Siege of Castelnuovo The Siege of Castelnuovo was an engagement during the Ottoman - Habsburg struggle for control of the Mediterranean , which took place in July 1539 in the walled town of Castelnuovo , present day Herceg Novi , Montenegro . Castelnuovo had been conquered by elements of various Spanish tercios the year before during the failed campaign of the Holy League against the Ottoman Empire in Eastern Mediterranean waters . The walled town was besieged by land and sea by a powerful Ottoman army under Admiral Hayreddin Barbarossa , who offered an honorable surrender to the defenders . These terms were rejected by the Spanish commanding officer Francisco de Sarmiento and his captains even though they knew that the Holy League ' s fleet , defeated at the Battle of Preveza , could not relieve them . During the siege the Barbarossa ' s army suffered heavy losses due to the stubborn resistance of Sarmiento ' s men . However , Castelnuovo eventually fell into Ottoman hands and almost all the Spanish defenders , including Sarmiento , were killed . The loss of the town ended the Christian attempt to gain control of the Eastern Mediterranean . The courage displayed by the Old Tercio of Naples , however , was praised and admired throughout Europe and was the subject of numerous poems and songs . Background . In 1538 the main danger to the Christianity in Europe was the expansion of the Ottoman Empire . The armies of the Sultan Suleiman the Magnificent had been stopped at Vienna in 1529 . In the Mediterranean , a Christian offensive attempted to eliminate the danger of the great Turkish fleet in 1535 , when a strong armada under Don Álvaro de Bazán and Andrea Doria captured the port of Tunis , expelling Admiral Hayreddin Barbarossa from the waters of the Western Mediterranean . The Ottoman Admiral was then required to return to Constantinople , where he was appointed commander of a great fleet to conduct a campaign against the Republic of Venice ' s possessions in the Ionian Sea . Barbarossa captured the islands of Syros , Aegina , Ios , Paros , Tinos , Karpathos , Kasos , Naxos , and Corfu . The Italian cities of Otranto and Ugento and the fortress of Castro , in the province of Lecce , were also looted . The Republic of Venice , frightened by the loss of their possessions and the ruin of their trade , conducted a vigorous campaign for the creation of a " Holy League " to recover the lost territories and expel the Ottomans from the sea . In February 1538 , Pope Paul III succeeded in creating a league which united the Papacy itself , the Republic of Venice , the Empire of Charles V , the Archduchy of Austria and the Knights of Malta . The Allied fleet for the campaign was supposed to consist of 200 galley s and another 100 auxiliary ships , and the army of about 50 , 000 infantry and 4 , 500 cavalry . But only 130 galleys and an army of around 15 , 000 infantry , mostly Spaniards , were all that could be gathered . The command of the fleet was given nominally to the Genoese Andrea Doria , but Vicenzo Capello and Marco Grimaldi , commanding officers of the Papal and Venetian fleets respectively , had almost twice as many ships as Doria . The commander of the army was unquestionably Hernando Gonzaga , Viceroy of Sicily . Differences among the commanders of the fleet diminished its effectiveness against an experienced opponent like Barbarossa . This was seen in the Battle of Preveza , fought in the Gulf of Arta . But the Holy League fleet provided support to the land forces that landed on the Dalmatian coast and captured the town of Castelnuovo . This small town was a strategic fortress between the Venetian possessions of Cattaro and Ragusa in the area known as Venetian Albania . Venice therefore claimed ownership of the city , but Charles V refused to cede it . This was the beginning of the end of the Holy League . The town of Castelnuovo was garrisoned with approximately 4 , 000 men . The main force was a Tercio of Spanish veteran soldiers numbering about 3 , 500 men under the experienced Maestro de Campo Francisco Sarmiento de Mendoza y Manuel . This Tercio , named Tercio of Castelnuovo , was formed by 15 flags ( companies ) belonging to other tercios , amongst them the Old Tercio of Lombardy , dissolved the year before after a mutiny for lack of pay . The 15 captains in charge of this flags were Machín de Munguía , Álvaro de Mendoza , Pedro de Sotomayor , Juan Vizcaíno , Luis Cerón , Jaime de Masquefá , Luis de Haro , Sancho de Frías , Olivera , Silva , Cambrana , Alcocer , Cusán , Borgoñón and Lázaro de Coron . Among the garrison there were also 150 light cavalry soldiers , a small contingent of Greek soldiers and Knights under Ándres Escrápula , and some artillery pieces managed by 15 gunners under captain Juan de Urrés . The chaplain of Andrea Doria , named Jeremías , also remained in Castelnuovo along with 40 clerics and traders and was appointed bishop of the town . The reason for the garrison ' s large numbers was that Castelnuovo was projected to be the beachhead for a great offensive against the heart of the Ottoman Empire . But the fate of the troops who were in the fortress depended entirely on the support of the fleet , and this had been defeated by Barbarossa at Preveza before the capture of Castelnuovo . Moreover , in a short time Venice withdrew from the Holy League after accepting a disadvantageous agreement with the Ottomans . Without Venetian ships , the Allied fleet had no chance to defeat the Ottoman fleet commanded by Barbarossa , who was by this time supported by another experienced officer , Turgut Reis . Siege . First maneuvers . Sultan Suleiman the Magnificent ordered Barbarossa to reorganize and rearm his fleet during the winter months to have it ready for the battle in the spring of 1539 . 10 , 000 infantry soldiers and 4 , 000 Janissaries were embarked aboard the warships to reinforce the troops of the galleys . According to the orders received , Barbarossa ' s army , numbering about 200 ships with 20 , 000 fighting men aboard , would blockade Castelnuevo by sea while the forces of the Ottoman governor of Bosnia , a Persian named Ulamen , would besiege the fortress by land in command of 30 , 000 soldiers . Sarmiento , meanwhile , used the peaceful months prior to the siege to improve the defenses of the town repairing walls and bastions and building new fortifications . But he could not do much due to a lack of means , as there was no plan to fortify the town since it was supposed to function as a beachhead . Captain Alcocer was sent to Spain with instructions to call for help ; Pedro de Sotomayor was sent to Sicily and Captain Zambrana to Brindisi , all in vain . Andrea Doria , who was in Otranto with 47 Imperial and 4 Maltese galleys , received news of Castelnuovo ' s situation , but given the inferiority of his fleet he sent a message to Sarmiento recommending him to surrender . In June Barbarossa sent 30 galleys to block the entrance of the Gulf of Cattaro . The vessels reached Castelnuovo on 12 June and disembarked a thousand soldiers with the aim of finding water and capturing Spanish soldiers or local civilians to gain information . Once the Spanish were warned of their enemy ' s presence , Sarmiento dispatched three companies under Captain Machín de Munguía and the cavalry under Lázaro de Corón to attack them before lunchtime . After a fierce fight the Ottoman landing party was forced to re - embark , although it returned in the afternoon . Then it was beaten by Francisco de Sarmiento in person , who was waiting for a new attempt together with Captains Álvaro de Mendoza , Olivera and Juan Vizcaíno , and 600 soldiers . Three hundred Ottomans were killed during the battle , and another 30 captured . The remainder escaped to their ships . On 18 July Barbarossa arrived with the main force and immediately began to land troops and artillery while waiting for the arrival of Ulamen , who came along with his army a few days later . The Ottoman pioneer s spent five days digging trench es and building ramparts for 44 heavy siege guns carried aboard Barbarossa ' s fleet or by Ulamen ' s troops , and even smoothed the fields around Castelnuovo to facilitate maneuvers . Castelnuovo was also bombarded by sea , as ten pieces had been previously embarked aboard the galleys . The Spanish , meanwhile , undertook several sorties to obstruct the siege works . These raids inflicted many casualties , among them Agi , one of Barbarossa ' s favorite captains . Another sortie by a Spanish force of 800 men surprised several units of Janissaries who were attempting to storm the walls of Castlenuovo , killing most of them and leaving the field strewn with corpses . When Barbarossa was informed about the setback , he severely reprimanded his officers , as the losses of the Ottoman elite corps were difficult to replace . He gave orders forbidding skirmishes to avoid a repeat of the defeat . Great assault . By 23 July , Barbarossa ' s army was ready to begin a general assault and his artillery prepared to break down the walls of Castelnuovo . Enjoying a vast numerical superiority over the Spanish garrison , which was completely isolated and unable to receive support or supplies , Barbarossa offered an honorable surrender to the Spanish . Sarmiento and his men would be granted a safe passage to Italy , the soldiers retaining their weapons and flags . Barbarossa added to his offer the incentive of giving each soldier 20 ducats . His only demand to Sarmiento was the abandonment of his artillery and gunpowder . Two squad corporals of Captain Vizcaino ' s company , Juan Alcaraz and Francisco de Tapia , managed to return to Naples and write their view of events many years later . They recorded the answer given to Barbarossa that " " the Maestro de Campo consulted with all the captains , and the captains with his officers , and they decided that they preferred to die in service of God and His Majesty . " " The great assault on the city was launched shortly after , and lasted all day . It was costly in lives , as the Ottomans employed both infantry and artillery at the same time to assault and bombard Castelnuovo , resulting in heavy casualties among the Ottomans themselves due to both friendly fire and Spanish defending . During the night the Spanish improved their defenses and plugged the gaps opened in the walls . When the attack was resumed the next morning , Saint James Day , Bishop Jeremías remained with the soldiers , encouraging them and confessing those who were mortally wounded along the attacked perimeter . About 6 , 000 Ottoman soldiers were killed in the bloody assault , while the Spanish suffered only 50 killed ; although the number of men who died from their wounds was probably large . Encouraged by the successful defense , several Spanish soldiers decided to conduct a surprise raid on the Ottoman camp with the approval of Sarmiento . Thus , one morning , 600 men took the unprepared besiegers by surprise . In some places the assault could not be stopped , and panic spread among the Ottomans . Many troops broke and ran , including some Janissaries who fled throughout their own camp breaking down the tent s , including that of Barbarossa . The Admiral ' s personal guard feared for the safety of its lord , and , ignoring his protests , took him to the galleys along with the standard of the Sultan . During the following days most of the artillery concentrated its fire on a fort in the upper town . Barbarossa thought that it was the key point of Castelnuovo ' s fortifications and proposed to capture it . The remaining cannons , meantime , continued firing at the fragile walls of the town . On 4 August , Barbarossa ordered an assault against the ruins of the fort , which was now completely shattered , with its casemates ruined . As a major point of the defense , Sarmiento had reinforced the garrison and removed the wounded in the preceding days . The assault began at dawn and the battle lasted all day . Captain Machín of Munguía distinguished himself in the fight , leading the defenders with great courage . By nightfall the remnants of the Spanish garrison retreated to the walls of the town with their wounded , leaving the ruined castle in Barbarossa ' s hands . The day was very costly in lives . Of the Spanish officers defending the castle only Captains Masquefá , Munguía , Haro and a corporal surnamed Galaz survived . The remainder had been killed in the battle . Among the very few survivors that the Ottomans captured , they found three deserters . These were immediately brought to Barbarossa and encouraged the Admiral to continue with the assaults , reporting that the Spanish had suffered heavy casualties , lacked gunpowder and shot , and were mostly injured and exhausted . Ottoman capture . On 5 August a new attack was launched against the walls . Barbarossa , after the report of the Spanish deserters , was sure that he could soon capture Castelnuevo . All the Janissaries took part in the action , and the cavalry was ordered to dismount to join the general assault . Despite the overwhelming numerical superiority of the Ottoman troops , the Spanish defense was successful , as no more than a tower of the wall fell to the besiegers that day . Sarmiento ordered his sappers to prepare a mine to destroy the tower , but the attempt failed when an unexpected burst of the gunpowder killed the soldiers who were working in the mine . At dawn on the following day a heavy downpour ruined the matchlock s of the harquebus es , the few remaining pieces of artillery , and the last gunpowder . The fight was therefore sustained only with sword s , pike s and knives , and the wounded Spanish soldiers were forced to take up arms and help defend the walls . Only the dying men remained in the hospital . Surprisingly , the few surviving Spanish managed to repel the assault . The last and definitive attack took place the next morning . Francisco de Sarmiento , on horseback , was wounded in the face by three arrows , but he continued to encourage his men . Demolished by heavy gunfire , the ruins of the walls became indefensible . Sarmiento then ordered the 600 Spanish survivors to retreat . His idea consisted of defending a castle in the lower city where the civilian population of Castelnuovo had taken refuge . Although the withdrawal was made in perfect order and discipline , Sarmiento and his men found that the doors of the castle were walled at their arrival . Sarmiento was offered a rope to raise him to the walls , but refused and responded " " Never God wants that I was saved and my companions were lost without me " " . After that he joined Machín de Munguía , Juan Vizcaíno and Sancho Frias to lead the last stand . Surrounded by the Ottoman army , the last Spanish soldiers fought back to back until none were able to fight . At the end of day , Castelnuovo was in Ottoman hands . Aftermath . Almost all of the Janissaries and 16 , 000 of other Ottoman units were killed in the assault . According to rumor , Turkish losses amounted to 37 , 000 dead . Of the Spanish troops only 200 survived , most of them wounded . One of the prisoners was the Biscayan Captain Machín de Munguía . Barbarossa , upon learning this , offered Munguía freedom and a place in his army . The admiral greatly admired him for his actions in the battle of Preveza , where the Spaniard had successfully defended a sinking Venetian carrack against several Ottoman warships . Munguía refused to accept and was therefore beheaded on the spur of the admiral ' s galley . Half of the prisoners and all the clerics were also slaughtered to satisfy the Ottoman soldiers , who were angry at the great losses which they had suffered in capturing the city . The few survivors were taken as slaves to Constantinople . Twenty - five of them managed to escape from prison six years later and sailed to the port of Messina . Despite the failure of Sarmiento to retain the fortress , Castelnuovo ' s defense was sung by numerous contemporaneous poets and praised all over Christian Europe . The Spanish soldiers who participated in the unequal engagement were compared with mythological and classical history heroes , being considered immortal due the magnitude of their feat . Only the enemies of Charles V , such as the Paduan humanist Sperone Speroni , rejoiced at the annihilation of the Tercio of Castelnuovo . The siege of Castelnuovo ended the failed campaign of the Holy League against the power of the Ottoman Empire in the Eastern Mediterranean . Charles V began negotiations with Barbarossa to attract him to the imperial ranks but got nothing and turned all its efforts in a great expedition against Algiers to destroy the Ottoman sea power . This expedition , known as the Journey of Algiers , ended in a disaster as a storm scattered the fleet and the army had to be reembarked having suffered heavy losses . A truce between Charles V and Suleiman the Magnificent was signed in 1543 . Castelnuovo remained in Ottoman hands for almost 150 years . It was recovered in 1687 , during the Morean War , by the Venetian Captain - General at sea Girolamo Cornaro , who in alliance with Montenegrins under Vuceta Bogdanovic , won a great victory over the Turks near the town and put the fortress under Venetian rule .