisse, who challenged him to a duel.
Dec.Alto Adige, VenetoMeets Maximilian d’Austria in Bolzano. Returns to defend Verona.
1510
Feb.25 cavalryVenetoWith Alberto da Serego, attempts a raid near Villafranca di Verona; falls into an ambush by enemy stradioti, losing 15 mounted crossbowmen killed and 30 captured. A few days later, Rodolfo of Anhalt imprisons him in the Castle of San Pietro, suspecting he intends to defect to the Venetians.
MayGermaniaJailed in Germany, he manages to send an envoy to Venice. His brother Federico presses for his release.
Oct.Freed, offers again his services to the Venetians in vain.
Dec.Emilia, LombardiaMid-month in Parma. Later in Milan with his brother, Cardinal Federico. Charles II d’Amboise (Chaumont) welcomes him politely.
1511
JulySienaFirenzeCaptain GeneralLombardia, ToscanaAgain tries to join the Venetians. The Council of Ten debates his possible appointment as Captain General. Moves to Mantua and is hired by Siena.
Oct.Toscana, Alto AdigePeace is made between Siena and Florence, leaving Gaspare da San Severino jobless. Goes to Bolzano, proposing to the Venetians that he serve as plenipotentiary in negotiating peace with the Imperial and French sides.
1512
Jan.–Apr.Lombardia, VenetoLeaves Mantua for Venice, lodging at San Bartolomeo di Ponziana. Meets Doge Andrea Loredan, renews his offers. In Feb., appears before the Collegio; again, the Council of Ten debates awarding him a condotta. Allowed to follow the army without formal appointment; granted a yearly pension of 2000 ducats. In Padua and Montagnana. Summoned to the Collegio to advise on a possible attack on Legnago. In Mar., the Collegio remains undecided. Meanwhile, he attends many public ceremonies with the Doge, such as greeting Cardinal Sedunense, and holiday events. Now staying on the Giudecca in the former palace of Pandolfo Malatesta, he receives more money (over 350 ducats in four months).
May–Aug.VenetoRepeatedly appears in official events with the Doge, repeatedly presses for an active command; his requests continue over the following months.
Sept.–Dec.VenetoSeeks Venetian permission to leave; spotted with the Doge in Oct. The Collegio, overburdened, refuses him an official hearing; in Dec., responds to yet another money request with merely 25 ducats.
1513
Feb.VenetoRenewed pleas for a suitable role and better funding. His brother Federico is suspected by the Venetians of mediating between the French and Duke Massimiliano Sforza, making Gaspare’s position increasingly inconvenient. He is allowed to depart.
Mar.Marche, LazioReceives 150 ducats after some disputes to travel to Urbino. Joins Francesco Maria della Rovere, accompanies him to Rome for the coronation of the new Pope Leo X, where he holds the Papal banner for the Duke.
1515
JulyEmiliaReceives money from the Papal treasury and travels to Bologna under Giuliano de’ Medici, Captain General of the Papal forces, serving as counselor.
Dec.The Council of Savi evaluates his possible command for the Venetians; the proposal is rejected because he is disliked by Governor General Teodoro da Trivulzio and is seen as too aligned with the Papal party.
1516
Feb.EmiliaIn Bologna, again fruitlessly approaches the Venetians.
SummerLombardiaWith the deaths of Giuliano de’ Medici and his brother Cardinal Federico da San Severino, he loses his last supporters in the Papal Curia. From Spineda, he sends more envoys to Venice seeking a condotta, then secures a position as counselor to the new Papal Captain General Lorenzo de’ Medici.
1519
MayLazioRetired in Rome, spends his final years along the Tiber in worsening poverty and frustration. Dies at the end of the month. A portrait of him (dated 1491) is found in an incunable of the Divine Comedy edited by the Franciscan Pietro da Figino and illuminated by Antonio Grifo. Mentioned by Luigi Pulci in his letters. Marries Margherita Orsini and Margherita Pio.

Sources

-“Quasi un altro Marte e fulgore in battaglia era da li nemici temuto per il terrore del nome..Qual’è valentissimo soldato.” SANUDO

-“Era comunemente appellato il figlio della fortuna, il parto del valore.” MUONI

-“Guerriero rustico e millantatore.” PASOLINI

-“Il Fracasso rappresenta la figura classica del grande capitano di ventura. Invano si cerca nella sua lunga carriera un sentimento di amor patrio; la sua principale ambizione è quella di compiere brillanti operazioni militari e di raccogliere onori e ricchezze. Venezia, benché avesse una grandissima stima della sua abilità di capitano.. non volle saperne di lui perché non ne aveva fiducia. Nel ritratto di questo personaggio si rispecchia il classico uomo d’arme del rinascimento nei suoi difetti e nelle sue virtù.” ADAMI

-“L’Achille di quell’età, il miglior Capitano de’ tempi andati.” DE’ CRESCENZI

-“Huomo nelle armi esperto.” GHIRARDACCI

-“Che per la sua fortezza si vendicò il nome di Fracasso, fracassando tante lanze nelle giostre.” ALBERTI

-“Vedrai Frachasso far paterne prove/ Armato in sella e cum victorie excelse/ Alto ingegno, alto cor, dolceze pronpte/ E tra i più nobil spirti lo divelse.” Da un sonetto di G.B. REFRIGERIO in occasione della morte del padre Roberto

-“Persona experta et sagace nell’arte de gente d’arme.” T. DI SILVESTRO

-“El quale era animoso e ghaiardo e feroze.” CORPUS CHRONIC. BONOMIENSIUM

-“Costui fu di molto gran cuore e di animo assai guerriero.” CANTALICIO

-“Qui estoit un tres-gracieux et bon gendarme.” Da un estratto del giornale di A. De La Vigne riportato dal GODEFROY

-“Che si era trovato alle principali fazioni, capitano di grande nome.” ALVISI

-“Impetuoso soldato.” BACCHELLI

-“Du eccellente nelle guerre.” SANSOVINO

-“Capitano accreditato.” VERDIZZOTTI

-“Capitano di grande fama.” DONATI

-“Ne l’arme gli è Fracasso ardito e francho/ Pien dico di forteza e di cervello.” CORDO

-“Fracasso biastemava tutto il mondo/ ben che havesse la lingua mal disposta,/ nel biastemar non se icapava un pelo/ cossì con furia a nimici s’accosti/ urtando e pacatando or questo or quillo/ a che li denti a chi el cervello amosta (rompe)/ assai ne va occidendo e pacotendo/ e pur ognora sempre biastemando.” E.C. RINUCCI

-Battaglia di Novara “Parea quel giorno Fracasso un marcello/ che fulminasse con la spada in mano.” Da ” La guerra del Turco e la presa di Modone” in GUERRE IN OTTAVA RIMA

-“Fracasso che giamai in guerra stanco/ Combatte con l’azza el brando in mano.” Da “Guerre orrende d’Italia” in GUERRE IN OTTAVA RIMA

-“Viene Attilio in guerra sia,/ che ruina el mondo abasso,/ questo è il forte gran Frasasso/ che combatte disperato.” Dal lamento del reame di Napoli di G.B. DRAGONCINO riportato da MEDIN-FRATI

-“Un vero esperto della professione militare.” ARCANGELI

-All’assedio di Padova “Col retroguardo seguiva fraccasso/ Hom d’alto ingenio, e di natura forte/ disposto far gir molti a capo basso/ è il primo di padoa ne le porte./…/ (Alla difesa di Vicenza)” Costui con più di cento valorosi/ homeni d’arme, & fanteria fiorita/ per far ristar quei piani sanguinosi/ a far a più d’un par lassar la vita/ contra marcheschi trati, & furiosi/ con intrepido cor, e fronte ardita/ col stocco in man mise in la battaglia/ troncando ogni armatura, e fina maglia./ Ben si potea costui nomar Fraccasso/ sì fraccassava la marchesca gente/ gettando hor questo hor quello a capo basso/ chi morto, e chi ferito stranamente.” DEGLI AGOSTINI

-Meglio conosciuto come Fracasso o Fracassa è stato un condottiero e diplomatico italiano. Famoso per il furore bellico e l’eccezionale audacia, fu anche definito dai contemporanei “il nuovo Achille” per la sua apparente indistruttibilità, nonché figlio di Marte e Fulgore in battaglia… Proprio come il padre Roberto, Fracasso fu violento, impulsivo, permaloso, facile all’ira: numerosi sono gli episodi ricordati nelle varie fonti delle volte in cui insultò personalità anche importanti o in seguito ad una lite se ne andò adiratissimo. Aveva il vizio della bestemmia. Nondimeno fu assennato e di buon cuore, sebbene Luigi XII lo definisca “un pazzo”.” WIKIPEDIA

Specific biographies

V. ADAMI Il carteggio di un capitano di ventura. Gaspare S. Severino detto Fracasso (1475-1518)

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