Azzo da Castello: The Raiding Master of Medieval Italy

Italian CondottieriAzzo da Castello: The Raiding Master of Medieval Italy

He was regarded by his contemporaries as a master of war—brave and experienced. Over the course of his career, he had the opportunity to measure himself—either as ally or adversary depending on circumstance—against the greatest condottieri of his age, such as John Hawkwood (Giovanni Acuto) and Alberic of Barbiano (Alberico da Barbiano). His true specialty was not pitched battles but rather raids and plundering carried out in the territories of his enemies. After many conflicts, clashes, and struggles across central Italy, he met his end in Ferrara during a mock combat—a tournament staged to demonstrate, in real conditions, to the young Marquis Niccolò d'Este, what a real engagement was like.

Indice delle Signorie dei Condottieri: ABCDEFGIJLMNOPQRSTUVZ

The man who raided enemy lands and died for spectacle

AZZO DA CASTELLO (Azzo da Castel Lombardo). From Spezzano. Lord of Spezzano, Formigine, and Sigillo.

Death: 1395, February

Year, MonthState, Mercenary CompanyOpponentCommandArea of ActivityActions Undertaken and Other Salient Facts
1370
EmiliaBecomes lord of Spezzano.
MilanFerraraEmiliaRebels against the Este family (Estensi) in favor of the Visconti family (Visconti).
1377
Oct.FlorenceChurchMarchesFights for the Florentines in the War of the Eight Saints (guerra degli Otto Santi). With Lutz Von Landau (Lucio Lando), Giovanni degli Ubaldini and John Hawkwood (Giovanni Acuto), he fights on behalf of the lords of Fermo (Rinaldo da Monteverde) and of Matelica against the papal condottiero Rodolfo da Varano.
1381
MayMercenary CompanySienaTuscanyThe Sienese grant him 5,000 florins so that he does not cross their territory with his company.
Nov.Mercenary CompanyFermoMarchesBreaks into the territory of Fermo with John Hawkwood (Giovanni Acuto) and Lucio Lando; encamps in the counties of Chiaravalle and Montottone, follows Boffo da Massa to Rotella and Montalto; is repelled from Montottone.
1384NaplesHouse of AnjouCampaniaServes under Alberico da Barbiano against the troops of Louis I of Anjou (Luigi d’Angiò).
1385
Feb.NaplesChurchRomagna and MarchesLeaves Romagna with Alberico da Barbiano and the gonfalonier of Bologna Ramberto Bacilieri; crosses the territories of the Malatesta family and reaches Fano, where the inhabitants supply him with provisions for four days.
Apr.Mercenary CompanyFermoMarchesImposes on the commune of Fermo a levy of 4,000 ducats.
MayMercenary CompanyMarchesJoins with Ceccolo Broglia, Brandolino Brandolini, Giovanni da Barbiano, Conte da Carrara and Boldrino da Panicale; devastates the Marches, capturing men and raiding livestock. Occupies various lands of the Papal States.
JuneMarchesPasses before the Porta di San Marco at Fermo and heads towards Ripatransone.
1388
JunePaduaMilanLombardyClashes with Ceccolo Broglia and Brandolino Brandolini in the Mantua area. Quickly reaches an agreement with his opponents.
1389
ChurchAntipopeApuliaOpposes in Apulia the troops of Antipope Clement VII. Is granted by the pontifical authorities a salary of 600 ducats.
Nov.With the death of Urban VI and the accession of Boniface IX, he is dismissed with the accusation of not having fulfilled his duty.
1390
Jan.UrbinoRiminiRomagna and MarchesIs hired by the Count of Urbino, Antonio da Montefeltro, to fight the Malatesta family, who have seized Corinaldo. Carries out raids in the territories of Rimini, Cesena, Fossombrone and Senigallia.
1391
Feb.Mercenary CompanyJesi, Camerino, AnconaMarchesHaving been discharged by Antonio da Montefeltro, with Bindo da Montopoli he conducts a raid in the counties of Jesi and Camerino; threatens Ancona and forces the commune to hire him on behalf of the league against the papal forces. He is granted 8,000 ducats.
Aug.UrbinoRimini150 lancesMarches and RomagnaFights for the Montefeltro against the Malatesta. Routinely defeats his opponents, leading raids as far as Cesena.
Sept.–Oct.ChurchMarchesAfter the failure of a compromise proposed by the rector of the March, Andrea Tomacelli, to the Parliament of Macerata (late September), his condotta is confirmed by Ancona on behalf of their allies. New militias under Niccolò da Montefeltro, Bartolomeo Gonzaga and Noschino da Veroli are raised. Hostilities pit, on one side, Tomacelli’s forces (including the companies of Giovanni da Barbiano, Count of Carrara, the Malatesta, and the communes of Ascoli Piceno, Recanati, Macerata, Montecchio (Treia), and Osimo), against, on the other side, the militias of Ancona, Fermo and those of Gentile da Varano.
Dec.EmiliaThe Este withdraw all condemnations against him (he had been condemned in absentia to decapitation years earlier); Niccolò d’Este officially invests him with the fief of Spezzano.
1392
June–JulyMercenary Company of PerugiaPerugia, Città di Castello, Florence, Siena, Pisa, Lucca, Mercenary CompanyMarches, Umbria and TuscanyAn agreement is reached between Gentile da Varano and their allies with the opposing group led by Andrea Tomacelli. He then leaves the Marches. With him, alongside Broglia and Brandolini, join Giovanni da Barbiano and Giovanni Tedesco da Pietramala, forming the Company of Saint George (Compagnia di San Giorgio) with 4,000 cavalry. Driven by exiles of Perugia, Assisi, Gualdo Tadino and Nocera Umbra, he attacks Perugia, ravages its territory, plunders livestock and takes some prisoners. He is paid 4,000 florins to withdraw; obtains by treaty the castle of Sigillo (of which he makes himself lord), moves towards Colle della Colommella, reaches Ponte Felcino and enters the territory of Gubbio. He threatens Città di Castello and Florence, demanding 100,000 florins. The republic mobilizes defenses but ultimately agrees to pay 40,000 florins in exchange for a year’s truce. Other levies are imposed on the Sienese (5,000 florins, the total raid cost 11,112 florins due to gifts to captains), the Pisans (12,000 florins) and the Lucchesi (8,000 florins). Azzo da Castello returns to Perugia, serves for Perugia and with John Beltoft counters his former allies.
Aug.Urbino Mercenary CompanyRiminiUmbria, Romagna and MarchesThe Perugians request a truce from Biordo dei Michelotti and other condottieri; Azzo da Castello rejoins the Company of Saint George. He joins Antonio da Montefeltro to plunder territories of the Malatesta. Leading 760 cavalry and many infantry, he raids Cesena, Rimini, Fossombrone and Senigallia. At month’s end he is summoned by Gentile da Varano and Ancona; his militias, linked with those of Biordo dei Michelotti, are provisioned at the expense of neighbouring communes.
Sept.Camerino, Ancona, Fermo, Mercenary CompanyChurch, PerugiaMarches and UmbriaWith Biordo dei Michelotti, he rides through the Papal States. He faces opponents between Osimo, Castelfidardo and Macerata while the Malatesta, allied with the papal rector, raid towards Fiumesino, seizing a herd of pigs taken to Precozzano near Ripe di Senigallia. He links with the Company of Saint George and Corrado Lando, but the forces soon dissolve due to internal discord. Azzo da Castello then continues alone, threatening Nocera Umbra.
Oct.–Nov.Ancona, Recanati, FermoChurchMarches and UmbriaHe is again contracted by the communes of Ancona and Fermo and by Gentile da Varano; opposes Brandolino Brandolini, Giovanni da Barbiano, Ceccolo Broglia and Count of Carrara (2,500 cavalry), hired by Andrea Tomacelli. Ancona and Gentile da Varano ally with the communes against the papal forces. In November he crosses the territory of Città di Castello.
1393
Mar.MarchesUpon conclusion of a general peace agreement concerning the Marches, he and the captains (including Noschino da Veroli) undertake to abstain from violence in the region for one year.
Apr.Mercenary CompanyBologna, Florence, FerraraHe unites with Corrado Lando, Giovanni da Barbiano, Count of Carrara and Biordo dei Michelotti. A company of 2,500 cavalry and many infantry is formed. Neighbouring states grant condotte to the captains: the Este grant Azzo da Castello a salary; Florence grants payments to Corrado Lando; Bologna to Giovanni da Barbiano and Count of Carrara.
MayUmbriaHe is invited by the Florentines not to harass the territory of Città di Castello.
June–JulyMercenary CompanyArceviaMarchesWith Biordo dei Michelotti, he forces Rocca Contrada (Arcevia) to pay a levy. The following month Boniface IX must assure the commune he will not entrust its government to Biordo dei Michelotti or other condottieri.
Aug.Mercenary CompanyPerugiaUmbriaHe seizes Sigillo while Giovanni Tedesco da Pietramala occupies Castiglione del Lago. The prompt arrival of Biordo dei Michelotti, mediated by Ugolino Casali, persuades Azzo da Castello to cede the locality for 5,000 florins. He is then received with honors in Perugia.
Sept.Mercenary CompanyChurchMarches400 men from the former company of Boldrino da Panicale join his troops; he allies with Biordo dei Michelotti (2,500 cavalry and many infantry) and marches on Macerata where Boldrino da Panicale was murdered two years earlier. He devastates the territory, cuts vineyards and trees, defeats papal forces at Penna San Giovanni and captures Andrea Tomacelli, brother of Boniface IX. He sacks Macerata; the Florentines intervene and force the inhabitants to hand over the body of Panicale and pay a levy of 1,000 florins. The Pope promises another 10,000 florins within one month. They leave the Marches on promise not to ravage the Papal States for one year.
Oct.TuscanyLeaves Tuscany to move to Lombardy.
1394
Jan.FerraraHouse of EsteEmiliaHired by the regency council of the Este state, he faces the troops of Azzo d’Este; is granted an annual provision of 2,000 ducats. In the same month he agrees with Città di Castello to enter its service in November. He is promised a monthly provision of 1,600 florins.
Feb.EmiliaBesieges Castellarano. Due to winter severity and the arrival of Visconti reinforcements, he is forced to withdraw.
Mar.Ancona, FermoExiles of OsimoRomagna, Marches and UmbriaHe is reproached by the Florentines for causing damage in the lands of Pino Ordelaffi and the Marquis d’Este. He returns to the Marches and, with Biordo dei Michelotti, fights for Ancona against Osimo. He is then called by Antonio Aceti of Fermo to counter local exiles barricaded in Montegranaro. Encamping by Girifalco fortress, they demand 10,000 ducats (later reduced to 5,000). The Perugians grant him citizenship and a house. He travels to Perugia with Corrado Prospero, and the magistrates allocate 400 florins for his reception with the German captain.
Apr.Mercenary CompanyFlorenceTuscanyThe Florentines pay him in exchange for a year’s immunity for their territory and allies. He sacks Borgo San Sepolcro because its inhabitants refuse to oppose Bartolomeo da Pietramala.
JulyMercenary CompanySiena, Pisa, Città di CastelloUmbria and TuscanyHe leaves the Perugian territory with Biordo dei Michelotti and Corrado di Altinberg, crosses Sansepolcro and enters Tuscany to plunder Siena and Pisa. Received by the communes with 20,000 florins (through ambassadors of Gian Galeazzo Visconti), he devastates Città di Castello. Pressured by the Florentines, he sacks Selci, Celalba and Porcina, forcing them to pay 500 florins.
Aug.Mercenary Company, FerraraForlì, House of EsteRomagna and EmiliaHe advances on Forlì and states refusing a levy. At campaign’s end, he, Biordo dei Michelotti and Corrado di Altinberg pass through Forlì and part ways: Azzo da Castello remains in Ferrara on the Este payroll; Michelotti returns to Perugia; Altinberg to Ravenna. Azzo da Castello again faces Azzo d’Este and encamps between Sassuolo and Formigine, besieging the latter.
Sept.EmiliaQuells the rebellion led by Francesco da Sassuolo, Ato di Rodiglia, Filippo da Pisa and Giordano da Savignano. The Marquis d’Este invests him with Formigine.
1395
Jan.Mercenary Company (Compagnia di ventura)Fermo, Osimo, AnconaMarchesHe is in the territory of Fermo with Biordo dei Michelotti. He imposes levies on Osimo and Ancona; obtains 1,000 florins from Fermo.
Feb.FerraraHouse of Este (Este)Captain GeneralEmiliaTravels to Ferrara to discuss a war plan against Azzo d’Este. The young Niccolò d’Este arranges a tournament at Belfiore. During the demonstration, Antonio degli Obizzi’s mount stumbles and injures Azzo’s left knee. He is taken to a nearby palace, where he dies the following night. He is buried in the cathedral of Ferrara; his solemn funeral is attended by Marquis Niccolò d’Este and many inhabitants, his pennant featuring Saint George displayed.

Sources

-“Valoroso Maestro di guerra.” MURATORI

-“Capitano molto riputato.” PIGNA

-“Huomo valoroso e prode.” SARDI

-“Uomo nell’arte della guerra a quel tempo rinomatissimo.. Valoroso Condottier d’armi.” TIRABOSCHI

-“Capitano di sperimentato valore.” VEDRIANI

-“Dux famosus armigerorum.” DELAITO

-“Dopo la morte del Paneri (Boldrino da Panicale), che avvenne per tradimento del Tomacelli (Andrea), fratello di papa Bonifacio IX, Azzo fu tra i più ostinati assedianti di Macerata, e quando la città si arrese gareggiò con gli altri suoi compagni in efferatezza e in brutalità. Le ossa di Boldrino furono da lui tenute per lungo tempo come insegna della sua Compagnia e come eccitamento di furente vendetta.” ARGEGNI

Featured image: Wikimedia

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