Ten of the Longest Sieges In the History of The World

While living in lockdown, most people have compared their restricted lives to those of people in a besieged city. The Idea of a city under siege is chilling. The sound of explosions against the city walls and regular news of unlucky escapees getting caught served to lengthen the days. As time passed, the food reserves in the city would reduce, hunger would ravage the inhabitants, and with that, desperation. Well, that is based on the legendary siege of troy, which may or may not have happened, but it gave us the word trojan horse. The bravery of a small city standing up to the advance of a powerful army are always interesting, though, which is why these 10 are unforgettable.


The Siege of Gibraltar

Gibraltar: 4 Years

Britain captured many overseas colonies from the Spanish and the French, but none was more humiliating than the 1704 capture of Gibraltar. It gave Britain easy access to the Mediterranean, which is why there was always an uneasiness around the coastal haven. When the American War of Independence began in 1775, the Spanish decided to take their piece of coast, and the French followed right behind. The Spanish came in with a force of 14,000 men and 11 ships in February 1778, but they couldn’t defeat the 5,000-man strong defence led by General George Elliot.

When the French joined them in 1779, the naval attacks of the besiegers grew stronger, but they suffered heavy losses during the grand assault launched in 1782 by 60,000 Franco-Spanish troops backed by 49 ships. With losses mounting, came humiliation. Frequent sneaking of supplies by the British Navy past the blockade only helped to strengthen the defenders. French reinforcements abandoned the war due to the embarrassment. The weakened Spanish forces negotiated an uneasy peace in 1783. The battle was the most significant show of force by Britain after losing control of America. It also went down as the longest continuous siege ever sustained by the British Army.

The Siege of Xiangyang

Xiangyang: 6 Years

Kublai Khan, the grandson of Genghis Khan, did the only thing his father didn’t do; Conquer China. China, with a population of nearly 100 million people in the 13th century, didn’t expect the Mongols to breach their walls. Xiangyang to the south was Kublai’s entry point, but as you would expect, breaching the great wall of china with swords, spears, and shields wasn’t easy.

There was a 5-year standoff as attacks by the Mongols against the wall were futile, while a similar fate met escape attempts by the Chinese. Kublai then called on his relatives in Europe, who were experts at breaching tough walls to help him breach Xiangyang. Two Persian Engineers helped Kublai build catapults, which acted as missile launchers that he used to fell towers and part of the wall giving way to the first ruling of China by a foreigner.

The Siege of Tripoli

Tripoli: 7 Years

The Lebanese city of Tripoli is not so popular in the modern world, but it was the centre of attraction in the 11th century after the first crusade. The besieger, in this case, was the stubborn crusader Raymond of Toulouse. He refused to go home after his defeat during the second crusade and instead decided to create the fourth crusade state like the Kingdom Of Jerusalem. However, after his defeat at the hands of the Seljuk Turks in Anatolia, Raymond only had 300 men left, and the leader of Tripoli wasn’t as welcoming as the previous leaders who were afraid of the crusaders.

The first war ended with Tripoli losing 7,000 men and the crusaders taking control of Tortosa, which they used to build the Fortress of Saint Gilles, cutting Tripoli’s land access. Tripoli stood through the siege from 1102 to 1109. The wars were deadly as the sides fought from time to time with Raymond trying to come in and the citizens trying to get out. It led to the death of Raymond himself in 1104 after being injured in an attempt to breach the city walls. The blockade led to the depletion of food, and people started fleeing. The nobles, tired of the suffering, later betrayed the city’s defences to the crusaders leading to its fall in 1109, during which the betrayers were also executed.

The Siege of Harlech Castle

Harlech Castle: 7 Years

This was one of the most interesting battles in British history when 50 men resisted an entire army for seven years. It happened between 1461 and 1468 during the Wars Of The Roses. In 1461, after winning the war of Towtown, King Edward IV put Lord Herbert in charge of the army to pursue Pembroke and the other Lancasterian lords. All Lancaster castles had fallen by 1462, but Harlech didn’t yield.

The castle defence was being led by a veteran soldier David Einion who had fought in the 100 years war and hence understood how to withstand a siege. Harlech also had direct access to the coast allowing the Lancastrians to sneak in supplies right under the siege. The castle held until 1468 when King Edward himself raised an army of 10,000 and took the castle. It is the longest siege in British history.

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The Siege of Thessalonica

Thessalonica: 8 Years

The Ottomans ruled Thessalonica until 1912, nearly 500 years after spending eight years to retake the city from the Palaigoloi Dynasty of the Byzantine empire in 1431. The siege started when General Murad II of the Ottomans laid a naval blockade on the city in 1423 as punishment to the dynasty for inciting violence in Ottoman cities. The Palaigoloi ruler, Andronikos, then handed the city over to Venice, preferring the Venetians to take the city rather than the Ottomans. The Ottoman siege was tight, and naval access to Thessalonica was cut off, leading to starvation in the city. There were regular attacks on the defences, but they were not strong enough to defeat the Venetians.

Venice also couldn’t afford to put a big defence in the city because Murad was attacking them on other fronts at the same time. Defending Thessalonica proved too expensive for Venice, which is why Murad pillaged the city with ease in 1431 when he finally brought his mighty forces to Macedonia. More than 10,000 residents were taken as slaves while the rest fled the city.

The Siege of Drepana
The Siege of Drepana

Drepana: 8 Years

The taking of Drepana was significant in the rise of the Roman Empire into a world power as it gave them full control of the key trade route across the Mediterranean. It started in 249 BC when the Roman Council Claudius Pulcher placed land and naval blockade on Sicily, making it the first naval siege of the Punic Wars. The Carthaginians were better at naval combat than the Romans, which is why the siege was easily trespassed by Carthaginian ships.

The Roman land army was solid and managed to blockade Drepanium throughout the siege until 241 when the Romans finally gained the victory. The naval front was, however, a disaster for the Romans as fleet after fleet got destroyed by the Sicilian Navy and storms. The Romans finally managed to take control of the city and establish their power over Sicily and Spain after reconstructing their fleet under Gaius Lutatius Catulus in 241.

The Siege of Solovetsky Monastery

Solovetsky Monastery: 8 Years

The centralization of the Russian Orthodox church under the control of the government wasn’t supported by all believers. The greatest resistance came from the Solovetsky Monastery, which was home to over 500 monks and priests as well as workers and some peasants. Runaway soldiers and peasants also joined the monks on the island. The Tsar, Patriarch Nikon of Moscow, sent an army to quash the resistance in 1668, but the stubborn monks locked the doors to the heavily fortified monastery.

Despite the little armed resistance, the monastery proved impregnable for the troops. The monks, who enjoyed the support of the local peasants, continued to receive food donations and supplies through secret routes. Support for the old believers, as they were called, only continued to mount into the 1670s as more people sneaked in to build more fortifications for the fortress. In 1676, one monk betrayed his brothers by giving the forces the details to a secret entrance leading to a bloody massacre of the unrelenting monks.

The Siege of Ishiyama Honganji

Ishiyama Honganji: 11 Years

Starvation always proves the best method of ending a siege, and that is exactly what Oda Nobunaga did when he captured Ishiyama Hongan-Ji, a former Buddhist spiritual centre. The conquest was important for Nobunaga to gain full control of Osaka, but it meant fighting past a group of Jodo Shinshu monks and Ikko-Ikki peasants, both of whom were opposed to Nobunaga’s mission. The resistance was fierce as the warrior-monks, and the peasants stood up to the 30,000-man blockade repelling attacks and sneaking supplies into the monasteries and castles around the city under Nobunaga’s forces.

The resistance which started in 1570 became unsustainable in the late 70s when Nobunaga finally figured out most of the routes that the peasants used to supply the city and escape the blockade. Starvation forced the monks to burn down the Ishiyama monastery and most of the settlements in the city before surrendering to Nobunaga in 1580.

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The Siege of Philadelphia

Philadelphia: 12 Years

This was another endless standoff between the Ottomans and the Byzantine empire. Philadelphia was another Byzantine city in Asia Minor (now called Alaşehir), which came under constant attacks by the Ottomans. In 1373, the Byzantine Ruler Manuel II sold the city to the Ottomans after they helped him quash the 14th century Byzantium civil war. However, in 1378 when the Turks arrived to take control of the city, the leaders and the citizens closed the gates on them and retreated inside.

The walls had been strengthened after the previous Venetian control of the city, making it impossible for the besieging army to make their way in. The standoff continued for a whole 12 years as the city refused to heed calls by the Byzantine king to give up the resistance. The Ottomans were forced to negotiate with the city’s leaders on their own terms in 1790 after 12 years of an embarrassing blockade.

The Siege of Candia

Candia: 25 Years

The 25-Year blockade of the city of Candia remains the longest siege in known history. The siege was so long that the soldiers that fought towards its end were children born during the siege itself. Candia was the capital of the foreign territory of Venice off the coast of Greece. The group of Islands remained under the control of Venice after the Ottomans conquered most of the surrounding territories, and the Ottomans always looked for an excuse to attack the Islands. The provocation came in 1644 when soldiers from Malta attacked an Ottoman convoy headed to Mecca and landed in Candia. Instead of the Ottomans taking their revenge to Malta, they headed straight for Candia, overran the surrounding Islands before landing on Candia in 1645. The 60,000-man army took two months to lay siege on the city.

The Canadians also took the same period to stock up and strengthen the city defences and so the stalemate began. While the Ottomans surrounded Crete, the Venetians instituted a blockade on supplies to the Ottoman forces from surrounding islands and sneaked in supplies to Candia through secret routes. It soon became a double blockade, with Candia under siege and the besiegers besieged as well.
The French forces and other Western European states joined to support Venice in defending Candia, but the Ottomans had strong naval and land defences leading to a huge loss of lives on both sides. In 1668, the French abandoned their positions, leaving only 3,600 Candian defenders who, in turn, negotiated a treaty with the Ottomans. All Christians were allowed to get out of Candia before the Ottomans took control of it.

Author: Gus Barge

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