Sinan -The Great Jewish Pirate

by Gideon

Sinan was born in 1492 in Spain. He died in 1546 in the Ottoman Empire where he riched the rank Rank of Admiral of the fleet. Sinan was also known as the The Great Jew, Sinan the Chief, The Famous Jewish Pirate, and Sinan the Jew.


In response to the Spanish Expulsion and to the terror that the Spanish inquisition inflicted on Jews who converted to Christianity and were suspected of practicing Judaism in hiding, Jews fought back. In most cases they did it indirectly by continuing to practice their religion in secrecy, by using their wealth to finance military campaigns against the Spanish Empire, and by reporting the movements of Spanish ships.  There were Jews who took advantage of their ability communicate with other Jews worldwide through routine commercial activities to report to Spain’s enemies the locations and routes of Spanish ships carrying treasures from the New World to Spain. Few Jews fought directly against the Spanish Empire as Pirates, mostly in the Caribbean Sea. One of those sea warriors was Sinan, Barbarossa’s second in command. Barbarossa was the Ottoman naval commander. Barbarossa and Sinan operated in the Mediterranean Sea. Sinan was referred to in Crown correspondence with England’s Henry VII as “the  Great Jewish Pirate”.

In his book, Jewish Pirates of the Caribbean, Edward Kritzler wrote that “While Barbarossa name was feared throughout Christendom, he was not really a naval commander or even much of a sailor. Instead he occupied himself with building his navy and plotting its moves and left most of the sea battles to his favored captain, Sinan, a Jewish refugee from Spain via Turkey.”

This is the story of  how Barbarossa and Sinan broke the back of the Spanish armada in the Mediterranean Sea.

Spain Expulsion and the Spanish Inquisition

In 1492, Ferdinand and Isabella, the Spanish monarchs, issued the edict that all Jews should be driven out of the kingdom and its territories. On July 30 of that year, the entire Jewish community, some 200,000 people, were expelled from Spain. In the last days before the expulsion, rumors spread throughout Spain that the fleeing refugees had swallowed gold and diamonds, and many Jews were knifed to death by robbers hoping to find treasures in their stomachs. Tens of thousands of refugees died while trying to reach safety. In some instances, Spanish ship captains charged Jewish passengers exorbitant sums, then dumped them overboard in the middle of the ocean.

This was the end of 1,500 hundreds years of Jewish continues presence in Spain. A place they called home long before Christianity. At the peak of the Jewish presence in Spain, the Jewish community numbered about half a million people. About 100,000 Jews were murdered and about 200,000 Jews were forced to become Christians in the the century prior to the expulsion. The remaining 200,000 Jews who refused to convert were forced to leave Spain. 

The most fortunate of the expelled Jews succeeded in escaping to Turkey. Sultan Bajazet welcomed them warmly. “How can you call Ferdinand of Aragon a wise king,” he was fond of asking, “the same Ferdinand who impoverished his own land and enriched ours?” Among the most unfortunate refugees were those who fled to neighboring Portugal. In 1496, King Manuel of Portugal concluded an agreement to marry Isabella, the daughter of Spain’s monarchs. As a condition of the marriage, the Spanish royal family insisted that Portugal expel her Jews. King Manuel agreed, although he was reluctant to lose his affluent and accomplished Jewish community. In the end, only eight Portuguese Jews were actually expelled; tens of thousands of others were forcibly converted to Christianity on pain of death. The chief rabbi, Simon Maimi, was one of those who refused to convert. He was kept buried in earth up to his neck for seven days until he died.

The Spanish Jews who ended up in Turkey, North Africa, Italy, and elsewhere throughout Europe and the Arab world, were known as Sephardim— Sefarad being the Hebrew name for Spain. After the expulsion, the Sephardim imposed an informal ban forbidding Jews from ever again living in Spain. Specifically because their earlier sojourn in that country had been so happy, the Jews regarded the expulsion as a terrible betrayal, and have remembered it ever since with particular bitterness. Of the dozens of expulsions directed against Jews throughout their history, the one from Spain remains the most infamous.

The Spanish Inquisition operated “in Spain and in all Spanish colonies and territories, which included the Canary Islands, the Spanish Netherlands, the Kingdom of Naples, and all Spanish possessions in North, Central, and South America.” The inquisition was intended primarily to ensure the orthodoxy of those who converted from Judaism and Islam. The regulation of the faith of the newly converted was intensified after the royal decrees issued in 1492 and 1502 ordering Jews and Muslims to convert or leave Spain. In 1483, Ferdinand and Isabella established a state council to administer the inquisition with the Dominican Friar Tomás de Torquemada acting as its president, even though Sixtus IV protested the activities of the inquisition in Aragon and its treatment of the conversos. Torquemada eventually assumed the title of Inquisitor-General. The conversos  were the principal concern of the inquisition; being suspected of continuing to practice Judaism put them at risk of denunciation and trial. Torquemada established a new court that announced with a thirty-day grace period for confessions and the gathering of accusations by neighbors. Evidence that was used to identify a crypto-Jew included the absence of chimney smoke on Saturdays (a sign the family might secretly be honoring the Sabbath) or the buying of many vegetables before Passover or the purchase of meat from a converted butcher. The court employed physical torture to extract confessions. Crypto-Jews were allowed to confess and do penance, although those who relapsed were burned at the stake. The most intense period of persecution of conversos lasted until 1530. It is unknown exactly how many people were tortured and killed, or how much wealth was confiscated from converted Jews and others who were  tried by the Inquisition.

Jews in the Ottoman Empire in the 16th Century

The Ottomans began to emerge as a great political and military power from the early 14th century. Uthman, founder of a dynasty, came from a small Turkish principality, which in time grew into a vast empire. The swords of his successors brought to an end the centuries‑long Greek influence in the south of the Mediterranean basin, replacing it with Muslim domination. Extending deep into the European continent, Ottoman expansion turned Vienna into an outpost of Christendom.

In the wake of the expulsion from Spain (1492) and the forced conversion in Portugal (1497), tens of thousands of Iberian Jews arrived in Ottoman territories. As all that was required of them was the payment of a poll‑tax and acknowledgement of’ the superiority of Islam, the empire became a haven for these refugees.

From early in the 16th century, the Jewish community in the Ottoman Empire became largest in the world. Constantinople and Salonika each had a community of approximately 20,000 people. Immigration from the Iberian peninsula, arriving in several waves throughout the 16th century. After the conquest of Constantinople, Muhammad II, wishing to aggrandize the city and make it into a capital, brought into it many people from the provinces.

Throughout the 16th century, the Jews in the Ottoman Empire enjoyed remarkable prosperity. The empire was rapidly expanding, and economic demand rose accordingly. Thus the Jewish population could easily enter into trade with Christian Europe, and into industries such as wool weaving that were only then beginning to evolve. Under the leadership of figures like Don Joseph Nasi and Solomon ibn Yaish, they could take advantage of their worldwide network of family connections and their knowledge of European affairs in order to promote the concerns of the Sublime Porte, as well as to protect their personal interests and those of their community.

Suleiman the Magnificent

Suleiman the Magnificent became a prominent monarch of 16th-century Europe, presiding over the apex of the Ottoman Empire’s economic, military and political power. Suleiman personally led Ottoman armies in conquering the Christian strongholds of Belgrade and Rhodes as well as most of Hungary before his conquests were checked at the Siege of Vienna in 1529. He annexed much of the Middle East in his conflict with the Safavids and large areas of North Africa as far west as Algeria. Under his rule, the Ottoman fleet dominated the seas from the Mediterranean to the Red Sea and through the Persian Gulf. Suleiman the Magnificent was the tenth and longest-reigning sultan of the Ottoman Empire from 1520 to his death in 1566. Under his administration, the Ottoman state ruled over 15 to 25 million people. Suleiman in his time was regarded as the most significant ruler in the world, by both Muslims and Europeans. The Europeans called him “The Magnificent,” but the Ottomans called him Kanuni, or “The Lawgiver.” The primacy of Suleiman as a law-giver is at the foundation of his place in Islamic history and world view.

His military empire expanded greatly both to the east and west, and he threatened to overrun the heart of Europe itself. In Constantinople, he embarked on vast cultural and architectural projects. Istanbul in the middle of the sixteenth century was architecturally the most energetic and innovative city in the world. While he was a brilliant military strategist and canny politician, he was also a cultivator of the arts. Suleiman’s poetry is among the best poetry in Islam, and he sponsored an army of artists, religious thinkers, and philosophers that outshone the most educated courts of Europe.

In the sixteenth century, the leading financiers in Istanbul were Greeks and Jews. Many of the Jewish financiers were originally from Iberia and had fled during the period leading up to the expulsion of Jews from Spain. Many of these families brought great fortunes with them. The most notable of the Jewish banking families in the 16th-century Ottoman Empire was the Marrano banking house of Mendès, which moved to and settled in Istanbul in 1552 under the protection of sultan Suleiman I the Magnificent. 

Having consolidated his conquests on land, Suleiman was greeted with the news that the fortress of Koroni in Morea (the modern Peloponnese, peninsular Greece) had been lost to Charles V’s admiral, Andrea Doria. The presence of the Spanish in the Eastern Mediterranean concerned Suleiman, who saw it as an early indication of Charles V’s intention to rival Ottoman dominance in the region. Recognizing the need to reassert naval preeminence in the Mediterranean, Suleiman appointed an exceptional naval commander in the form of Khair ad Din, known to Europeans as Barbarossa. Once appointed admiral-in-chief, Barbarossa was charged with rebuilding the Ottoman fleet, to such an extent that the Ottoman navy equaled in number those of all other Mediterranean countries put together.

Charles V, Holy Roman Emperor

Charles V was born 20 February 1500, at Ghent (now Belgium), and spent his youth in the Netherlands. Since his father, Philip of Burgundy, died in 1506, and his mother Joanna (third child of Ferdinand of Aragon and Isabella of Castile) suffered from a clouded intellect, he succeeded to the Netherlands possessions and to the county of Burgundy, and after Ferdinand’s death also to the Spanish lands. Charles V was the ruler of both the Spanish Empire from 1516 and the Holy Roman Empire from 1519, as well as of the Habsburg Netherlands from 1506. Through inheritance, he brought together under his rule extensive territories in western, central, and southern Europe, and the Spanish colonies in the Americas and Asia. As a result, his domains spanned nearly four million square kilometers and were the first to be described as “the empire on which the sun never sets”.

Spain was the core of Charles V personal possessions. It was also his most important military asset, as it provided a great number of generals, as well as the formidable Spanish tercios, considered the best infantry of its time. Charles controlled a large amount of land in Europe, as well as the newly acquired lands of the Americas to which Spain claimed much and began to possess more of throughout his reign. But Charles placed more importance upon Spain than his other lands. The “Golden Age” Spain of Ferdinand and Isabella became his own as Charles made it his base of power and his home throughout his long reign. His reign was dominated by war, and particularly by three major simultaneous conflicts: the Habsburg-Valois Wars with France, the struggle to halt the Ottoman advance, and the Protestant Reformation resulting in conflict with the German princes. France’s King Francis I and Suleiman the Magnificent were allied in their war against Charles V. Francis was backing border raids into Italy,  while 100,000 of Suleiman’s horsemen massed on the eastern bank of the Danube waiting for their opportunity to invade Charles’ empire.

The struggle with the Ottoman Empire was fought in Hungary and the Mediterranean. After seizing most of eastern and central Hungary in 1526, the Ottomans’ advance was halted at their failed Siege of Vienna in 1529. A lengthy war of attrition, conducted on his behalf by his younger brother Ferdinand, continued for the rest of Charles’s reign. In the Mediterranean, although there were some successes, Charles was unable to prevent the Ottomans’ increasing naval dominance and the piratical activity of the Barbary Corsairs.

 It is not clear to what extent Charles protected Jews and conversos in his empire. Some sources describe him as a “Jewish Hero” for standing by the Jews. Other sources describe him as a ruler who allowed Jews and conversos to conduct business despite the inquisition’s will when it served his purposes and brought him much needed money to finance his wars. Then, he allowed the inquisition to arrest the Jews and the conversos, strip them of their wealth, and murder them. One fact is undisturbed; many Jews and conversos were tortured and murdered in his vast empire, while he was in power.


Khair-ed-Din, known to Christians as Barbarossa for his red beard, was born on the Ottoman island of Lesbos, now part of Greece. He was the son a converted Turk of Albanian origin from Greece, and an Orthodox Christian, Greek woman from Lesbos. His mother was a widow of a Greek Orthodox priest. His parents were married and had two daughters and four sons. Ishak, Oruç, Khair and Ilyas. His father took part in the Ottoman conquest of Lesbos in 1462 from the Genoese Gattilusio dynasty and as a reward, was granted the fief of the Bonova village in the island. He became an established potter and purchased a boat to trade his products. The four sons helped their father with his business. 

The brothers initially worked as sailors, but then turned privateers in the Mediterranean to counteract the privateering of the Knights Hospitaller (Knights of St. John) who were based in the island of Rhodes (until 1522). Oruç and Ilyas operated in the Levant, between Anatolia, Syria, and Egypt. Khair operated in the Aegean Sea and based his operations mostly in Thessaloniki. Ishak, the eldest, remained on Mytilene and was involved with the financial affairs of the family business. Oruç was a very successful seaman. He also learned to speak Italian, Spanish, French, Greek and Arabic in the early years of his career. While returning from a trading expedition in Tripoli, Lebanon, with his younger brother Ilyas, they were attacked by the Knights of St. John. Ilyas was killed in the fight, and Oruç was wounded. Their father’s boat was captured, and Oruç was taken as a prisoner and detained in the Knights’ castle at Bodrum for nearly three years. Upon learning the location of his brother, Khair went to Bodrum and managed to help Oruç escape.

 Oruç later went to Antalya, where he was given 18 galleys by the Şehzade Korkut, an Ottoman prince and governor of the city, and charged with fighting against the Knights of St. John, who were inflicting serious damage on Ottoman shipping and trade. In the following years, when Korkut became governor of Manisa, he gave Oruç a larger fleet of 24 galleys at the port of İzmir and ordered him to participate in the Ottoman naval expedition to Apulia in Italy, where Oruç bombarded several coastal castles and captured two ships. Between 1503 and 1516 the brothers raided numerous Spanish ports and captured many Spanish ships. In 1516, the three brothers succeeded in capturing Jijel and Algiers from the Spaniards but eventually assumed control over the city and surrounding region, forcing the previous ruler, Abu Hamo Musa III of the Beni Ziyad dynasty, to flee. The Spaniards in Algiers sought refuge on the island of Peñón off the Moroccan coast and asked Charles V, King of Spain and Holy Roman Emperor, to intervene, but the Spanish fleet failed to force the brothers out of Algiers. After consolidating his power and declaring himself Sultan of Algiers, Oruç sought to enhance his territory inland and took Miliana, Medea and Ténès. He became known for attaching sails to cannons for transport through the deserts of North Africa.

In 1517, the brothers raided Capo Limiti and later, the Island of Capo Rizzuto in Calabria. For Oruç, the best protection against Spain was to join the Ottoman Empire, his homeland and Spain’s main rival. For this, he had to relinquish his title of Sultan of Algiers to the Ottomans. He did this in 1517 and offered Algiers to the Ottoman Sultan Selim I. The Sultan accepted Algiers as an Ottoman sanjak (“province”), appointed Oruç as the Governor of Algiers and Chief Sea Governor of the West Mediterranean, and promised to support him with janissaries, galleys and cannons. In May 1518, Emperor Charles V arrived at Oran and was received at the port by Sheikh Buhammud and the Spanish governor of the city, Diego de Córdoba, marquess of Comares, who commanded a force of 10,000 Spanish soldiers. Joined by thousands of local Bedouins, the Spaniards marched overland towards Tlemcen. Oruç and Ishak awaited them in the city with 1,500 Turkish and 5,000 Moorish soldiers. They defended Tlemcen for 20 days, but were eventually killed in combat by the forces of Garcia de Tineo. 

Khair, now given the title of Beylerbey by Sultan Selim I, along with janissaries, galleys and cannons, inherited his brother’s place, his name (Barbarossa) and his mission.

Barbarossa’s flag:

Sinan the Pirate

After being forced out of Spain, Sinan’s family relocated to Smyrna,Turkey, his birthplace. As a young man carrying the wounded pride of his displaced family, Sinan joined forces with the Ottoman Empire and with Barbary Coast buccaneers that savaged the navies of Spain’s Charles V, the Holy Roman Emperor. Endearing himself to the famous Ottoman admiral Barbarossa, Sinao O Judeo, as the Portuguese called him, led the Ottoman’s to victory over the Spanish through cunning and often brilliant military strategy. 

On August 20,1534, Sinan led a hundred ships into the harbor of the North African city Tunis which was the property of Charles V. With this capture, Suleiman the Magnificent controlled the entire Mediterranean  Sea. Charles’ ships could no longer find a safe harbor in the Mediterranean Sea outside Spain’s waters. Charles first attempted to convince Barbarossa to  switch sides, but when it didn’t work, in 1935, he led an  armada of 400 ships and 30,000 soldiers to fee Tunis. Barbarossa assigned the defense of the city to Sinan and 5,000 of his best men. Charles bombarded the fort with cannon from 70 ships. For 24 days, Sinan and his men held out. Three times Sinan sailed to battle the Spanish armada, but the odds were against him. When the fort’s walls collapsed under the constant bombardment, Spanish, German, and Italian forces poured into the fort. Sinan and the remaining of his men crossed the bay to the city. The next day when Charles and his army fought their way into the city, Barabarosa, Sinan, and 4,000 of their men escaped the city on camels heading to the desert to fight another day. For three days, Charles soldiers slaughtered 70,000 innocent people, who until a yer before were Charles’ subjects. 40,000 people were taken prisoners. It was called the worst carnage of the century in Catholic chronicles. 

In 1536, Barbarossa was called back to Istanbul to take command of 200 ships in a naval attack on the Habsburg Kingdom of Naples. In July 1537, he landed at Otranto and captured the city, as well as the Fortress of Castro and the city of Ugento in Apulia. In August 1537, Lütfi Pasha and Barbarossa led a huge Ottoman force that captured the Aegean and Ionian islands belonging to the Republic of Venice, namely Syros, Aegina, Ios, Paros, Tinos, Karpathos, Kasos, Kythira, and Naxos. In the same year, Barbarossa raided Corfu and obliterated the agricultural cultivations of the island while enslaving nearly all the population of the countryside. However, the Old Fortress of Corfu was well defended by a 4,000-strong Venetian garrison with 700 guns, and when several assaults failed to capture the fortifications, the Turks reluctantly re-embarked and once again raided Calabria. These losses caused Venice to ask Pope Paul III to organize a “Holy League” against the Ottomans.

In February 1538, Pope Paul III succeeded in assembling a Holy League (composed of the Papacy, Spain, the Holy Roman Empire, the Republic of Venice and the Maltese Knights) against the Ottomans, commanded by Andrea Doria. But Barbarossa’s forces led by Sinan operating out of Algiers destroyed most of Spain’s naval fleet off the port of Pleveza, in Greece.  Sinan led his ships under the flag of the Seal of Solomon, similar in appearance to the Star of David.This victory secured Ottoman dominance over the Mediterranean Sea for the next 33 years, until the Battle of Lepanto in 1571.

In the following year, Sinan blocked the Gulf of Cattaro on the dalmation coast and forced the surrender of the last Spanish garrison. In 1540, Emperor Charles’ forces captured Sinan’s son and had him baptized by the Lord of Elba. In 1543, Charles attempted to capture the Algiers. He sailed with a force of 50 warships, 200 support vessels, and about 20,000 soldiers. They encountered bad weather on Algiers shores. Charles lost 14 warships and 100 transport vessels were destroyed. His soldiers were unable to get though the deep mud. Moorish horsemen charged down from the hills attacked his army  and he was forced to retreat.

In 1543, Barbarossa headed towards Marseilles to assist France, then an ally of the Ottoman Empire, and cruised the western Mediterranean with a fleet of 210 ships (70 galleys, 40 galliots and 100 other warships carrying 14,000 Turkish soldiers, thus an overall total of 30,000 Ottoman troops). On his way, while passing through the Strait of Messina, he asked Diego Gaetani, the governor of Reggio Calabria, to surrender his city. Gaetani responded with cannon fire, which killed three Turkish sailors. Barbarossa, angered by the response, besieged and captured the city. He then landed on the coasts of Campania and Lazio and, from the mouth of the Tiber, threatened Rome, but France intervened in favor of the pope’s city. Barbarossa then raided several Italian and Spanish islands and coastal settlements before laying the Siege of Nice and capturing the city on 5 August 1543 on behalf of the French king, Francis I. The Ottoman captain later landed at Antibes and the Île Sainte-Marguerite near Cannes before sacking the city of San Remo, other ports of Liguria, Monaco and La Turbie. He spent the winter with his fleet and 30,000 Turkish soldiers in Toulon, but occasionally sent his ships from there to bombard the coasts of Spain. The Christian population had been evacuated, and the Cathedral of St. Mary in Toulon was transformed into a mosque for the Turkish soldiers, while Ottoman money was accepted for transactions by the French tradesmen in the city.

In the spring of 1544, after assaulting San Remo for the second time and landing at Borghetto Santo Spirito and Ceriale, Barbarossa defeated another Spanish-Italian fleet and raided deeply into the Kingdom of Naples. After leaving Provence from the port of Île Sainte-Marguerite in May 1544, Barbarossa assaulted San Remo for the third time, and when he appeared before Vado Ligure, the Republic of Genoa sent him a substantial sum to save other Genoese cities from further attacks.

Sinan was in the Suez on the Red Sea, preparing an Indian force to attack the Portuguese. At the same time, Barbarossa was sailing near Elba. Barbarossa sent an envoy to bargain the return of Sinan’s son. After several failed negotiations for the boy’s release, Barbarossa’s landed his forces at Piombino. He ransacked the town and blew up the fort, releasing Sinan’s son. He then captured Castiglione della Pescaia, Talamone and Orbetello in the province of Grosseto in Tuscany. There, he destroyed the tomb and burned the remains of Bartolomeo Peretti, who had burned his father’s house in Mytilene the previous year, in 1543. He then captured Montiano and occupied Porto Ercole and the Isle of Giglio. He later assaulted Civitavecchia, but Leone Strozzi, the French envoy, convinced Barbarossa to lift the siege. 

The Ottoman fleet then assaulted the coasts of Sardinia before appearing at Ischia and landing there in July 1544, capturing the city as well as Forio and the Isle of Procida before threatening Pozzuoli. Encountering 30 galleys under Giannettino Doria, Barbarossa forced them to sail away towards Sicily and seek refuge in Messina. Due to strong winds, the Ottomans were unable to attack Salerno but managed to land at Cape Palinuro nearby. Barbarossa then entered the Strait of Messina and landed at Catona, Fiumara and Calanna near Reggio Calabria and later at Cariati and at Lipari, which was his final landing on the Italian peninsula. There, he bombarded the citadel for 15 days after the city refused to surrender and eventually captured it. He finally returned to Istanbul and, in 1545, left the city for his final naval expeditions, during which he bombarded the ports of the Spanish mainland and landed at Majorca and Minorca for the last time.

He then sailed back to Istanbul and built a palace on the Bosphorus, in the present-day quarter of Büyükdere in the Sarıyer district. Barbarossa retired in Istanbul in 1545, leaving his son Hasan Pasha as his successor in Algiers. He then dictated his memoirs to Sinan. They consist of five hand-written volumes known as Gazavat-ı Hayreddin Paşa (Conquests of Hayreddin Pasha). Today, they are exhibited at the Topkapı Palace and Istanbul University Library.

In 1551, Sinan captured Tripoli, occupied the port, and imprisoned the Knights of Malta. In May 1553, in his final recorded action Sinan sailed from Gallipoli with 150 ships. He ravaged the southern Italian coast and Sicily. He landed in Corsica, expelling the Genoese, and claimed Corsica on behalf of the king of France. He then returned to Constantinople.