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10 of the Longest Sieges in History

War is as old as man and sieges are one of the unavoidable outcomes of any conflict. Most people believe that the besieged army was always the loser, but this was only the case if the siege was a short one. Some stalemates went on for decades with whole generations born in fortresses never seeing peace for a better part of their lives. In such a case, it no longer mattered whether you were inside or outside the castle; everyone was a loser. These ten went down in history as the most extended standoffs that heeded to neither violence nor diplomacy.

The Siege of Candia – 21 Years

This siege was so expensive that its very cost nearly toppled both the Ottoman Empire and Venice. The Ottomans sought a way of taking control of the Candia, modern-day Heraklion, Greece, for a long time because Venice controlled critical Mediterranean trading routes that were key to the empire. The Ottoman advance on Venice was provoked by an attack on an ottoman ship headed for Constantinople. The early attacks saw the Ottoman army take control of many Islands controlled by Venice until 1648 when they finally arrived at the gates of Candia. Early attacks by the Ottomans were met by equal force from the Canadian protectors who killed tens of thousands of Ottoman soldiers that attempted to scale the walls.

The Ottomans however successfully cut off all supplies to Candia bringing the whole city to a standstill. To break the blockade, the Candian generals even considered weaponizing the plague and launching biological warfare on the Ottomans. The war however continued with all attacks from the ottomans repelled successfully. Several sneaky supplies and reinforcements from the French kept the Candian soldiers strong allowing them to hold off one of the greatest armies in the world at the time until 1649 when an agreement was struck to allow civilians to leave the city.[1][2]

The Siege of Gerdkuh – 17 Years

Nizari Ismaili was a powerful independent Shia power throughout Persia and Syria from 1090 when Hassan Sabah took control of the famous Alamut Castle. The state held several castles throughout the vast Persian empire in the face of hostile opposition for nearly two centuries until the Mongols under Genghis Khan’s grandson Helagu Han advanced on their fortresses. Gerdkuh which translates to the “the round mountain” was a strong castle surrounded by five forts which is why it was the last standing Fortress for the Shia empire. Helagu Han, armed with 5000 men advanced on the castle in 1253 bombarding it and launching ground assaults that were met by an equally ferocious resistance from the heavily guarded city, a surprising reaction considering the ferocity of Mongol attacks that were known to flatten entire cities. This standoff went on for 17 years, proving to be a nuisance to the fast advancing western Mongol empire. All the other castles had surrendered by 1270 when the Nizari commanders of Gerdkuh finally ran out of provisions and were forced to surrender to the mighty Mongols.[3][4]

The Siege of Philadelphia – 12 Years

This was the most significant battle in the fall of the Byzantine empire in Asia Minor. Philadelphia was a remotely located city in the province of Asia then controlled by the Byzantine Empire and even mentioned in the book of Revelation in the bible. The Ottomans had forced the Byzantine rulers to submission and even forced the emperor to accompany Ottoman Turks on expeditions to destroy Greek cities. Philadelphia was however well fortified and being remotely located; it managed to stay on as the last independent Byzantine state acting as a haven for early Christians. Although they were forced to pay a protection tax to several Ottoman militias from Anatolia and other neighboring states, they evaded the worst Ottoman attacks of the 13th century.

The Embarrassing standoff, however, came in 1379 when the Sultan asked Manuel II, the Byzantine emperor who was facing much resistance at the time to give up Philadelphia in exchange for support in the civil war. The people of Philadelphia dismissed the order and refused to give in even after their own king surrendered. There are few details on how the siege exactly went down, but the fact remains that the great Ottoman army was forced to stay outside the city walls for 12 years. By the late 1380s, the Sultan was getting restless because The war was getting expensive and embarrassing. The Ottomans summoned the two living Byzantine leaders at the time, John V and Manuel II and forced them to persuade their people to give up the city. The Ottomans finally took over Philadelphia after an agreement with the city rulers in 1390.[5][6]

The Siege of Troy – 10 Years

The Trojan war is told as both history and legend, and though there are few details oh how this bronze age war happened, Every historian agrees that it was fascinating. The whole disagreement started when Paris, a prince of Troy abducted Queen Helen of Sparta prompting her husband Menelaus King of Sparta to mobilize the entire Hellenic Fleet against Troy in 1250 BCE. Troy was well supplied and protected, but it had no chance against the thousands of Greek ships forcing the whole city to seek salvation behind the great walls. Trojans made several attempts to get supplies and reinforcements through underground tunnels, but the Greeks always found a way of stopping it. Eventually, the two armies were equally marched forcing everyone to keep to their side of the wall.

After 10 years of blockade, Trojans were weak and starved, and this is when the famous Greek war master Odysseus came up with the ultimate trick. He designed a plan for the Greeks to retreat partially leaving a wooden horse intended as a gift to fool the Trojans. Inside the wooden horse, Odysseus loaded grain as well as a group of soldiers that would attack Troy from within when the hungry Trojans took in the statue for the grain. Once inside, Greek soldiers attacked Troy and opened the gates for the rest of the army to come in laying waste to the great city of Troy.[7]

The Siege of Ishiyama Honganji – 11 Years

This siege was very significant to Japan as it went down in History as the strongest ever opposition to Oda Nobunaga. Oda Nobunaga unified most of Japan during the Sengoku period despite much opposition from other lords. Among his greatest opponents were the warrior monks of Ishiyama who were determined to keep the old religion against the great conquering power. Nobunaga attacked their monastery in late 1570 with a strong force of 30,000 armed men. The monks were about half that number of attackers, but their monastery was heavily guarded by a vast network of fortresses owned and patrolled by monks and supporters.

The excellent coordination of the monks who could respond to an attack in tens of thousands meant that every attack was repelled successfully. The fortress also had a continuous flow of supplies by sea because of the opposition to Nobunaga which had since turned to support the monks. By 1578, both Nobunaga and the monks had a series of victories and losses, but none had really managed to outwit the other. Nobunaga finally managed to starve the monks out after successfully blocking their naval supply networks. The monks however burnt down the monastery before surrendering in 1580 making it entirely worthless.[8]

The Siege of Slovetsky Monastery – 8 Years

This is another historical showdown between a church and a government and this time; it was just 500 monks standing up to the full force of Nikon, the seventh patriarch of Moscow. The group of monks, famously known as the old believers opposed the proposed unification of the Russian Orthodox church and locked themselves up inside their fortress on June 22nd, 1668 when the government sent a squad to put them in line. They did not confront the soldiers, but their impregnable walls just made it impossible for the soldiers to enter the monastery. They continued to build fortifications and relied on local farmers and peasants to sneak in food for them through the 8 years of the blockade. They were however betrayed by a monk called Feoktist in 1676 when he showed the soldiers an unmanned window that allowed them to march on the monastery. Of the 500 old believers in the Monastery, only 60 came out alive only to be executed later by the state.[9][10]

The Siege of Thessalonica – 8 Years

This was another face-off between Venice and the Ottomans, this time under Sultan Murad II. The Ottomans had subdued the Byzantine empire. In a bid to cause havoc in Ottoman ranks, The Palaiologoi dynasty attempted to incite rebellion, a move that angered the Sultan prompting him to lay a naval blockade on Thessalonica, the Byzantine crown jewel at the time. However, in 1423, just a year after the Ottomans put the blockade, the Byzantines handed over the defense of Thessalonica to Venice starting the first round of hostilities between Venice and the Ottomans. Venice matched all Ottoman attacks for 8 years despite much starvation and losses in their ranks. The Venetians were well trained and supplied launching several surprise attacks that steadily weakened the powerful Ottoman Navy. The standoff was also lengthened because of the small Ottoman army deployed in Macedonia at the time because Murad was fighting many other wars across Asia and Europe. In the late 1420s however, Murad was done with most battles allowing him to send his full force to Thessalonica finally taking the city.[11]

The Siege of Drepana – 8 Years

The battle for the control of Drepana, the Carthage capital from 264BCE to 146BCE was the ultimate determinant of Roman Dominance as the greatest power in the Mediterranean. Carthage was a wealthy trading empire boasting of a powerful navy and a large army with mercenaries while Rome was famous for the vast army that delivered great land and naval attacks. The Romans first marched on Drepana with a great force cutting off supplies both by land and sea, a blockade that dealt a big blow on the commerce dependent city. Things started poorly for the Romans with several defeats. The most significant loss for the Romans came in 249 when the whole Roman fleet led by Pontius Claudius Pulcher was totally destroyed at the hands of Drepania ships forcing the Romans to unlock the Naval trade routes to Drepana. They rebuild their fleet reinforcing it by 146. The Romans came back stronger fleet and finally launched a decisive attack on Drepana defeating the mercenary army to stamp their place in history.[12][13]

The Siege of Harlech Castle – 7 Years

This is the longest siege in British history starting on August 14th, 1461 to 1468 during the British wars of Roses when the Lancastrians fled to the refuge of the naturally impenetrable Harlech castle after being beaten by English Forces at the battle of Northampton. The castle was a natural haven that provided safety for the British royal family and especially Queen Margaret and Prince Edward from the constant attacks. It had been built in the 13th Century by King Edward I to be totally impenetrable and withstand any long siege. The castle had access to the sea which allowed the Lancastrians to access vital supplies and even French reinforcements via the sea. The 8-year blockade saw 50 men successfully repel several attacks from English forces until 1468 when King Edward finally commissioned 10,000 men to take the castle gaining entry to bring an end to the last Lancastrian Stronghold.[14][15]

The Siege of Xiangyang – 6 Years

Genghis Khan started the most extensive conquests in history But his son Kublai Han did the unthinkable! He conquered China! Under the Song Empire in the I3th Century, China was well fortified with walls and with a population of 70 million strong, they never expected anyone from beyond the wall to claim any part of their territory until the Mongols led came knocking on Xiangyang, South China. The Mongols placed a blockade on the fortified city pinning the Chinese inside but unable to impregnate the wall. The standoff went 5 for years until Kublai Khan borrowed Christian engineers from his eastern Europe relatives to help him built a catapult. With the power to fling 200lbs over 1000ft, The Mongols flattened parts of the wall in a cloud of dust in 1273 marking the first conquest of China by an invading force. It allowed Kublai Han to claim China and set up Beijing as his capital, a move that determined the shape of modern China.[16]

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