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The two most famous military orders to emerge from the Crusades were the Knights Templar, which was named for its first headquarters on the Temple Mount in Jerusalem, and the Knights Hospitaller, which ran a hospital in Crusader Jerusalem before it diversified into the fighting business. The Templars are easily the more famous of the two, since they've seeped well into popular literature and film (The Da Vinci Code, for example). But whereas the Templars were hunted down and disbanded in the early 1300s, the Hospitallers have survived to the present day—though now they're called the “Sovereign Military Order of Malta,” partly because of the siege we're about to revisit.
After the last of the Crusader states in the Levant, Acre, was captured by the Mamluks in 1291, the Hospitallers, also known as the Order of the Knights of St. John, went first to Cyprus and then to the Island of Rhodes.
Rhodes (Google Maps)
The Hospitallers conquered Rhodes in 1309 and ruled it as their own fiefdom—under the nominal suzerainty of the Byzantine Emperor—until 1522, when a massive Ottoman army drove them off the island after a six month siege. The surviving members of the order eventually wound up in Sicily, which was controlled by Charles I of Spain. Charles made the Knights his vassals and gave them the archipelago of Malta.
(“Malta” refers both to the archipelago nation and to the largest island in the archipelago. Fortunately all of the action in this 1565 siege takes place on the island of Malta, which simplifies things for the purposes of this essay.)
Malta (Google Maps)
As you can see, Malta (the archipelago and the island) is in a pretty strategic location, from which a powerful navy could control the chokepoint between the eastern and western halves of the Mediterranean and could disrupt the Ottoman-aligned Barbary Corsairs that sailed out of North Africa with the intention of making life miserable for Christian ships. This location made it an Ottoman target. The Hospitallers knew the danger this entailed, and it appears that they only accepted Charles's offer of the island because they really had nowhere else to go. They set to work garrisoning the island both to use as a naval base and in preparation for the Ottoman invasion they were pretty sure would be coming at some point.
However, when that invasion finally did arrive, in 1551, it came in the form of a small (maybe 10,000 men) Ottoman army that was nowhere near up to the task of besieging Malta's Saint Angelo Fort. After that siege failed the Ottomans did successfully loot the citadel on the island of Gozo, the second-largest of the Maltese islands, but that was just a consolation prize. Still, the Hospitallers and their Grand Master, Juan de Homedes (d. 1553), knew that a stronger Ottoman invasion was likely in the near future, and they set to work constructing two more forts on the island, Fort Saint Michael and Fort Saint Elmo. In 1560, a joint Spanish-Genoese-Venetian-Papal-Maltese fleet was resoundingly defeated by the Ottomans at Djerba, off the coast of southern Tunisia, and with Ottoman naval supremacy in the region assured, the time seemed right for another try at taking Malta.
So, on May 18, 1565, an Ottoman force of somewhere between 20,000 and 50,000 men came ashore on Malta and set to work besieging the Hospitallers, who numbered around 9000 and were now led by Jean Parisot de Valette (d. 1568). De Valette had been elected Grand Master in 1557 and was about 70 years old in 1565, but could still handle himself in a fight and was very much an active participant in the defense. The Ottoman force was led by...ah, well, it's complicated. The Ottoman sultan, Sulayman, in one of his less magnificent decisions, had for some reason divided command of the expedition, putting Lala Mustafa Pasha in command of the army and Piyale Pasha (the victor at Djerba) in command of the navy, but subordinating both to the Greco-Ottoman privateer Dragut, who was based out of Tunisia and was one of the great corsair captains (he was a pirate, in other words) of the age.
The siege lasted almost four months, so I'll spare you the nitty-gritty details. The Ottomans captured Fort Saint Elmo on June 23, but in the process lost 6000 soldiers, including Dragut. This deprived the expedition of its overall leader and left Piayle Pasha and Lala Mustafa Pasha in joint command, which doesn’t appear to have worked out so well from a cohesion standpoint. The Hospitallers were engaged in a holding action, waiting for reinforcements to arrive from Sicily, and so they gave ground grudgingly and tenaciously held on to Saint Elmo well after it became clear that the fort would inevitably fall—inflicting extra casualties on the Ottomans in the process.
Malta in some detail; the siege takes place in the area around Valletta (Wikimedia Commons)
This map, in conjunction with the one above, should give you some sense of where these forts were on the island (Wikimedia Commons)
The Ottomans besieged the two remaining fortresses, Saint Michael and Saint Angelo, but made very little progress throughout July and into August. By that point the besieging army was beginning to panic. They’d sustained heavy losses, both in combat and due to disease (often the real killer during extended sieges), against a numerically inferior force, and they had almost nothing to show for it. At some point the defense of Saint Michael appeared hopeless and the Hospitaller Council of Elders voted to evacuate and try to hold on to Saint Angelo until relief arrived, but de Vallette, guessing that the Ottomans were faltering, countermanded the council's decision and ordered Saint Michael to hold out as long as it could.
With winter approaching, the Ottomans looked for a place to settle in on the island but found nothing, and so they began preparing to board their ships and get the hell out of there. It was at this point that the long-promised relief from Sicily finally arrived, on September 7. That army arrived to find the Ottomans already retreating, and so it did little more than chasing the invaders back to their ships, which then disembarked for Istanbul on September 11.
19th century French painter Charles-Philippe Larivière’s Lifting of the Siege of Malta (Wikimedia Commons)
Historians disagree about the impact of the Ottoman failure at Malta. The narrative for a long time was that the Maltese victory had saved Christendom from an Ottoman onslaught in the western Mediterranean. But based on how poorly the Ottomans performed during the siege, and then at the Battle of Lepanto six years later, in hindsight it seems that the Ottomans were hitting an imperial plateau, and it's unclear whether they would have been able to hold on to Malta if they had managed to take it. For the Christians, Malta was a heroic victory but not a decisive one. The Ottomans may have been approaching the end of their peak, but they were still a great power and would remain so for at least another century. Still, the Hospitallers’ brave defense of Malta against such great odds became a rallying point for Christendom, and in that sense its impact may not be easily measured.