The Longest and Worst Sieges in history

The Longest and Worst Sieges in history

Larry Holzwarth - July 30, 2020

Merriam Webster’s Dictionary online defines the military tactic of a siege as, “a military blockade of a city or fortified place to compel it to surrender”. It is a process of war which is as old as recorded history, and which continues to the present day. Sieges are described in the Bible, in the stories of Homer, and in the histories of other ancients, such as Josephus and Tacitus. During the Second World War, several locations on the Eastern Front in Europe suffered epic sieges, including Stalingrad and Leningrad. The latter withstood a siege of nearly 900 days, one of the most gruesome in history.

The Longest and Worst Sieges in history
The siege and destruction of Jericho is one of many described in the Old Testament. Wikimedia

Siege warfare in history occurred in every continent of the globe. Some ended in extermination of the enemy after they surrendered, with all men and boys killed, and women enslaved by their conquerors, including some of the sieges described in the Bible. Others ended with the besieged achieving victory, though at staggering costs. Many included outbreaks of devastating diseases, such as typhus, smallpox, and cholera. Here are some of the longest sieges in history, and how they altered forever the region in which they took place.

The Longest and Worst Sieges in history
The SIege of Ceuta involved multiple enemies and over two decades of fighting. Wikimedia

1. The siege of Ceuta, 1694-1727

In the late 17th century, the city of Ceuta in Northern Africa was a Portuguese enclave, though its population was largely Moorish. During the period of Spanish-Portuguese union (1580-1640) its population gradually became dominated by the Spanish. In 1694, Moors under Muley Ismail, as part of their growing resistance to Spanish rule, attacked the outskirts of the city. It was the beginning of a siege which lasted more than thirty years, the single longest such military operation in modern history. Spanish, Portuguese, and Moroccan forces engaged each other in a series of conflicts which eventually drew in Dutch, British, and French troops and led to the English conquest of Gibraltar as a Mediterranean base.

Ceuta was nearly entirely razed by the long and mostly pointless siege, and the influence of the Portuguese was virtually eliminated from the region. Eventually, the Moors captured the city. Following the death of Muley Ismail, his sons’ infighting over their father’s estates and wealth led to the Moors abandoning the city to the Spanish. Largely rebuilt, Ceuta is a roughly 7 square mile autonomous Spanish city surrounded by Morocco, the Atlantic, and the Mediterranean Sea. Since the lengthy siege in the late 17th and early 18th century, it has enjoyed a mainly peaceful existence and is a cosmopolitan and culturally diverse community in the 21st century. It is home to Spaniards, Moroccans, and others of African descent, including Christians, Muslims, and Jews.

The Longest and Worst Sieges in history
An island fortress under Ottoman attack, believed to be a depiction of the Siege of Candia. Wikimedia

2. The siege of Candia, 1648-1669

Candia (today’s Heraklion, Crete) withstood a more than two-decade siege by forces of the Ottoman Empire, defended by Venetian troops and ships and the fabled Knights of Malta. Ottoman forces occupied most of Crete in 1648, as part of their expansion into the western Mediterranean. Hard-pressed Venetian forces opposed them. During the twenty-year siege of the Cretan capital, Venice found its power and influence waning, and Catholic France and Spain became the leading opponents of the Muslims. French troops went to the aid of the Venetians at Candia, but in 1669, after 21 years of bombardment and bloodshed, Candia surrendered to the Ottomans.

The siege is notable as one of the earliest recorded episodes of the use of germ warfare. The Catholic Venetians planned to attack the Muslim Ottomans using a serum extracted from the internal organs of plague victims. Venetian commanders hoped to weaken the Ottoman forces sufficiently to cause them to lift the siege. The plan was discovered by researchers in 2015, though there is no evidence that it was carried out. The Knights of Malta fought during the long siege, though unsuccessfully, and their waning influence and power was made apparent by the Ottoman victory. Candia remained under Ottoman control until the end of the 19th century.

The Longest and Worst Sieges in history
Ancient battlements at Thessalonica, a city conquered and sacked many times in history. Wikipedia

3. The Siege of Thessalonica, 1422-1430

During the expansion of the Ottoman Empire into western Europe, Venice underwent a decline in power in the Mediterranean region, as did the Byzantine Empire. In 1422, Byzantine control of the city of Thessalonica came under threat by the Ottomans, and political considerations placed control and defense of the region with the Venetians (there is a reason the word Byzantine today is used to describe something excessively complicated). The Venetians resisted the attacks and raids of the Ottoman forces for the ensuing eight years, despite losses of nearly 95% of the city’s population. The siege featured attacks from rebellious factions within the city as well as those of the Ottomans.

When the Ottomans finally captured the city by storm in late March, 1430, the conquering troops enjoyed three days of plundering, rape, and the enslavement of surviving civilians. Ancient monuments were destroyed, churches ransacked, and libraries and other evidence of culture destroyed. Formerly Christian churches were made into mosques. Only about 2,000 civilian residents of the city survived the siege, they were mostly converted to Islam by their conquerors. The city remained in Ottoman hands until the Greeks captured it during the Balkan War in 1912.

The Longest and Worst Sieges in history
Carthage was obliterated by the conquering Romans following a siege. Wikipedia

4. The siege of Carthage, 149-146 BCE

Carthage was a powerful empire in the Mediterranean region and northern Africa, built primarily upon sea power. Wealthy from its extended trading operations, the Carthaginians found natural rivals among the Berber tribes of North Africa, including the Numidians. They also found themselves in conflict with the growing Roman Republic, particularly over control of the settlements in what is Sicily today. A series of wars with the Romans, known as the Punic Wars, was the inevitable result of the rival empires and cultures. The Carthaginians also developed enemies among the tribes and settlements of the northern African regions they dominated, including today’s Libya and Tunisia.

Around 149 BCE Numidian tribes began seizing lands controlled by Carthage. The latter had largely disarmed itself as part of its treaty with the Romans following the 2nd Punic War. After entreating Rome for aid against the Numidians, Carthage again found itself at war with the Republic when the Romans ignored what was in essence a mutual defense arrangement and refused to intervene. The third Punic War found the Carthaginians fighting the Numidians and other Berber tribes as well as the armies of the Roman Republic, the latter led by Manius Manilius. It was, for lack of a better term, a very strange war to modern eyes.

The Longest and Worst Sieges in history
Rome took advantage of Carthage’s local difficulties to destroy their Mediterranean rival. Wikimedia

5. The surrender of Carthage, 149 BCE

When the Roman army arrived in North Africa, the Carthaginians quickly surrendered, delivering their weapons to the invaders and asking for terms. It also placed the commander of its armies, Hasdrubal, under arrest. The Romans made known their demands, which included the abandonment of the city of Carthage, and its inhabitants relocated to a new settlement. The city was then to be destroyed. Although some within the city supported complete surrender to the Romans, a larger faction advocated for resistance, and the disarmed Carthaginians rapidly rearmed themselves, preventing the Romans from entering the city.

The ensuing siege, which lasted three years, led to the deaths of about 450,000 Carthaginians. After Scipio Aemilianus became Roman consul, he pursued the siege doggedly, and the terms given to the survivors were harsh. About 50,000 Carthaginians survived the siege, only to enter enslavement under the Romans, and the city was razed to the ground. The siege and razing of Carthage was the first hostile act in what became the Roman Empire, as Roman expansionism across Northern Africa began. A new city, Roman Carthage, was created on the site, itself eventually sacked by Muslim forces in the 7th century CE.

The Longest and Worst Sieges in history
Solovetsky Monastery, Russia. Wikipedia

6. The Solovetsky Monastery Siege, 1668-1676

The Solovetsky Monastery, founded by Russian monks in 1436, occupied a strategically important position on Onega Bay in the White Sea region. In 1668, during a period of dissent and upheaval within the hierarchy of the Russian Orthodox Church in which the Tsarist government-enforced centralization, about 500 monks rebelled. The tsarist desire to enforce feudalism within the church and throughout Russia led to troops, known as Streltsy, arriving in June of 1668 to suppress the rebellious monks, who had the support of local peasants. The monks simply locked themselves into the fortified monastery, refusing to allow the Streltsy to enter. Local peasants and even some of the Tsarist troops kept the monks supplied with food.

For eight years the monks withstood the bombardment of the monastery, even expanding its defenses while besieged. In late 1675 a monk betrayed his fellow rebels, revealing a means of entering the monastery previously unknown to the besiegers, and the Tsarist troops entered the vast complex, butchering most of the occupants. Of the 500 or so monks and their families within, only about 60 survived. The monastery was later used by the communists as a part of the Soviet prison archipelago. Today, it is once again a monastery, re-established as such after the collapse of the Soviet Union, though it houses less than a dozen monks as of this writing, and serves primarily as a historical site and museum.

The Longest and Worst Sieges in history
The Crusaders built a massive fortress to besiege Tripoli. Wikimedia

7. The Siege of Tripoli, 1102-1109

The siege of the city of Tripoli refers to the Lebanese city of that name, not the Libyan city and port. It was besieged by Crusaders under Raymond IV of Toulouse who constructed a massive fortification outside the city, known as the Mons Peregrinus (Pilgrim’s Mountain). The presence of the fortress blocked food and other items from reaching Tripoli, and over the course of the next several years, Tripolitan forces and those of their allies made repeated attacks against the Frankish troops occupying the fortifications. In one such attack, in September, 1104, Raymond suffered serious wounds. He lingered until February before dying, during which period he negotiated a truce with Muslim leaders of the city.

The agreement was ignored by Raymond’s successors in command of the Crusaders, and in July, 1109, a reinforced Frankish force sallied forth from their mountain fortress and assaulted the weakened city. The Muslim defenders were defeated, and in celebration of their victory, the Crusaders thoroughly pillaged the city, exiling the few survivors they did not enslave. Tripoli remained in the hands of the Crusaders for the next 180 years, becoming a major producer of silk. It also provided citrus fruit and sugar to Europe. Today, Tripoli is the third-largest city in Lebanon, with a population which is primarily Muslim, though many churches erected by the Crusaders still stand.

The Longest and Worst Sieges in history
The Great Siege of Gibraltar was the longest military operation of what began as the American Revolutionary War. Wikimedia

8. The Siege of Gibraltar, 1779-1783

Gibraltar was held by the British in 1779, a year in which the American Revolutionary War became a global conflict. British occupation of the territory known as The Rock was a thorn in the side of the Spanish, and when Spain moved to support the Revolutionaries in North America it elected to reclaim the fortress and harbor at the gateway to the Mediterranean. The British resistance to the siege included daring runs into the harbor by ships of the Royal Navy, and despite several periods of severe shortages suffered by the troops and sailors, the British continued to resist Spanish efforts to oust them.

In 1782, after failing to capture Gibraltar for nearly three years, the Spanish received assistance from their French allies, who took over command of the operations. The French were no more successful than the Spaniards. The 43 and nearly a half month-long siege was the longest ever endured by the British Army in all its long history, and with the unflagging support of the Royal Navy, they prevailed over their attackers. Gibraltar has remained in British hands ever since, and serves as a major strategic naval base. Despite its status as a British Overseas Territory, Spain continues to claim the Rock as Spanish in the 21st century.

The Longest and Worst Sieges in history
The Mongol Empire destroyed the Song Dynasty following the Siege of Xiangyang. Wikimedia

9. Siege of Xiangyang, 1267-1273

In 1268, a Mongol army of about 100,000 men, supported by a fleet of more than 5,000 vessels, attempted to capture the twin cities of the Song Dynasty of Xiangyang and Fancheng. Both Song cities were heavily fortified, and the Mongols chose to surround them with fortified positions, gradually starving them into submission. Unknown to the Mongols was the vast amount of supplies previously stored in the cities, which held out against their enemies for years. The defenders also found a means of protecting themselves and the walls of the cities from the projectiles hurled by Mongol catapults. They fashioned nets to catch the projectiles, rather than allow them to strike their structures.

Both cities eventually fell to the Mongols in 1273, after several years of siege. Their losses hastened the end of the Song dynasty and extended Mongol influence to southern China. The two cities became one over the centuries, known as Xiangyang today, a major manufacturing center. A portion of the city wall which resisted the Mongol armies in the 13th century still stands. The siege was notable for its lengthy resistance to the Mongol forces and for the extensive casualties suffered by both sides, as well as for the use of a relatively new instrument of war – gunpowder.

The Longest and Worst Sieges in history
Harlech Castle, Wales. Wikimedia

10. Sieges of Harlech Castle

Harlech Castle, built from 1282-1289 in Wales by Edward I of England, occupies a promontory on the Irish Sea. During the Wars of the Roses, the castle was held by troops loyal to the House of Lancaster against the forces of the House of York for seven years. The ability to resupply the castle by sea gave the besieged an advantage, and the castle’s battlements were discouraging to those considering direct attacks. It became the last of the Lancastrian fortresses during the conflict before finally falling to the enemy in 1468, with the Yorkist troops supported by French allies. The end of the Wars of the Roses was marked by the ascension of the Tudors to the British throne.

It was again the site of a prolonged siege during the English Civil War, when forces supporting King Charles I occupied the castle. Since the siege nearly two centuries earlier the castle had fallen into disrepair. Its garrison, though small, attempted to refurbish the castle, but in 1647, after a nine-month siege, the men manning the fortress surrendered. The victorious forces of Parliament celebrated their triumph by partially destroying the nearly 400-year-old castle, creating the ruins as they exist today. Stones from several structures within the castle were re-used to build homes nearby.

The Longest and Worst Sieges in history
Spanish leader Cortes relied heavily on native allies during his conquest of Mexico. Wikimedia

11. The Siege of Tenochtitlan, 1521

Though not one of the longest sieges in history, few had further-reaching impact on the future of the world than the Spanish led conquest of the Aztec Empire. It culminated with the fall of Tenochtitlan, the Aztec capital, following a siege from May to August. The Spanish conquistadores under Hernan Cortes were but a small part of the victorious army, which was mostly comprised of native allies, including warriors from the Tlaxcala, Texcoco, Mixquic, and other peoples long subjugated by the Aztecs. Aided by an epidemic of smallpox, which decimated the Aztec people, the siege ended with a complete Spanish victory and the establishment of an empire in the New World which catapulted Spain into a world power.

Following the collapse of the Aztec defenses and the fall of the city, the native allies took revenge by slaughtering their enemies with abandon, looting, and pillaging. The Spaniards did not interfere with the continued attacks on the Aztecs, and whole villages and towns were destroyed in the genocide which did not spare women and children. As many as a quarter of a million Aztecs, warriors, civilians, women, and children, died as a result of the conquest, while Spanish casualties were around 100. The aftermath of the siege saw the complete destruction of the Aztec culture, and the establishment of a new city on the razed remains of their capital. Today it is known as Mexico City.

The Longest and Worst Sieges in history
The Siege of Vicksburg required coordinated operations between the Union Army and Navy. Wikimedia

12. Siege of Vicksburg. 1863

In May, 1863, Union forces under Ulysses S. Grant approached the Confederate stronghold at Vicksburg, an important rail and river junction which controlled access to the Mississippi. Despite outnumbering the Confederate defenders by about two to one, Grant’s probing of the formidable defenses led to his decision to capture the city by siege. The Confederate fortifications included rifle and cannon pits, redoubts, artillery placed so as to generate wide fields of fire, mortars and heavy guns, raised fortresses, and interconnecting trenches. The railroads leading into the city were well protected, allowing the Confederates to resupply both food and ammunition.

Grant probed the defenses in late May, accomplishing little other than casualties, before opening siege operations. Union troops dug trenches, moving them steadily closer to the Confederate positions during the month of June. Confederate troops underwent nightly heavy bombardment from Grant’s artillery and from naval gunships in the Mississippi River. The Navy alone fired well over twenty thousand shells into Vicksburg’s defenses and the city itself over the course of the siege. By the end of the month of June, about ten thousand of Vicksburg’s defenders – more than half – were unfit for duty due to sickness.

The Longest and Worst Sieges in history
Civilians attempted to escape the shelling by living underground. National Park Service

13. Civilians at Vicksburg lived under ground

To escape the ferocity of the combined Union bombardment, civilians within the Vicksburg perimeter abandoned their homes and moved underground. A long ridge ran along the Confederate lines, with the side facing the central portion of the city shielded from Union fire. Citizens dug caves in the side of the ridge, and some were furnished with items from their homes, including rugs, chairs, tables, and beds. As food supplies in the city dwindled, others remained in their homes, sheltered in cellars, in order to guard their vegetable gardens from starving Confederate troops. The Union troops concentrated their fire at Confederate defensive positions, though inevitably stray shells struck private homes and businesses.

The underground caves numbered over 500 during the month of June, and were easily seen by troops from many positions along the Union lines. Union soldiers called the ridge the Prairie Dog Village, its occupants by extension were called Prairie Dogs. Despite the ferocity of the bombardment few civilians fell to Union fire, though deaths from malnutrition and disease were high. Vicksburg fell to the Union on July 4, 1863. It was the same day Robert E. Lee’s Army of Northern Virginia began its retreat from Gettysburg, marking that Independence Day as the turning point of the American Civil War.

The Longest and Worst Sieges in history
The Siege of Sevastopol during the Crimean War previewed the destructive power of large, rifled cannon. Wikimedia

14. The Siege of Sevastopol, 1854-1855

The eleven month siege of Sevastopol represents one of the most revered moments in British military history, though it was hardly just a British operation against the Russian Empire. French, Sardinian, Egyptian, and Ottoman troops were involved as well, as were the French Navy. Eventually, German, Italian, Polish, and even Swiss troops joined in the attempt to capture the Black Sea port and end the Crimean War. The bulk of the troops defending Sevastopol were sailors of the Russian Navy, transferred from ships in the harbor which were scuttled to prevent Allied ships from penetrating the port. Command of the defenses was under three admirals of the Russian fleet, two of whom were killed in the siege.

On the Allied side, the French suffered the most casualties, with over 10,000 dead from combat, and over 50,000 from disease. In contrast, the British lost just under 5,000 to combat injuries, and about 16,000 to disease. Russian deaths exceeded 100,000. The fall of Sevastopol was the climactic event of the Crimean War, and in many ways foresaw events of the American Civil War. The siege saw the first use of railroads to move troops and supplies along the battlefront, and the first attempts to protect the sides of wooden ships with armor as they engaged in battle, through iron chains draped over the ships’ sides.

The Longest and Worst Sieges in history
The Siege of Ostend led to a Spanish victory which bankrupted the royal treasury. Wikimedia

15. Siege of Ostend, 1601-1604

The ability of sea power to affect military affairs on land was demonstrated dramatically by the over-three-year siege of Ostend, during a series of conflicts known collectively as the 80 Years’ War. The prolonged siege claimed the lives of over 100,000 soldiers, sailors, and civilians, and otherwise accomplished very little. The Dutch defending Ostend were resupplied, and reinforced, by sea, by their own ships and ships and troops from England. The Spanish attackers opened the siege in the summer of 1601 with a series of massive assaults, which were bloodily repulsed, after which the battle turned into one of attrition.

The British adopted the practice of assigning garrisons to the fortifications around Ostend for limited tours of duty before revolving them out. The practice helped minimize disease, often a weakening factor in besieged forces. By the time the Spanish finally took the city in September, 1604, there was a very little city left, it having been leveled by more than three years of continuous fighting. Technically the siege was a victory for the Spanish and a disheartening defeat for the Dutch, but its cost led to the Spanish court collapsing in bankruptcy three years later.

The Longest and Worst Sieges in history
French forces in Southeast Asia found the Vietnamese unwilling to capitulate in the mid-19th century, a lesson they failed to retain. Wikimedia

16. The Siege of Tourane, 1858-1860

In 1858, in response to the Vietnamese Emperor’s order to execute two Spanish Catholic missionaries the preceding year, French Emperor Napoleon III dispatched a joint Franco-Spanish expedition to chastise the Vietnamese ruler. In early September, the European forces seized Vietnamese fortifications on the Da Nang River, including the fortress of Tourane, which they promptly garrisoned. The bulk of the European forces then departed to attack Saigon. Once the French ships were gone from the Da Nang River, the Vietnamese promptly placed the garrisons under siege. There was relatively little fighting, and the Vietnamese adopted the strategy of denying supplies to the garrison, hoping to starve them into submission.

The French soon found themselves in a costly and frustrating quandary in Vietnam. They concentrated forces in one area only to find resistance arise in another. Pacifying the countryside proved to be an elusive goal. In early 1860, French commanders decided to concentrate their forces in the Saigon region, ignoring the smaller cities and hamlets. The garrisons at Tourane and around Da Nang were abandoned by the French, ending the almost two-year siege. The French lost 128 men in combat, and several hundred more to tropical diseases during the siege, before acknowledging the positions did little to further their overall situation in Vietnam.

The Longest and Worst Sieges in history
Turkilsh deserters photographed in Georgia during the Russo-Turkish War. Wikimedia

17. The Siege of Plevna, 1877

The Russo-Turkish War of 1877-78 was a result of the rising nationalism of the Balkan provinces and their desire for independence from the Ottoman Empire. They were supported by Russia, which desired recovery of territory lost through the Crimean War, and a re-establishment of their dominance of the Black Sea. The Russians established the ill-treatment of Christians in the Ottoman Empire as a casus belli, and a coalition force from Serbia, Montenegro, Bulgaria, Romania, and Russia attacked Turkish troops in the Balkans. With Constantinople threatened, Turkish forces held a fortified position at Plevna, forcing a siege of 145 days.

There was never much doubt as to the eventual outcome of the siege, with Russia and its allies fielding about 130,000 troops against fewer than 70,000 Turks and their allies. The siege was conducted, by the Turks, as a delaying action as its diplomats urged the western European powers to intervene. About 25,000 casualties were suffered by the Turks before they surrendered their positions in December, 1877. They inflicted about 50,000 casualties on the Russians. Though the siege resulted in Turkish surrender and a technical Russian victory, it was successful in buying the time for intervention by the west, primarily from the British Empire and its powerful fleet.

The Longest and Worst Sieges in history
Japanese 11 inch siege battery shelling Port Arthur. Wikimedia

18. The Siege of Port Arthur, 1904-1905

The largest land battle of the Russo-Japanese War, the siege of Port Arthur provided a glimpse of the fighting to be expected during the First World War one decade later. Machine gun nests, entrenchments topped with barbed wire, searchlights, control of troop movements by radio transmissions, electrically charged fences, rapid-firing light cannons, and bolt action magazine fed rifles all made their appearance. The Japanese believed they could capture the heavily fortified Russian positions at Port Arthur through a quick and decisive assault, instead, it took five months and a day. Port Arthur was heavily defended as a base for the Russian Pacific Fleet.

During the course of the siege, the fleet was destroyed by Japanese bombardment, though some ships were scuttled to prevent them from falling into Japanese hands. The Japanese suffered over 91,000 casualties during the siege, compared to about 31,000 for the Russians, though another 24,000 surrendered. The Russian defeat was a blow to the Tsar and created further unrest throughout much of the Russian Empire. The following year mutinies among military units, worker strikes, and other forms of protest led to constitutional reforms and a weakening of the Tsar’s grip over the Russian people.

The Longest and Worst Sieges in history
T. E. Lawrence gained fame as Lawrence of Arabia during the fight for Medina. Wikimedia

19. The Siege of Medina, 1916-1919

The Islamic Holy City of Medina was in the Ottoman Empire during the First World War, when it underwent the longest siege of that conflict. During the siege and other operations in the Arabian desert, Thomas Edward Lawrence gained enduring fame as Lawrence of Arabia. Sharif Hussein of Mecca sided with Lawrence and the British against the Caliph, besieging Arabian forces aligned with the empire in Medina. The forces which remained loyal to the empire and defended Medina were led by Fahreddin Pasha. The Arab revolt against Turkish rule was divided along tribal and religious lines, but with the Turks fighting alongside the Central Powers, it was in the interests of the British to encourage rebellion among the Arabs.

The Ottoman Empire withdrew from the war at the end of October, 1918. By then, the forces defending Medina had repulsed hundreds of attacks on the city and the railroad which connected it to supplies. Casualties on both sides were heavy throughout the siege, and bloodthirsty reprisals on prisoners and non-combatants were common. Following its exit from the war, the Ottoman Empire directed the remaining defenders of Medina to surrender. Pasha refused, and the city continued to hold out for more than two months. The garrison finally surrendered in January, 1919, after which Arab troops raided and pillaged the Turkish homes for two weeks. The total casualties during the long siege remain unknown, though Lawrence wrote of the heavy losses to both sides, including of women and children.

The Longest and Worst Sieges in history
Republicans dressed in the vestments of priests they murdered attest to the ferocity and atrocities of the Spanish Civil War. Wikimedia

20. The Siege of Madrid, 1936-1939

The siege of Madrid took place during the Spanish Civil War, between the factions supporting the Republic, and referred to collectively as Republicans, and the fascist Nationalists under Francisco Franco. After the Nationalists failed to capture the city in fierce battles in 1936, it came under a protracted siege. Italian and German bombers struck targets within the city’s defense lines throughout the siege, with air cover provided by fighter aircraft. It provided the first appearance in the battle of the new and modernized German Luftwaffe, alarming both the French and British air commands. The Italian efforts were somewhat less disconcerting.

Bitter divisions among the Republicans led to infighting among the leaders of the various factions, as the city continued to undergo bombing throughout 1937 and 1938. Franco’s Nationalists gradually tightened the noose around Madrid, adding artillery shells to the bombs, and the city’s civilian population suffered from starvation, disease, and the secret police executed suspected Nationalist sympathizers. Madrid’s defenses collapsed in March, 1939. Over the ensuing four years, Franco’s regime executed or imprisoned those who had opposed him, with over 200,000 dying in prison or executed outright. They can be added to the number of casualties of the siege, which have never been agreed upon by historians but were in the hundreds of thousands.

The Longest and Worst Sieges in history
Soviet anti-aircraft guns near St. Isaac’s Cathedral during the defense of Leningrad. Wikimedia

21. The siege of Leningrad, 1941-1944

The siege of Leningrad is often commemorated as the 900 days. It involved Finnish, German, and Soviet armies, the navies of Great Britain, Poland, the United States, Germany and the Soviets, and hundreds of thousands of civilians. It accounted for over 2 million military casualties among the armies, and an unknown, but brutally high number of civilian casualties. Soviet secret police (NKVD) records left reports of cannibalism, including the murder of individuals to use them as food. A division of Spanish troops, known as the Blue Division, served with the German Army during the siege, though officially Spain remained neutral throughout the war. The Soviets lost over 44,000 men against the Blue Division.

Leningrad was the target of the German Army Group North when Operation Barbarossa launched on June 22, 1941. Finnish troops entered the war to recover territory lost to the Soviets during the Winter War, and helped isolate Leningrad from the north, while the Germans advanced rapidly to the north and east. By early September, 1941, the Germans controlled all the roads entering Leningrad, effectively besieging it that month. Hitler made the reduction of Leningrad his first priority for the massive operations on the Eastern Front, and the Soviets fought with ferocity to prevent the city from falling into German hands.

The Longest and Worst Sieges in history
Leningrad endured over two years of near constant bombing and shelling. Russian International News Agency (RIAN)

22. Leningrad’s civilian population suffered throughout the long siege

On September 21 in Berlin, the OKW (the German High Command), made the fateful decision not to occupy Leningrad, but to destroy its population through starvation and bombardment. The decision was based on logistics. Occupation of a populated city by the Germans would place the responsibility of feeding the civilians on the Wehrmacht. The decision was made to starve the Soviets, allowing the Finns to enter the city if they chose to, and after the city capitulated the survivors were to be escorted into captivity deeper in Russia. Plans were made to demolish the city with explosives, bulldoze the rubble, and abandon the areas north of the Neva River to the Finns. On October 7, Hitler endorsed the plan.

Finnish plans did not include advancing on Leningrad, despite pleas from the Germans to do so throughout the siege. Nor did they bomb the city and its defenses, though German leaders implored them to do so. Finnish plans included the recovery of territory previously lost, with some advanced positions to consolidate defenses. The Finnish lines did isolate Leningrad, impeding Soviet attempts to supply the city and reinforce the troops defending the fortified region surrounding Leningrad. Beginning before the siege and continuing to March, 1943, Soviet troops fought to maintain a corridor through which to evacuate civilians from the city and its suburbs. Less than half of the prewar population of Leningrad were evacuated.

The Longest and Worst Sieges in history
Soviet anti-aircraft guns in Leningrad. Ammunition for defense took precedence over food for civilians. RIAN Archive

23. German aerial bombardment targeted civilian facilities

As it had during the siege of Madrid, the Luftwaffe targeted non-military areas in the city and its outlying suburbs. In September, 1941, the largest single air raid of the entire siege bombed hospitals, markets, bazaars, and the city’s open streets. Five hospitals alone were hit by German bombs. On some days, the Germans arrived in waves, with the bombing continuing throughout the long day. As had the Americans at Vicksburg, many Soviets turned to living underground. Throughout the siege, Russian Air Defense was in the hands of the navy fliers of the Baltic Fleet. Over 100,000 sorties by the navy fliers opposed the German air attacks, with heavy casualties on both sides.

In August, 1941, the Germans consolidated their positions around Leningrad’s defenses and heavy artillery added to the pounding of the city. The following year heavier guns arrived to continue the destruction. In both 1942 and 1943, the intensity of the bombardment and the weight of shells fired into the city increased from the preceding year. The German Army captured and looted several of the Imperial Palaces outside of the city, including the Peterhof and Catherine Palaces, with organized logistics trains carrying their art collections and other valuables Germany. Meanwhile, the Soviets organized a logistics system of their own, which became known as the Road of Life.

The Longest and Worst Sieges in history
German ammunition supply column before Leningrad. BildesArchiv

24. The Road of Life sustained the Russian defenses

A small strip of land remained within Soviet hands, connected to the southern part of Lake Ladoga, north of Leningrad. Hitler’s generals pleaded with the Finns to occupy it, though the Finns demurred over moving any closer to the city. It was the strip of land and the lake itself which provided Leningrad with a means of obtaining supplies, and evacuating the wounded and civilians. During the winter, trucks drove across the strip and across the frozen lake. During the summer, Russian boats crossed the lake, carrying the food and other supplies which kept the city alive. They returned bearing refugee civilians to safety. The lake was kept secure by a naval flotilla, the land section by Soviet troops. They were not secure from air attacks.

In December, 1941, after Soviet counterattacks strengthened their defensive positions, a short railroad was constructed along the Road of Life, allowing faster delivery of larger amounts of supplies to the city. In 1942 an oil pipeline was built along the corridor, which was called the Artery of Life and which provided badly needed oil. By 1943 Soviet attacks had pushed back the Germans to the point the supply route could be expanded and enlarged, and the area was more heavily defended with anti-aircraft guns. The Road of Life nonetheless operated for the most part during the winter months, with warm weather supplies being far outstripped by the winter operations.

The Longest and Worst Sieges in history
Soviet barges carrying supplies to besieged Leningrad across Lake Ladoga. RIAN Archive

25. The siege of Leningrad caused horrendous civilian casualties

According to some historians, the loss of civilian life in the siege of Leningrad equated to genocide. 1.5 million Soviet civilians and soldiers died during the siege, with most of the civilian deaths attributed to starvation. Over 1 million additional civilians died of starvation while being evacuated from the city. The siege was the worst in history in terms of the numbers killed. Well over 500,000 Germans were killed in the siege before the Germans withdrew in the face of Russian counterattacks beginning in January, 1944. NKVD records, finally released in 2004, indicated cannibalism was wider spread in the city of horrors than previously believed. In April 1942 alone, the NKVD arrested more than 300 civilians for cannibalism. The majority were women.

Most of the city was destroyed by the German aerial and artillery bombardment, its infrastructure left in ruins and its people decimated. The United States Military Academy at West Point published a study which estimated more Soviet casualties that occurred during the siege than those suffered by the combined British and American armies for the entire war, including those in the Pacific Theater of Operations. There have been sieges of longer duration before and since Leningrad, including that of Kosovo, but none approach it in terms of human cost. The city has since been entirely rebuilt, with some historic sites restored. It is today known once again as St. Petersburg, as it had been under the Tsars.


Where do we find this stuff? Here are our sources:

“The Spanish Enclaves in Morocco”. Robert Rezette. 1976

“Candia – 21 Years Under Siege Before Finally Surrendering”. Yulia Dzhak, War History Online. June 18, 2016

“Byzantium: The Roman Orthodox World, 1393 – 1492”. Anthony Bryer. 1998

“The Fall of Carthage”. Adrian Goldworthy. 2003

“A Tug of War Over Gulag History in Russia’s North”. Neil MacFarquhar, The New York Times. August 30, 2015

“History of the Crusades”. J. F. Michaud. 1852

“Gibraltar: The Greatest Siege in British History”. Lesley Adkins, Roy Adkins. 2017

“The Mongol Siege of Xiangyang and Fancheng and the Song Military”. Sandra Alvarez, De Re Militari. May 11, 2014. Online

“Harlech Castle”. Mark Cartwright, Ancient History Encyclopedia. November 28, 2019. Online

“Aztec capital falls to Cortes”. This Day In History, August 13.

“Vicksburg”. Article, American Battlefield Trust. Online

“The Crimean War”. Andrew Lambert, BBC History. March 29, 2011. Online

“The siege of Ostend and the Spinola offensives, 1601 – 1608. Weapons and Warfare. May 26, 2020. Online

“The Last Emperors of Vietnam: From Tu Duc to Bao Dai”. Oscar Chapuis. 2000

“Great Sieges of History”. William Seymour. 1991

“The True Story of Lawrence of Arabia”. Scott Anderson, Smithsonian Magazine. July 2014

“The Spanish Civil War”. Antony Beever, 2001

“The 900 Days: The Siege of Leningrad”. Harrison E. Salisbury. 1969